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$800

3 BR / 3 BA / Sleeps 10

1 Reviews

$800

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Beautifully water front Contemporary Home in Bay R

Annapolis house – 9.9 mi away
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill. Once you see the view from…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful Family House!

Left on Oct 17, 2013 for a stay in August 2013

We were fortunate to stay in this lovely home over Plebe Parent Weekend. It was perfect for our family of 6. There was plenty of room to spread out or come together for family time. The large dining table made us feel right at home. The bedding was fresh with new linens and towels in all the rooms. We enjoyed the lovely water views and great location. The Bay Ridge house is a short ride to the …

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$145

3 BR / 1 BA / Sleeps 7

1 Reviews

$145

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Chester River House with Views

Chestertown house – 18.6 mi away
3 BR / 1 BA / Sleeps 7 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in…
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

A PLEASANT STAY

Left on Aug 29, 2014 for a stay in August 2014

what a beautiful area of md. to stay at for an relaxing get away.the beautiful sun sets and sunrise.

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$110

1 BR / 1 BA / Sleeps 4

2 Reviews

$110

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Bayview by Chesapeake Bay

Chestertown house – 16.9 mi away
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

This cozy one-bedroom house is a wonderful spot for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Enjoy nature, birds - bald eagles, ospreys, blue herons - stunning sunsets and more by the bay. The one-bedroom house includes full kitchen, living room, bedroom…
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Patio
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Bayview cottage

Left on Jun 09, 2014 for a stay in June 2014

I stayed at Francesca's lovely Bayview cottage on the Chesapeake Bay in Tolchester, Maryland this weekend. The cottage is delightful, with porches on three sides, comfy beds, and a well appointed kitchen. After sleeping soundly, we awoke to the sight and sounds of songbirds in the yard and eagles, herons, and osprey flying over the Bay. Francesca is the perfect hostess!

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$250

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

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Charming Vintage Cottage/secluded Yard/Walk. WIFI

Annapolis cottage – 11.5 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks from Spa …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Great place. My dog loved the yard. I loved the Porch

Left on Jul 15, 2014 for a stay in December 2013

If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to grill a couple a steaks and have a semi barbeque (little cold so the porch was perfect) by eating and entertaining on the Porch.

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$95

1 BR / 1 BA / Sleeps 4

5 Reviews

$95

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Charming Apartment in Historic Chestertown, MD

Chestertown condo – 19.6 mi away
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An air mattress can be set up in the living room for 2 additional guests. An outdoor deck with cafe table and chairs is a …
  • Waterfront
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating

Details

Reviews

(5)

Cute little apartment right in Chestertiwn.

Left on Jun 05, 2014 for a stay in May 2014

The apartment in Chestertown is super cute and convenient. Walking distance to the water and all the cute cafés and restaurants. Clean and simple with a cute little balcony. The place was great and the hosts were helpful and responsive.

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$375

4 BR / 3 BA / Sleeps 10

1 Reviews

$375

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Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Saint Michaels house – 17.2 mi away
4 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and furnished for a comfortable …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect weekend getaway!

Left on Jan 10, 2014 for a stay in December 2013

My family recently spent a memorable weekend in December at Sandy Pines. We comfortably shared the house with a group of friends -- three other couples and their young children. The house has a lovely home-away-from-home feel. We especially enjoyed the wood-burning fireplace in the evenings.
Sandy Pines is perfectly situated -- a short drive from St. Michaels, and on a tranquil spot by the Bay…

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$175

3 BR / 2 BA / Sleeps 6

3 Reviews

$175

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Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Tilghman cottage – 18.6 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina on Knapps Narrows. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Relaxing weekend stay

Left on Mar 08, 2014 for a stay in March 2014

My husband and I spent a weekend at the Roost on Tilghman Island and it was so relaxing. We were really able to unplug and I slept better in their loft bedroom than I had in my own bed in weeks. The cottage was really sweet- it looks small on the outside but it's actually very spacious and I love how it was decorated. Everything was spotless and in good working order. We enjoyed the sun room/…

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$375

2 BR / 1 BA / Sleeps 6

1 Reviews

$375

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Cottage 2 at Grandview Pleasure Point

Bozman house – 17.3 mi away
2 BR / 1 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces, air …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful!

Left on Sep 30, 2013 for a stay in September 2013

Our family has been vacationing at Grandview for over 20 years. I think that says it all. Beautiful location, gorgeous sunsets, peaceful and quite. Serene. Plenty of crabbing, swimming, fishing and just plan relaxing. The cottages are nicely furnished, cozy, clean and well-stocked kitchen. Plenty to do in the area-close to St. Michaels, hiking, cycling, nice restaurants. We love it here.

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$665

4 BR / 3 BA / Sleeps 13

8 Reviews

$665

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Grandview Mainhouse

Bozman house – 17.3 mi away
4 BR / 3 BA / Sleeps 13 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch (2 queens, 1 double, daybed w/trundle, 5 twins) 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

relaxing

Left on Jun 24, 2011 for a stay in September 2010

A secret hideaway! We had never been to St. Michael's and even though this is out of town we like privacy. We stayed in one of the smaller units and it was perfect. Clean and updated with beautiful finishes. Would have loved to have a motor on the boat though!

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$280

4 BR / 2 BA / Sleeps 8

2 Reviews

$280

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Peaceful, Waterfront Home w/Pier on Kent Island

Chester house – 2.5 mi away
4 BR / 2 BA / Sleeps 8 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The location is serene on a 3 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Unbelievable value

Left on Nov 04, 2010 for a stay in May 2010

We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we…

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$350

3 BR / 2 BA / Sleeps 12

2 Reviews

$350

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Love Point Waterfront

Kent Island house – 4.1 mi away
3 BR / 2 BA / Sleeps 12 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Located on the Eastern shore of Maryland, Kent Island is a small area 13 miles long and 5 miles wide. The Bay Bridge spans the Cheasapeake bay from the Western shore to Kent Island. We are 4.5 miles north of the bridge in a charming old waterfront community called Love Point! Love Point is quiet area of single …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Home away from Home , We feel the weight of the world disappear when we walk through the door.

Left on Apr 17, 2015 for a stay in April 2015

Paula's Bay House is home away from home. like visiting the vacation house your family has had for years. You have a wall of windows view of the water. We spend hours just watching the birds and the waves. At night we stoke up the fire and gaze at the flickering flames and just be in the moment of quiet and peaceful relaxation. This house is warm and eclectic , has all the modern conveniences…

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$425

4 BR / 3 BA / Sleeps 9

2 Reviews

$425

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Beautiful Murray Hill Home (Annapolis)

Annapolis house – 11.9 mi away
4 BR / 3 BA / Sleeps 9 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking attention to detail to …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Comfortable and secure in a great home - almost as good as at ho

Left on Nov 03, 2013 for a stay in October 2013

The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town.

We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies.

We certainly will attempt…

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$250

3 BR / 2 BA / Sleeps 7

3 Reviews

$250

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* 3 Bedroom Rental House in Historic Rock Hall MD

Rock Hall house – 10.8 mi away
3 BR / 2 BA / Sleeps 7 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s Crab House, The …
  • Shared outdoor pool (unheated)
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

Excellent Value in a Great Location

Left on Apr 18, 2012 for a stay in May 2011

We have rented this home on several occasions over the past few years, and always found everything clean and in good working order. The large back yard is great for activities with our grandkids. Easy walking distance to Watermen's Restaurant and The Harbour Shack is a real bonus. Highly recommended!

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$750

6 BR / 5 BA / Sleeps 13

2 Reviews

$750

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Charming and Spacious Annapolis Victorian

Annapolis house – 12.3 mi away
6 BR / 5 BA / Sleeps 13 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms include a pool table …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Charming house in a great location! Perfect for larger group!

Left on Aug 11, 2014 for a stay in August 2014

We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large deck out back and patio furniture were wonderful for grilling and eating dinner outside. (The outdoor giant Jenga was a hit!) We went with a group of various couples and a couple of our single friends and everyone had …

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$350

7 BR / 4 BA / Sleeps 11

2 Reviews

$350

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Large Historic Home On Harbor in St. Michaels

Saint Michaels house – 14.0 mi away
7 BR / 4 BA / Sleeps 11 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and shops in St. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

This was the perfect home for a week of wedding planning and family relaxation time.

Left on Jul 23, 2014 for a stay in June 2014

Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time together finalizing wedding plans. The stay at the Harrison Home added so many memories to the already fond memories of a wedding. We cooked together with all the amenities in the kitchen. The home was so large we could …

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$295

3 BR / 3 BA / Sleeps 8

3 Reviews

$295

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Retreat at a quiet, water front cottage

Chestertown house – 11.1 mi away
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent County area. This south …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Construction in progress and mud everywhere.

Left on Oct 18, 2014 for a stay in October 2014

If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.

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$190

2 BR / 2 BA / Sleeps 4

1 Reviews

$190

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Premier Cottage in St. Michaels- In Town Location!

Saint Michaels house – 14.0 mi away
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor. The first floor of the…
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

I will never go back to the Jersey Shore Again!!!

Left on Aug 18, 2014 for a stay in August 2014

Location location location!

Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!

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$209

2 BR / 1 BA / Sleeps 6

1 / 11

$209

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Love Point Bay Vacation Home

Stevensville condo – 2.7 mi away
2 BR / 1 BA / Sleeps 6 | Quick view

Details

Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave your worries behind …
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $250

    3 BR / 2 BA / Sleeps 6

    1 / 23

    $250

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    TreeHouse

    Annapolis house – 9.9 mi away
    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped.
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $300

    1 BR / 1 BA / Sleeps 2

    1 / 9

    $300

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    2. Private 20 acre waterfront estate - studio apt

    Annapolis condo – 16.1 mi away
    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as the architect - …
    • Pet friendly - ask
    • Suitable for the elderly
    • Wheelchair accessible

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    $700

    5 BR / 6 BA / Sleeps 12

    1 / 6

    $700

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    Naval Academy Rental Home

    Annapolis house – 12.4 mi away
    5 BR / 6 BA / Sleeps 12 | Quick view

    Details

    Our home is brand new & only one block from the Naval Academy Stadium on Gibson Rd (you can see the stadium from M. bedroom balcony). With, 4 bedrooms upstairs & 1 bedroom down, all the bedrooms have their own full bath. There is also a family room on the second floor with a mini bar, sink & pull out sofa. The house …
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

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    $450

    3 BR / 3 BA / Sleeps 10

    5 Reviews

    $450

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    Beautiful St. Michaels House Steps from Water and Town

    Saint Michaels house – 14.2 mi away
    3 BR / 3 BA / Sleeps 10 | Quick view
    Excellent5 Reviews

    Details

    Reviews

    (5)

    Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath, second floor has one …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (5)

    Great Location, Great House, Great Time

    Left on Jul 13, 2014 for a stay in July 2014

    This house was perfect for a large family and very convenient for walking to sites in town. The house had a well equipped kitchen, nice backyard and barbecue grill. Within walking distance to local parks and public pool. We had nice holiday!

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    $350

    3 BR / 7 BA / Sleeps 10

    1 Reviews

    $350

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    WATERFRONT SUISSE CHALET

    Annapolis house – 9.8 mi away
    3 BR / 7 BA / Sleeps 10 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of West Annapolis and …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Great Stay, very nice location and clean home

    Left on Apr 09, 2015 for a stay in April 2015

    The home was located at a very continent location just 5-10mins drive to Naval academy and Annapolis downtown. The home was clean and have all the amenities. The water views from the house and easy access to the waterfront right behind the home make the stay even more memorable. I will recommend this place.

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    $200

    4 BR / 2 BA / Sleeps 8

    1 / 18

    $200

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    Snug Harbor USNA Cottage in Eastport Annapolis

    Annapolis house – 11.5 mi away
    4 BR / 2 BA / Sleeps 8 | Quick view

    Details

    The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue out back on the …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

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    $450

    3 BR / 2 BA / Sleeps 8

    1 / 7

    $450

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    Charming Townhouse - Steps to City Dock and USNA

    Annapolis house – 11.2 mi away
    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please note - the standard …
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $250

    3 BR / 2 BA / Sleeps 6

    2 Reviews

    $250

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    Waterfront Cottage at Spring Cove

    Rock Hall cottage – 11.6 mi away
    3 BR / 2 BA / Sleeps 6 | Quick view
    Very Good2 Reviews

    Details

    Reviews

    (2)

    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented to outdoor living …
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Laid back and relaxing

    Left on Aug 19, 2014 for a stay in August 2014

    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no expectations besides having a place to relax and hang out. We were very pleased. For a price similar to what we may have paid for one motel room elsewhere, the cottage suited our needs very well, with a fully equipped …

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    $180

    1 BR / 1 BA / Sleeps 4

    1 / 12

    $180

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    Captain's Quarters, a waterfront couples retreat

    Rock Hall condo – 11.5 mi away
    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and casual meals …
    • Pet friendly - ask
    • Suitable for children - ask

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    $250

    2 BR / 1 BA / Sleeps 4

    1 / 12

    $250

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    2 Bedroom Unique Private Waterfront Escape

    Easton condo – 12.6 mi away
    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to offer! The …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer

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    $595

    5 BR / 3 BA / Sleeps 20

    1 / 26

    $595

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    Annapolis Crows Nest Cottage: Chesapeake Bay View

    Annapolis villa – 11.0 mi away
    5 BR / 3 BA / Sleeps 20 | Quick view

    Details

    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden level, spa inspired …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

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    $295

    4 BR / 3 BA / Sleeps 8

    1 / 6

    $295

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    Downtown Annapolis !

    Annapolis house – 10.6 mi away
    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay Annapolis has to …
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $180

    2 BR / 2 BA / Sleeps 5

    12 Reviews

    $180

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    Location Location! St Michaels-- In Town Cottage!

    Saint Michaels house – 13.9 mi away
    2 BR / 2 BA / Sleeps 5 | Quick view
    Excellent12 Reviews

    Details

    Reviews

    (12)

    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor, believed to be one of two …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (12)

    Crabtastic Great Escape

    Left on Aug 26, 2011 for a stay in August 2011

    This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The building has been lovingly restored keeping to the historical accuracy, yet well placed modern conveniences make the stay even more enjoyable.

    I have visited this cottage several…

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    $350

    3 BR / 2 BA / Sleeps 6

    2 Reviews

    $350

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    *BOOK NOW* Beautiful Cottage in historic Annapolis

    Annapolis cottage – 11.2 mi away
    3 BR / 2 BA / Sleeps 6 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around with a minimum of …
    • Wireless Internet
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask

    Details

    Reviews

    (2)

    Visitor

    Left on Apr 13, 2015 for a stay in November 2014

    I had the pleasure of staying at this beautiful cottage for one night. It was very clean, comfortable, and had a really cozy ambiance. The neighborhood was quiet and peaceful and it's within minutes to the downtown area by foot or car. It felt just like home! I would definitely stay here again and highly recommend it to anyone interested.

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    $250

    3 BR / 4 BA / Sleeps 8

    1 Reviews

    $250

    Inquire

    ENDLESS SUNSETS - The perfect getaway!

    Claiborne house – 10.0 mi away
    3 BR / 4 BA / Sleeps 8 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake Bay. Every bedroom …
    • Waterfront
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Hard to find and worth the effort

    Left on Oct 10, 2014 for a stay in September 2014

    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and bathrooms galore. The only nitpick I have is the wifi seemed to fade in and out kicking us off regularly.

    But with such a great view and wonderful sunsets - you won't want to be on wifi anyway.

    Be sure to get good …

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    $375

    3 BR / 4 BA / Sleeps 6

    1 / 24

    $375

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    Charming Artists Home in Eastport/Annapolis

    Annapolis house – 10.8 mi away
    3 BR / 4 BA / Sleeps 6 | Quick view

    Details

    HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous restaurants, bars, coffee …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children - ask

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    $400

    2 BR / 2 BA / Sleeps 10

    1 / 23

    $400

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    Unique Accommodation for 10 in Annapolis, MD

    Annapolis cottage – 10.9 mi away
    2 BR / 2 BA / Sleeps 10 | Quick view

    Details

    ************* NEW LISTING - AVAILABLE NOW ************ SAILBOAT SHOW 2014 - $5000.00/wk POWER BOAT SHOW 2014 - $5000.00/wk CHRISTMAS 2014 - $5000.00/wk COMMISSIONING WEEK 2015 - $5000.00/wk Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen beds - 1 pull-out …
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $250

    4 BR / 3 BA / Sleeps 8

    1 / 17

    $250

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    Chez Cinquai

    Tilghman house – 18.4 mi away
    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet kitchen, custom wood …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

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    $262

    3 BR / 3 BA / Sleeps 8

    1 / 15

    $262

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    Oak View Ridge

    Maryland house – 18.8 mi away
    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Bedding: Queen, Queen, 2 Twins, Double Air Mattress Delightful enchantment is what you will experience the moment that you step inside the log home Oak View Ridge. The Great Room speaks of warmth and comfort with gorgeous hardwood floors and expansive vaulted ceilings. Cuddle up in front of a crackling fireplace or …
    • Fireplace
    • Parking
    • Grill
    • Television
    • DVD Player
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $350

    3 BR / 2 BA / Sleeps 8

    1 / 13

    $350

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    10 Union Street

    Annapolis house – 11.4 mi away
    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    N/A
    • Fireplace
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $759

    6 BR / 6 BA / Sleeps 12

    1 / 38

    $759

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    BayCottage Waterfront Vacation Retreat St.Michaels

    Saint Michaels villa – 13.1 mi away
    6 BR / 6 BA / Sleeps 12 | Quick view

    Details

    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are 6 bedrooms, 5.5 …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $450

    3 BR / 3 BA / Sleeps 8

    1 / 18

    $450

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    Historic Waterfront Property with Wi-Fi and Dock

    Saint Michaels house – 16.5 mi away
    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed with 2 twins beds and a…
    • Waterfront
    • Wireless Internet
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children

    PreviousNext property

    $350

    4 BR / 2 BA / Sleeps 10

    1 / 21

    $350

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    Easy access to Annapolis, Washington DC, Baltimore

    Arnold house – 13.0 mi away
    4 BR / 2 BA / Sleeps 10 | Quick view

    Details

    Clean, comfortable, family-friendly split-level home, fully furnished, washer and dryer, TV, cable, internet, wifi, quiet neighborhood with off-street parking, large shaded fenced back yard with deck for relaxing after a fun-filled day exploring Historic Annapolis, the Baltimore Harbor or our Nation's Capitol. #1BR-…
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

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      $550

      4 BR / 4 BA / Sleeps 14

      1 / 23

      $550

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      Chesapeake Bay Spectacular

      Stevensville house – 10.5 mi away
      4 BR / 4 BA / Sleeps 14 | Quick view

      Details

      Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes complete with …
      • Waterfront
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Washing Machine
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $450

      4 BR / 3 BA / Sleeps 10

      1 / 12

      $450

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      Chesapeake Bay Luxury Vacation Home, 5 Star

      Grasonville house – 2.7 mi away
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other accommodations do not. For large…
      • Waterfront
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Washing Machine
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $250

      2 BR / 2 BA / Sleeps 4

      1 / 8

      $250

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      Waterfront Boat Vacation Rental

      Davidsonville houseboat
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      2 bedroom, 2 bath with living salon, kitchen, and an aft deck
      • Waterfront
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for the elderly - ask

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      $300

      3 BR / 3 BA / Sleeps 6

      1 / 17

      $300

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      Annapolis Waterfront South River Chesapeake Bay

      Riva house – 16.3 mi away
      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      You'll love the stunning 180-degree view of the South River, just off the Chesapeake Bay near Annapolis. The location is incredible. Just six miles from Annapolis and the United States Naval Academy. The home is 15 miles from Baltimore/Washington International Airport and 40 minutes to Washington, D.C. (15 miles to …
      • Waterfront
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Washing Machine
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $257

      4 BR / 3 BA / Sleeps 10

      1 / 17

      $257

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      KI Golf House:A Par for the Course&Mile from Beach

      Kent Island house – 6.2 mi away
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      LOCATION…STAYCATION…GOLFCATION…right on Kent Island! KI Golf House: A Par for the Course Less than a mile to Dirty Dave's a gorgeous little beach and tiki bar. A short walk to the Chesapeake Bay. Call/email Donna and book it today! KI Golf House offers 4 Bedrooms, 2 ½ Baths, an open Kitchen Dining area…
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $280

      3 BR / 3 BA / Sleeps 6

      1 / 9

      $280

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      RESTORED WATERFRONT COTTAGE

      Saint Michaels cottage – 14.4 mi away
      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round vacationing. Our …
      • Waterfront
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $375

      4 BR / 4 BA / Sleeps 10

      1 / 37

      $375

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      Luxury vacation condominum with private beach

      Chester house – 1.6 mi away
      4 BR / 4 BA / Sleeps 10 | Quick view

      Details

      Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen size bed for the 4…
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $595

      3 BR / 3 BA / Sleeps 10

      1 / 24

      $595

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      Winter Rates Available Quiet Relaxing Waterfront

      Annapolis chalet – 11.3 mi away
      3 BR / 3 BA / Sleeps 10 | Quick view

      Details

      This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of West Annapolis and …
      • Waterfront
      • Internet Access
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $850

      4 BR / 4 BA / Sleeps 14

      1 / 24

      $850

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      Amazing Waterfront in Annapolis

      Annapolis house – 12.7 mi away
      4 BR / 4 BA / Sleeps 14 | Quick view

      Details

      A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the entire house 65' above the water. There are 4 full baths and 4 bedrooms with 2 kings, 2 …
      • Waterfront
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Washing Machine
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible
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