Annapolis

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$800

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Beautifully water front Contemporary Home in Bay R

Annapolis house
3 BR / 3 BA / Sleeps 10 | Quick view
Excellent1 Reviews

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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 …

$250

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Charming Vintage Cottage/secluded Yard/Walk. WIFI

Annapolis cottage
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 Creek. This…
  • 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.

$425

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Beautiful Murray Hill Home (Annapolis)

Annapolis house
4 BR / 3 BA / Sleeps 9 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

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

(3)

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…

$750

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Charming and Spacious Annapolis Victorian

Annapolis house
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 …

TreeHouse - Annapolis vacation rentals
1 / 23

$250

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TreeHouse

Annapolis house
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
2. Private 20 acre waterfront estate - studio apt - Annapolis vacation rentals
1 / 9

$300

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2. Private 20 acre waterfront estate - studio apt

Annapolis condo
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

$350

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WATERFRONT SUISSE CHALET

Annapolis house
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.

1 / 18

$200

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Snug Harbor USNA Cottage in Eastport Annapolis

Annapolis house
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
1 / 7

$450

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Charming Townhouse - Steps to City Dock and USNA

Annapolis house
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
1 / 26

$595

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Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa
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
1 / 6

$295

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Downtown Annapolis !

Annapolis house
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

$350

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*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

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

(3)

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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$375

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Charming Artists Home in Eastport/Annapolis

Annapolis house
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
1 / 23

$450

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Luxurious Annapolis Nautical Cottage

Annapolis cottage
2 BR / 2 BA / Sleeps 10 | Quick view

Details

Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen beds - 1 pull-out queen sleeper - 2 twins Unique Features - Walking distance to Naval Academy, downtown, shopping, restaurants and marinas - Shower for two - Off street parking for six - Completely renovated in …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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$850

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Amazing Waterfront Annapolis & easy walk downtown

Annapolis house
4 BR / 4 BA / Sleeps 14 | Quick view

Details

A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home and property: https://youtu.be/FBqOhPJZ-qU This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible
1 / 13

$450

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10 Minute Walk to Dwtn or Use Free Shuttle!

Annapolis house
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
1 / 24

$595

Inquire

Winter Rates Available Quiet Relaxing Waterfront

Annapolis chalet
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
1 / 14

$600

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Lavish Chesapeake Bay vacation Rental!!!!

Annapolis townhouse
1 BR / 2 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. With access to the beach to the beach and the own …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
1 / 12

$650

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Lavish and Upscale Vacation Rental

Annapolis apartment
1 BR / 3 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 …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Balcony or terrace

    $350

    Book

    *BOOK NOW* Beautiful Cottage in historic Annapolis

    Annapolis cottage
    3 BR / 2 BA / Sleeps 6 | Quick view
    Excellent3 Reviews

    Details

    Reviews

    (3)

    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 …
    • Internet Access
    • Fireplace
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating
    • Suitable for children - ask

    Details

    Reviews

    (3)

    Charming cottage walking distance to downtown Annapolis.

    Left on Mar 26, 2015 for a stay in March 2015

    My husband and I had a wonderful stay at this quiet cottage home. It is walking distance to downtown Annapolis. It was very clean and comfortable, we had a great night sleep on such a comfortable bed. The little side porch is so cute for morning coffee! The owners were right next door in case we had any questions and they were very helpful in pointing out restaurants and sights in the area. …

    1 / 15

    $450

    Book

    Downtown Annapolis Historic House

    Annapolis townhouse
    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    The house, built in 1878 by oyster packer Josiah Russell, has been owned by Campbell family members for at least four generations.On carpet, an elegant prayer rug is hung as a tapestry on a wall in the dining area. Chinese porcelain, cherished and collected by Jane and her parents, are displayed on tabletops and …
    • Outdoor Dining Area
    • Porch
      1 / 17

      $321

      Inquire

      Breathtaking Chesapeake Bay Waterfront

      Annapolis house
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      2,700 Sq. Ft. Of Casual Waterfront Elegance 50' From The Chesapeake Bay ! 2,700 sq. ft. of casual waterfront elegance 50' from the shores of the Chesapeake bay and 15 minutes from historic downtown Annapolis and the Naval Academy... You will be so close to the Chesapeake Bay that your view from the kitchen looks …
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Central heating
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

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