Chesapeake Bay

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$145

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Chester River House with Views

Chestertown house
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.

$134

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Hoopers Island Studio, 360 Degrees WATER VIEWS

Fishing Creek condo
1 BR / 1 BA / Sleeps 3 | Quick view
Excellent2 Reviews

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Reviews

(2)

360 Degree Views, WATERFRONT (Honga River) and WATERBACK (Chesapeake Bay)! Scenic, peaceful and spacious studio apartment located on the entire second floor of our property. AVAILABLE FOR 3 NIGHT STAY MINIMUM, sorry NO EXCEPTIONS ($375 per 3 night stay for 1-2 ppl, 3rd person $50 extra per stay) Ironman/Eagleman/…
  • Waterfront
  • Ocean or water views
  • Fireplace
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask

Details

Reviews

(2)

What a fantastic stay!

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

As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons.

Inside the house, we found all that we could need and more. The décor was adorable, though both aesthetically and functionally vintage. We found a very thoughtful welcome bag and bottle of wine on the dining table as soon …

$250

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Villa Wenona - Waterview Villa by Chesapeake Bay

Deal Island house
4 BR / 3 BA / Sleeps 12 | Quick view
Excellent7 Reviews

Details

Reviews

(7)

Property sleeps 10 with 4 bedrooms, 3 baths, living room, dining and sunroom. The majestic property of Villa Wenona sits on a beautiful lawn and wooded ¾ acre lot, yards from the Chesapeake Bay at the southern tip of Deal Island, MD. Enjoy exquisite sunsets from the comfortable sun room or the stunning balcony …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(7)

Very well equipped, clean, beautiful house and back yard includ

Left on Apr 15, 2013 for a stay in March 2013

We had a wonderful time. The owners are very friendly and prompt in responding with information to any question. The care takers next door are also very nice and helpful people. We will recommend this property to our friends any day!!!

$150

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1 bedroom cottage near water, dog friendly

North Beach cottage
1 BR / 1 BA / Sleeps 5 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full kitchen, and a backyard …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Quiet and peaceful!

Left on Sep 26, 2011 for a stay in September 2011

We had a very nice stay at Seahorse cottage. It was on a quiet street, but only a short walk to the boardwalk. The owners are wonderful to talk to. We hope to go back next year for our anniversary.

$120

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Bayview by Chesapeake Bay

Chestertown house
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent2 Reviews

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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
  • Porch
  • 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!

$95

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Charming Apartment in Historic Chestertown, MD

Chestertown condo
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent5 Reviews

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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.

    $375

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    Sandy Pines: Enjoy Harris Creek w/Pool and Boats

    Saint Michaels house
    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…

    1 / 9

    $250

    Book

    Renovated Luxury Waterview House

    North Beach house
    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to beach, boardwalk, …
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    1 / 21

    $125

    Book

    Captain's Watch Vacation Cottage

    Tilghman cottage
    2 BR / 1 BA / Sleeps 6 | Quick view

    Details

    Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on the Eastern Shore. …
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    $175

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

    Tilghman cottage
    3 BR / 2 BA / Sleeps 6 | Quick view
    Excellent4 Reviews

    Details

    Reviews

    (4)

    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

    (4)

    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/…

    $375

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    Cottage 2 at Grandview Pleasure Point

    Bozman house
    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.

    $665

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    Grandview Mainhouse

    Bozman house
    4 BR / 3 BA / Sleeps 13 | Quick view
    Excellent9 Reviews

    Details

    Reviews

    (9)

    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

    (9)

    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!

    $280

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    Peaceful, Waterfront Home w/Pier on Kent Island

    Chester house
    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…

    $1,100

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    Yr Round Estate on Bay / Family Reunions Sleeps 28

    Cambridge villa
    7 BR / 6 BA / Sleeps 28 | Quick view
    Excellent5 Reviews

    Details

    Reviews

    (5)

    Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates up to 28 people and …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Great hospitality...

    Left on Apr 24, 2012 for a stay in April 2012

    The house is well decorated and spacious, fantastic for family gatherings. We had a great experience that will be remembered for the rest of our lives.

    This property had all you needed for a great family vacation, but above all, the owner is a master of hospitality - he was very accommodating to every request we had.

    I hope to go back to this house for another week soon.

    $1,200

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    Yr Round Waterfront Home w/ Dock & Pool - Slps 18

    Cambridge house
    5 BR / 4 BA / Sleeps 18 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large outdoor grill. The …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Dream vacation

    Left on Oct 18, 2012 for a stay in August 2012

    We spent a week a Swan cove. the entire Family loved the house. Very spacious, clean and the kids had a blast in the pool. Great setting with the private dock, fire pit, playground just an amazing home.
    We already reserved for next year!!!

    $449

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    Waterfront Chespeake Bay Retreat

    Cambridge house
    7 BR / 5 BA / Sleeps 18 | Quick view
    Excellent11 Reviews

    Details

    Reviews

    (11)

    New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal for large family …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (11)

    Wondeful home - Great for Fishing!

    Left on May 04, 2009 for a stay in April 2009

    We had an amazing week at this gorgeous house. The house is brand new and immaculate. Everything in it is brand new!! It truly felt like home. The owners are amazing - it was a warmer week than expected and they went out of their way to open the pool for us. They also gave a lot of great recommendations on places to eat. We took out the boat and the kids had a great time fishing and …

    $449

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    Stunning, Newer Chesapeake Waterfront Rental

    Cambridge house
    6 BR / 5 BA / Sleeps 16 | Quick view
    Excellent9 Reviews

    Details

    Reviews

    (9)

    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge, Easton, Oxford & St. …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (9)

    GREAT Vacation!

    Left on May 05, 2009 for a stay in August 2008

    We really had a GREAT stay. The house is much more than we expected; it's very well done and comfortable (the owner was nice as well). The water views are amazing and the grounds perfect. We swam, fished, crabbed, biked and boated - had a great time off property as well. This was a TOP notch vacation.- thanks!

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    $150

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    Chesapeake Bay Sunrises AND Sunsets

    Westover house
    2 BR / 1 BA / Sleeps 6 | Quick view

    Details

    Located in Frenchtown, MD, 30 min south of Salisbury, MD on Chesapeake Bay's Eastern Shore. This is a private home on an island in the middle of ten thousand acres of salt marsh and near a national wildlife management area. Views from the bedroom, enjoy waterfront sunrises, water views from the living room & dining …
    • Waterfront
    • Ocean or water views
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly

    $500

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    Chesapeake Bay Waterfront, Private Dock, Beach

    Cambridge house
    6 BR / 3 BA / Sleeps 18 | Quick view
    Excellent6 Reviews

    Details

    Reviews

    (6)

    The Swan's Nest in Cambridge, Maryland, has all that the Chesapeake Bay has to offer: sun, sand, fishing, crabbing, a par 3 golf course on site and so much more. The spacious and lovingly restored farmhouse can accommodate 18 guests. The kitchen is fully equipped and a barbeque pit is just outside on the patio. …
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Internet Access
    • Fireplace
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Fantastic Bay Experience!

    Left on Jul 16, 2012 for a stay in July 2012

    My extended family (12 plus part week guests) just got back from a week at Swan's Nest. Hap was a fantastic host and tried really hard to ensure we had what we needed for the needs and interests of our group. I can't say enough about his personal involvement and patience in answering our questions.

    It was a fantastic experience - we went crabbing - a lot - we brought supplies to run a trot …

    $295

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    Retreat at a quiet, water front cottage

    Chestertown house
    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.

    $190

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    Premier Cottage in St. Michaels- In Town Location!

    Saint Michaels house
    2 BR / 2 BA / Sleeps 4 | Quick view
    Excellent2 Reviews

    Details

    Reviews

    (2)

    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

    (2)

    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!

    $350

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    Large Historic Home On Harbor in St. Michaels

    Saint Michaels house
    7 BR / 4 BA / Sleeps 11 | Quick view
    Excellent6 Reviews

    Details

    Reviews

    (6)

    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

    (6)

    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 …

    $225

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    Cobb Island Waterfront Home with Beach & Dock

    Cobb Island house
    4 BR / 2 BA / Sleeps 9 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Welcome to our Cobb Island, Maryland Home, on the waterfront in Southern Maryland, one hour from Washington D.C. - the perfect spot to spend your next relaxed family vacation enjoying water oriented activities and fabulous river views. We have been renting this house to more than 200 families since 1999 and have many…
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Great Waterfront Rental for families and groups of friends

    Left on Dec 28, 2011 for a stay in July 2010

    I only have great things to say about Ed Mullan's Cobb Island rental.
    Having stayed there for several weekends, I can attest to the
    comfortable and well-appointed house, fantastic location close to
    Washington, DC, and abundance of fun activities at the house and
    surrounding area. The property is ideal for families as well as groups of friends. Both the indoor and outdoor areas are conducive for …

    $450

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    Beautiful St. Michaels House Steps from Water and Town

    Saint Michaels house
    3 BR / 3 BA / Sleeps 10 | Quick view
    Excellent6 Reviews

    Details

    Reviews

    (6)

    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

    (6)

    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!

    1 / 4

    $575

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    Red Point Lighthouse

    North East house
    4 BR / 4 BA / Sleeps 8 | Quick view

    Details

    Custom lighthouse with 4 bedrooms and 4 baths overlooking the Chesapeake Bay. Within one hour from Baltimore, MD, Wilmington DE, and Lancaster, PA. Perfect for large families, weddings, ect.
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Fireplace
    • Washing Machine
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    $250

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    Unique, Affordable Nature-Oriented Getaway Home

    Cambridge house
    3 BR / 2 BA / Sleeps 6 | Quick view
    Average1 Reviews

    Details

    Reviews

    (1)

    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide covered front porch and …
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Nice house but it is not on the water

    Left on Oct 26, 2012 for a stay in July 2012

    This is a lovely older house with lots of room for families. We are very grateful that she accepts dogs and even better that the house is so clean you can't tell that dogs have stayed there. The electronics are a bit old but useable and there is no wifi. There are bikes available for use and the area would be great for bike riding but in July when we were there it was over 100 every day and …

    1 / 10

    $250

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    Relaxation At Its Best!!!!

    North East house
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Come vacation in this brand-new home in beautiful Elk Neck and you will be glad you did! It is definitely a most gorgeous location and very peaceful, set back in the woods along the river. Elk Neck is approximately eight miles south of the town of North East, MD where there are many neat little shoppes and fabulous …
    • Waterfront
    • Ocean or water views
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly - ask
    1 / 20

    $240

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    2 Bedroom Unique Private Waterfront Escape

    Easton condo
    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

      $180

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      Location Location! St Michaels-- In Town Cottage!

      Saint Michaels house
      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…

      1 / 17

      $250

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      Chez Cinquai

      Tilghman house
      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
      1 / 38

      $759

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      BayCottage Waterfront Vacation Retreat St.Michaels

      Saint Michaels villa
      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
      1 / 18

      $450

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      Historic Waterfront Property with Wi-Fi and Dock

      Saint Michaels house
      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
      1 / 20

      $159

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      Best kept secret by the bay (Entire House)

      Fishing Creek house
      3 BR / 2 BA / Sleeps 5 | Quick view

      Details

      Hooper's Island is located between the Honga River and Chesapeake Bay on Marylands Eastern Shore. This unique island is a "MUST DO" on your bucket list. Especially noted for: Maryland's famous Blue Crabs and Breathtaking Sunsets!!! April thru October on Hooper's Island is must do on your bucket list as you …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Fireplace
      • Housekeeping Optional
      • Suitable for children - ask
      1 / 37

      $375

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      Luxury vacation condominum with private beach

      Chester house
      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
      1 / 12

      $250

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      Million dollar view on the Chesapeake

      Deale house
      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Fredelig sted"(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you arrive. Watch the seagulls or osprey …
      • Waterfront
      • A/C or climate control
      • Porch
      • Parking
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask
      1 / 9

      $280

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      RESTORED WATERFRONT COTTAGE

      Saint Michaels cottage
      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
      1 / 41

      $190

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      "The Cottage" Cambridge Chesapeake Waterfront Home

      Cambridge cottage
      3 BR / 1 BA / Sleeps 5 | Quick view

      Details

      "The Cottage" at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch or soak in the 450 gallon hot tub. Fish and …
      • Waterfront
      • Hot Tub/Jacuzzi
      • A/C or climate control
      • Central heating
      • Deck
      • Suitable for children - ask
      • Suitable for the elderly - ask
      1 / 6

      $190

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      Historic Chestertown, pet-friendly

      Chestertown cottage
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Our Victorian cottage, built in the 1880s and upgraded to more modern standards, offers the best of both worlds: A bit of a rural feel, with a fenced-in side yard and back yard, a lovely porch swing, and ... easy strolling distance to the downtown historic Chestertown. Did you know that the fabulous Garden and Gun …
      • Wireless Internet
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask

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