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$750

6 BR / 5 BA / Sleeps 13

2 Reviews

$750

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Charming and Spacious Annapolis Victorian

6 BR / 5 BA / Sleeps 13 | Quick view
“ Excellent ” 2 Reviews

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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
  • A/C or climate control
  • Central heating
  • Deck
  • 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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$225

3 BR / 3 BA / Sleeps 7

My Seaside Cottage and La Petite Maison - Annapolis vacation rentals
1 / 18

$225

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My Seaside Cottage and La Petite Maison

3 BR / 3 BA / Sleeps 7 | Quick view

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My Seaside Cottage and La Petite Maison Located on beautiful, secluded North Beach of Current, Eleuthera, our 2-bedroom cottage is situated in the vicinity of the quaint settlement of Current, Eleuthera population 130, an ideal getaway from the hustle and bustle of 21st Century living. A 10 minute drive to the ferry …
  • Waterfront
  • Parking
  • Grill
  • Towels Provided
  • Microwave
  • 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

3 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

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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

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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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$647

5 BR / 5 BA / Sleeps 14

Rest Assured - Annapolis vacation rentals
1 / 25

$647

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Rest Assured

5 BR / 5 BA / Sleeps 14 | Quick view

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Bedding: King, Queen, Queen, 2 Bunkbeds, 2 Bunkbeds Be “Rest Assured” that you will have a truly magical Deep Creek experience when you choose to stay in this fabulous 5 bedroom lakefront home. Evidently furnished and designed with a great deal of love and pride, you will quickly fall in love with all of the …
  • Ocean or water views
  • Fireplace
  • A/C or climate control
  • Television
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$169

3 BR / 2 BA / Sleeps 4

2 Reviews

$169

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Spacious, Modern Condo nr. Navy Stadium and Mall

3 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has twin beds. Large loft has queen size bed. Although the condo can accommodate 6 for sleeping, I will rent only to parties of 4 or fewer. Dining room can seat 8 + Washer and Dryer, ironing board. Microwave…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Suitable for children

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Reviews

(2)

Great place, great location and great price

Left on Nov 12, 2013 for a stay in November 2013

My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a family of four. We took a chance on this condo and it was awesome. It was less expensive than a hotel room and we each had our own room and could cook our own meals. The location had easy access to the football game, the…

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$490

5 BR / 3 BA / Sleeps 13

Upscale House/12 MINUTES FROM DC - Annapolis vacation rentals
1 / 25

$490

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Upscale House/12 MINUTES FROM DC

5 BR / 3 BA / Sleeps 13 | Quick view

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Beautiful, comfortable single-family house located in the exclusif and upscale dunbarton community. Easy access to many attractions including Six Flags, HurrIcane Harbor, golf courses, walking paths, Forest PARK national preserve, the redskins FEDEX FIELD, historicDC, FAMOUS MAGIC JOHNSON'S BOULEVARD( RESTAURANTS, …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

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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

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

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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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$450

3 BR / 2 BA / Sleeps 8

1 / 7

$450

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Charming Townhouse - Steps to City Dock and USNA

3 BR / 2 BA / Sleeps 8 | Quick view

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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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$575

4 BR / 4 BA / Sleeps 14

1 / 23

$575

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Chesapeake Bay Spectacular

4 BR / 4 BA / Sleeps 14 | Quick view

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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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$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

4 BR / 3 BA / Sleeps 10 | Quick view

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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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$350

3 BR / 2 BA / Sleeps 6

1 Reviews

$350

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*BOOK NOW* Beautiful Cottage in historic Annapolis

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

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 …
  • Wireless Internet
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask

Details

Reviews

(1)

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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$209

2 BR / 1 BA / Sleeps 6

1 / 11

$209

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Love Point Bay Vacation Home

2 BR / 1 BA / Sleeps 6 | Quick view

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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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    $850

    4 BR / 4 BA / Sleeps 14

    1 / 24

    $850

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    Amazing Waterfront in Annapolis

    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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    $180

    1 BR / 1 BA / Sleeps 4

    1 / 12

    $180

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    Captain's Quarters, a waterfront couples retreat

    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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    $375

    4 BR / 3 BA / Sleeps 10

    1 Reviews

    $375

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    Sandy Pines: Enjoy Harris Creek w/Pool and Boats

    4 BR / 3 BA / Sleeps 10 | Quick view
    “ Excellent ” 1 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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    $200

    4 BR / 2 BA / Sleeps 8

    1 / 18

    $200

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    Snug Harbor USNA Cottage in Eastport Annapolis

    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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    $759

    6 BR / 6 BA / Sleeps 12

    1 / 38

    $759

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    BayCottage Waterfront Vacation Retreat St.Michaels

    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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    $164

    3 BR / 2 BA / Sleeps 8

    1 / 49

    $164

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    Fun DC/Annaoplis Chesapeake Waterfront Cottge

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    This 3 bedroom/2 bath cottage is just the spot for a get-away with other couples or your entire family! Nestled on 2 country-like acres in a surprisingly convenient corner of the Chesapeake Bay, this unique area is just over 20 minutes south of Annapolis and 45 minutes from Wash DC, Alexandria VA, or Baltimore. …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Washing Machine
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $222

    4 BR / 3 BA / Sleeps 10

    1 / 22

    $222

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    Marshall Haus

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    Marshall Haus Travel to a unique comfortably furnished round house in a secluded Caribbean paradise, featuring excellent snorkeling, fishing, and diving from a mile long white powder sand beach. Located in the vicinity of the quaint settlement of Current, Eleuthera population 130, an ideal getaway from the hustle and …
    • Waterfront
    • Internet Access
    • Washing Machine
    • Parking
    • Grill
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $1,500

    4 BR / 4 BA / Sleeps 10

    1 / 15

    $1,500

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    1. Private 20 acre waterfront estate - main house

    4 BR / 4 BA / Sleeps 10 | Quick view

    Details

    Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation and building addition with exposed structure and mechanical systems that serves as the architect - owner's live-work getaway. The main house has a 4 stop elevator, 2 car garage, master bdrm and bath suite, 3 additional large bedrooms, and …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

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    $250

    4 BR / 3 BA / Sleeps 10

    1 / 12

    $250

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    Million dollar view on the Chesapeake

    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

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    $250

    3 BR / 4 BA / Sleeps 8

    1 Reviews

    $250

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    ENDLESS SUNSETS - The perfect getaway!

    3 BR / 4 BA / Sleeps 8 | Quick view
    “ Excellent ” 1 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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    $250

    2 BR / 2 BA / Sleeps 4

    1 / 8

    $250

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    Waterfront Boat Vacation Rental

    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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    $350

    3 BR / 7 BA / Sleeps 10

    1 / 22

    $350

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    WATERFRONT SUISSE CHALET

    3 BR / 7 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
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Fireplace
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $150

    1 BR / 1 BA / Sleeps 5

    5 Reviews

    $150

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    1 bedroom cottage near water, dog friendly

    1 BR / 1 BA / Sleeps 5 | Quick view
    “ Excellent ” 5 Reviews

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    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.

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    $425

    4 BR / 3 BA / Sleeps 9

    2 Reviews

    $425

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    Beautiful Murray Hill Home (Annapolis)

    4 BR / 3 BA / Sleeps 9 | Quick view
    “ Excellent ” 2 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 6

    1 / 9

    $250

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    Renovated Luxury Waterview 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

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    $247

    3 BR / 3 BA / Sleeps 8

    1 / 15

    $247

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    Oak View Ridge

    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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    $262

    4 BR / 4 BA / Sleeps 11

    1 / 11

    $262

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    Sunrise Cove

    4 BR / 4 BA / Sleeps 11 | Quick view

    Details

    Bedding: King, Queen, Bunk w/trundle, Double, QSS, TSS Create unforgettable moments with family and friends when you stay in the delightful 4 bedroom lake access home Sunrise Cove. This stunning home, with its stylish décor and open floor plan, boasts the ultimate in comfort and relaxation. Fall in the love with the …
    • Ocean or water views
    • Fireplace
    • A/C or climate control
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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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

    4 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 2 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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    $300

    3 BR / 3 BA / Sleeps 6

    1 / 17

    $300

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    Annapolis Waterfront South River Chesapeake Bay

    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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    $500

    4 BR / 4 BA / Sleeps 8

    1 / 13

    $500

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    10 Minute Walk to Dwtn or Use Free Shuttle!

    4 BR / 4 BA / Sleeps 8 | Quick view

    Details

    NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac neighborhoods and features …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Deck
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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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

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 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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    $487

    6 BR / 3 BA / Sleeps 16

    1 / 4

    $487

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    Duck Cove at Wisp

    6 BR / 3 BA / Sleeps 16 | Quick view

    Details

    Community: Lake Pointe Bedding: King, Queen, Queen, Queen, Queen, 2 Twins, 2 Queen Sleeper Sofas Dove Cove at Wisp offers prime location, the most desirable amenities and the promise for an extraordinary Deep Creek vacation! Located in the prestigious community of Lake Pointe at Wisp, this home will put you in the …
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Fireplace
    • A/C or climate control
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $350

    3 BR / 2 BA / Sleeps 12

    1 / 13

    $350

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    Love Point Waterfront

    3 BR / 2 BA / Sleeps 12 | Quick view

    Details

    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

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    $375

    4 BR / 4 BA / Sleeps 10

    1 / 37

    $375

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    Luxury vacation condominum with private beach

    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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    $450

    4 BR / 3 BA / Sleeps 10

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    $450

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    Chesapeake Bay Luxury Vacation Home, 5 Star

    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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    $650

    1 BR / 6 BA / Sleeps 6

    1 / 14

    $650

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    Lavish Chesapeake Bay vacation Rental!!!!

    1 BR / 6 BA / Sleeps 6 | Quick view

    Details

    This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. The security guard at the booth adds a feeling of …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Suitable for children

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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!

    2 BR / 2 BA / Sleeps 5 | Quick view
    “ Excellent ” 12 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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    $190

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $190

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    Premier Cottage in St. Michaels- In Town Location!

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 1 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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    $350

    4 BR / 2 BA / Sleeps 10

    1 / 21

    $350

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    Easy access to Annapolis, Washington DC, Baltimore

    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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      $249

      2 BR / 2 BA / Sleeps 5

      1 / 17

      $249

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      Chesapeake Bay House

      2 BR / 2 BA / Sleeps 5 | Quick view

      Details

      Outstandingly beautiful and immaculately maintained light-filled custom-built home with stunning, unobstructed views of the wonderful Chesapeake Bay in the picturesque town of North Beach. Steps away from the boardwalk in front of the bay. Within a 45-min drive from Washington DC (just 33 miles), Baltimore & Annapolis…
      • Waterfront
      • Hot Tub/Jacuzzi
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask

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      $250

      3 BR / 2 BA / Sleeps 6

      1 / 23

      $250

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      TreeHouse

      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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      $175

      3 BR / 2 BA / Sleeps 10

      10 Reviews

      $175

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      Ocean City, MD - Time n Tide Unit #1 (OCEAN BLOCK)

      3 BR / 2 BA / Sleeps 10 | Quick view
      “ Excellent ” 10 Reviews

      Details

      Reviews

      (10)

      OCEAN CITY, MARYLAND: 26th St - Steps to beach w/POOL (RENT TO HIGH SCHOOL SENIORS) The Time-n-Tide building is located at the quiet end of the boardwalk in Ocean City, Maryland. Condo has an unblocked southern exposure and the BEACH and BOARDWALK is less than 200 yards from the front door. The complex has a fenced …
      • Shared outdoor pool (unheated)
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (10)

      Great Getaway Place

      Left on Jun 23, 2011 for a stay in May 2011

      We rented the unit for a family re-union. The three bedrooms were spacious and everything in the place was brand new. Of all the places we looked at in OC this one had everything we were looking for. It was only one block to the beach, had ample parking, great front porch with plenty of room to eat outside and the owners couldn't do enough for us. The whole complex with it's pool and fenced in …

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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

      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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      $350

      3 BR / 2 BA / Sleeps 8

      1 / 5

      $350

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      10 Union Street

      3 BR / 2 BA / Sleeps 8 | Quick view

      Details

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

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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 Ridge, Annapolis

      3 BR / 3 BA / Sleeps 10 | Quick view
      “ Excellent ” 1 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 …
      • 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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      $250

      3 BR / 2 BA / Sleeps 7

      3 Reviews

      $250

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      * 3 Bedroom Rental House in Historic Rock Hall MD

      3 BR / 2 BA / Sleeps 7 | Quick view
      “ Excellent ” 3 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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      $295

      4 BR / 3 BA / Sleeps 8

      1 / 6

      $295

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      Downtown Annapolis !

      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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      $300

      1 BR / 1 BA / Sleeps 2

      1 / 9

      $300

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      2. Private 20 acre waterfront estate - studio apt

      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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