Holiday Rentals in Annapolis
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The best holiday rentals in Annapolis
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Gaia House
Featuring air-conditioned accommodation with a patio, Gaia House is located in Annapolis. This property offers access to a balcony, free private parking and free WiFi.
Inn on Main Annapolis
Set within 1.9 km of Annapolis Harbor and 48 km of Sports Legends Museum At Camden Yards, Inn on Main Annapolis offers rooms with air conditioning and a private bathroom in Annapolis.
Entire Private 2 bedrooms house, nice neighborhood
Boasting a hot tub, Entire Private 2 bedrooms house, nice neighborhood is located in Arnold.
Welcome to our newly built house
Offering garden views, Welcome to our newly built house is an accommodation set in Glen Burnie, 19 km from Pier Six Concert Pavilion and 19 km from Harbor East Marina.
The Ultimate cozy escape
The Ultimate cozy escape is situated in Glen Burnie, 19 km from Sports Legends Museum At Camden Yards, 19 km from Baltimore Convention Center, and 20 km from Inner Harbor.
Annapolis Vacation Home 2 Mi to Quiet Waters Park
Situated in Annapolis, 5.2 km from Annapolis Harbor and 44 km from Addison Road-Seat Pleasant, Annapolis Vacation Home 2 Mi to Quiet Waters Park offers air conditioning.
Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!
Boasting lake views, Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! features accommodation with a garden and a patio, around 14 km from Annapolis Harbor.
Private Single Family Home Close to Both Water and Downtown!
Featuring air-conditioned accommodation with a patio, Private Single Family Home Close to Both Water and Downtown! is located in Annapolis.
Waterfront Annapolis Home Fire Pit and Fishing Pier
Located in Annapolis, 14 km from Annapolis Harbor and 46 km from Sports Legends Museum At Camden Yards, Waterfront Annapolis Home Fire Pit and Fishing Pier offers air conditioning.
Chase Creek Retreat
Situated in Annapolis, 13 km from Annapolis Harbor and 38 km from Sports Legends Museum At Camden Yards, Chase Creek Retreat features a restaurant.
Top picks for Annapolis hotels
Explore our most popular hotels in Annapolis
- Scored out of 10, guest rating 8.2Very good - What previous guests thought, 301 reviewsFromUS$1651 night, 2 adults
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 53 reviewsFromUS$1381 night, 2 adults
- Scored out of 10, guest rating 8.8Fabulous - What previous guests thought, 16 reviewsFromUS$1151 night, 2 adults
- Scored out of 10, guest rating 9.2Superb - What previous guests thought, 16 reviewsFromUS$2851 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 8 reviewsFromUS$3091 night, 2 adults
- Scored out of 10, guest rating 8.4Very good - What previous guests thought, 17 reviewsFromUS$3221 night, 2 adults
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Gaia House
Featuring air-conditioned accommodation with a patio, Gaia House is located in Annapolis. This property offers access to a balcony, free private parking and free WiFi.
Inn on Main Annapolis
Set within 1.9 km of Annapolis Harbor and 48 km of Sports Legends Museum At Camden Yards, Inn on Main Annapolis offers rooms with air conditioning and a private bathroom in Annapolis.
Entire Private 2 bedrooms house, nice neighborhood
Boasting a hot tub, Entire Private 2 bedrooms house, nice neighborhood is located in Arnold.
Welcome to our newly built house
Offering garden views, Welcome to our newly built house is an accommodation set in Glen Burnie, 19 km from Pier Six Concert Pavilion and 19 km from Harbor East Marina.
The Ultimate cozy escape
The Ultimate cozy escape is situated in Glen Burnie, 19 km from Sports Legends Museum At Camden Yards, 19 km from Baltimore Convention Center, and 20 km from Inner Harbor.
Annapolis Vacation Home 2 Mi to Quiet Waters Park
Situated in Annapolis, 5.2 km from Annapolis Harbor and 44 km from Addison Road-Seat Pleasant, Annapolis Vacation Home 2 Mi to Quiet Waters Park offers air conditioning.
Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!
Boasting lake views, Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! features accommodation with a garden and a patio, around 14 km from Annapolis Harbor.
Private Single Family Home Close to Both Water and Downtown!
Featuring air-conditioned accommodation with a patio, Private Single Family Home Close to Both Water and Downtown! is located in Annapolis.
Waterfront Annapolis Home Fire Pit and Fishing Pier
Located in Annapolis, 14 km from Annapolis Harbor and 46 km from Sports Legends Museum At Camden Yards, Waterfront Annapolis Home Fire Pit and Fishing Pier offers air conditioning.
Chase Creek Retreat
Situated in Annapolis, 13 km from Annapolis Harbor and 38 km from Sports Legends Museum At Camden Yards, Chase Creek Retreat features a restaurant.
Most booked holiday rentals in Annapolis and surroundings in the past month
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Popular with guests booking holiday rentals in Annapolis
Highly rated holiday rentals in Annapolis and nearby
Entire Private 2 bedrooms house, nice neighborhood
Boasting a hot tub, Entire Private 2 bedrooms house, nice neighborhood is located in Arnold.
Searenity Stays
Set in Edgewater in the Maryland region and Triton Beach reachable within 700 metres, Searenity Stays offers accommodation with free WiFi, a children's playground, a private beach area and free...
These holiday rentals in Annapolis and nearby have options with free cancellation
The Little House
Boasting air-conditioned accommodation with a patio, The Little House is set in Annapolis.
* Midcentury Modern Getaway * Prime Location *
Set in Annapolis, 2 km from Annapolis Harbor and 48 km from Sports Legends Museum At Camden Yards, * Midcentury Modern Getaway * Prime Location * offers air-conditioned accommodation with a balcony...
Anchors Aweigh
Featuring air-conditioned accommodation with a patio, Anchors Aweigh is set in Annapolis.
Seas The Bay
Boasting air-conditioned accommodation with a patio, Seas The Bay is situated in Annapolis.
The Master Shipwright
Boasting air-conditioned accommodation with a balcony, The Master Shipwright is situated in Annapolis. Guests staying at this holiday home have access to a patio.
Harrison Hall
Boasting air-conditioned accommodation with a patio, Harrison Hall is set in Annapolis.
Annapolis 3BR, Minutes to US Naval Academy & Dock
Annapolis 3BR, Minutes to US Naval Academy & Dock, a property with a garden, is set in Annapolis, 40 km from Addison Road-Seat Pleasant, 46 km from Sports Legends Museum At Camden Yards, as well as 47...
The Admiral's Retreat
Boasting air-conditioned accommodation with a private pool, pool view and a balcony, The Admiral's Retreat is situated in Annapolis. This holiday home features accommodation with a patio.
Enjoy breakfast in Annapolis and nearby
Base Camp on the Lake
Located in Annapolis, 1.6 km from Bay Ridge Beach and 7.2 km from Annapolis Harbor, Base Camp on the Lake offers air conditioning. A hot tub is available for guests.
Annapolis Bay Ridge Retreat
Located in Annapolis, 1.6 km from Bay Ridge Beach and 7.2 km from Annapolis Harbor, Annapolis Bay Ridge Retreat offers air conditioning.
The Ship's Bridge
Boasting air-conditioned accommodation with a balcony, The Ship's Bridge is situated in Annapolis. This beachfront property offers access to a terrace.
Bella Chateau
Boasting air-conditioned accommodation with a patio, Bella Chateau is situated in Annapolis.
The Salty Crab
Situated in Annapolis, less than 1 km from Bay Ridge Beach and 7.1 km from Annapolis Harbor, The Salty Crab offers air conditioning. This beachfront property offers access to a patio.
Thomas Point Tranquility
Boasting air-conditioned accommodation with a private pool, Thomas Point Tranquility is set in Annapolis. This holiday home offers accommodation with a patio.
Coastal Edgewater Home with Private Hot Tub!
Located in Annapolis, 20 km from Annapolis Harbor and 36 km from Addison Road-Seat Pleasant, Coastal Edgewater Home with Private Hot Tub! offers air conditioning.
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