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Best Vacation rentals and Airbnb offers in Annapolis, MD
10 49 reviews
Annapolis, MD
07/01 – 07/08
$512/nighttotal: $3584 (7 )
New Year Deal! K&q Beds+kit For Price 1 Hotel Room
1 2
apartment , Annapolis
This downtown Annapolis rental is a two-minute walk from Main Street, six minutes from the U.S. Naval Academy, and five minutes from Annapolis Harbor, offering easy access to historic sites and attractions. The two-bedroom, two-bathroom apartment sleeps six guests and features a fully equipped chef's kitchen with Williams Sonoma appliances, a private patio with a gas firepit, Helix Lux mattresses, high-speed Wi-Fi, and keyless entry.
10 5 reviews
Annapolis, MD
06/19 – 06/21
$715/nighttotal: $1430 (2 )
Steps To Usna Gate 1 And Main St On King George St
1 2
apartment , Annapolis
This newly renovated apartment in Historic Annapolis is located on King George Street, just 2 blocks from the U.S. Naval Academy Gate 1 and a short walk to the waterfront. This 3-bedroom, 1-bathroom rental accommodates up to 6 guests and features a gourmet kitchen, a private fenced patio with a grill and firepit, WiFi, and in-home laundry, offering easy access to restaurants and boutiques, with Washington, DC 30 miles away and Baltimore 25 miles away.
9.8 112 reviews
Annapolis, MD
07/16 – 07/19
$648/nighttotal: $1944 (3 )
Walk To Usna, Main St W Parking Historic Wisteria
3 5
apartment , Annapolis
This Annapolis vacation home is located in the Historic District, just a short walk from The Colonial Players and the U.S. Naval Academy, offering easy access to the city's rich history and culture. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The house has four bedrooms and can accommodate up to eight guests, providing ample space for families or groups of friends. Amenities include a fully equipped kitchen, free WiFi, a terrace, a garden, a spa, and parking, making it perfect for a relaxing and enjoyable vacation.
Annapolis, MD
08/06 – 08/10
$1450/nighttotal: $5800 (4 )
Annapolis Gem- Tranquil 4 Br Murray Hill Victorian
1 10
house , Annapolis
This Murray Hill Victorian house in Annapolis is located 1.7 miles from Annapolis Harbor and approximately 25-26 miles from Baltimore landmarks such as the Inner Harbor and Baltimore Convention Center. This 1910 square foot residence accommodates up to 15 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen with a dishwasher, air conditioning, WiFi, and a private patio.
10 1 review
Annapolis, MD
07/12 – 07/13
$845/nightfor 1 night
Eastport 3 Bedroom Cottage: Walk To Downtown
3 2
apartment , Annapolis
This updated Eastport cottage is located in a historic neighborhood known for its marinas, waterfront dining, and local shops, and is a 15-minute walk to Downtown Annapolis and Annapolis Harbor. This residence offers 3 bedrooms, 2 bathrooms, and comfortably sleeps 8 guests with a fully equipped kitchen, a spacious backyard, and two living areas, providing convenient self-check-in for your stay.
Annapolis, MD
08/06 – 08/10
$1250/nighttotal: $5000 (4 )
All Tucked Inn
1 10
house , Annapolis
All Tucked Inn, an Annapolis house rental, is conveniently located 2.5 miles from Annapolis Harbor and 30 miles from Baltimore attractions including Camden Yards and the Inner Harbor. This one-bedroom, three-bathroom property sleeps 15 guests and features free Wi-Fi, parking, a full kitchen with dishwasher, and air conditioning.
9.8 352 reviews
Annapolis, MD
01/01 – 02/01
$118/nighttotal: $3658 (31 )
Private Annapolis Inlaw Apartment
1 2
apartment , Annapolis
This Annapolis apartment is located in a quiet neighborhood just a short distance from the bustling downtown area, offering easy access to shops, restaurants, and historic attractions. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The apartment features a comfortable king-size bed, two queen-size blow-up beds, and a large sectional sofa, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, parking, and internet access for your convenience.
9.5 34 reviews
Annapolis, MD
07/24 – 07/27
$237/nighttotal: $711 (3 )
Downtown Apartment With Parking!
1 2
apartment , Annapolis
This Annapolis apartment rental is ideally located in the historic district, steps from the U.S. Naval Academy and a short walk from downtown's shops and restaurants. The one-bedroom, one-bathroom unit sleeps four, featuring a fully equipped kitchen with a Nespresso machine, a 55" smart TV, and keypad entry; parking is included, a rare amenity in this area.
9.8 12 reviews
Annapolis, MD
09/25 – 10/18
$460/nighttotal: $10580 (23 )
Weems Creek Cottage, Annapolis Waterfront
1 2
house , Annapolis
Weems Creek Cottage is a charming waterfront vacation rental located just 2.7 miles from Annapolis Harbor, offering stunning views of the Chesapeake Bay. The cottage is conveniently situated near the city's vibrant waterfront scene, making it easy to explore Annapolis's historic attractions and bustling harbor. This cozy cottage provides 700 square feet of space, perfect for accommodating up to 7 guests. The cottage features a fully equipped kitchen, a private spa, and free Wi-Fi, ensuring a comfortable and relaxing stay.
10 128 reviews
Annapolis, MD
12/03 – 12/06
$750/nighttotal: $2250 (3 )
Brand New.1.5 Blocks To Westin. 1st Floor Bed & Bath. Walkable Convenience
1 10
apartment , Annapolis
This four-bedroom, three-bathroom Annapolis home is located in the Homewood neighborhood, just a short walk from the Westin Hotel and half a mile from the stadium. The 2,590-square-foot apartment comfortably sleeps 10 guests and features modern design, a gourmet kitchen with high-end appliances, a garden, a spa, and off-street parking.
9.7 135 reviews
Annapolis, MD
06/30 – 07/03
$217/nighttotal: $651 (3 )
Anchor's Away In The Heart Of Eastport!
1 2
apartment , Annapolis
This Annapolis apartment is located in the Eastport district, within walking distance of the Annapolis Maritime Museum and U.S. Naval Academy. It has excellent user, location, and cleanliness ratings. The apartment has one bedroom and one bathroom, and it features a fully equipped kitchen, a smart TV, free WiFi, and a terrace or balcony. Guests can also enjoy access to barbecue grills, laundry facilities, and a smoke-free environment.
10 138 reviews
Annapolis, MD
06/27 – 06/29
$385/nighttotal: $770 (2 )
Perfect Eastport Location, Walk Everywhere
1 2
apartment , Annapolis
This apartment is ideally situated in the heart of Eastport, a charming waterfront neighborhood within walking distance of downtown Annapolis (less than a mile) with excellent user, location and cleanliness ratings. The interior design reflects the maritime heritage of the area, and the apartment is fully equipped with a kitchen, washer and dryer, free Wi-Fi, and a Smart TV. The apartment is suitable for regatta attendees and visitors to Annapolis.
Best Annapolis, MD vacation rentals with a balcony
10 45 reviews
Annapolis, MD
08/21 – 08/24
$867/nighttotal: $2601 (3 )
Walk To The Naval Academy And Historic Annapolis. Private Parking At The Home.
3 2
apartment , Annapolis
This Annapolis Historic District row house rental is located five houses from Ego Alley, a four-minute walk from the U.S. Naval Academy, and one block from Main Street, offering easy access to shops and restaurants. The three-bedroom, three-bathroom apartment sleeps six guests and features a full kitchen with dishwasher, in-unit laundry, a terrace, and dedicated parking—a rare find in Annapolis.
Annapolis, MD
07/16 – 07/19
$643/nighttotal: $1929 (3 )
New! Private, Family-friendly Home Near Usna
3 5
house , Annapolis
This family-friendly house in Annapolis is located 3.2 miles from Annapolis Harbor and 24 miles from Addison Road-Seat Pleasant. This 1190 sq ft home features 3 bedrooms, 2 bathrooms, and can accommodate up to 13 guests, offering amenities like a full kitchen, air conditioning, a garden, a patio, and private parking.
Guest-Favorite Family Vacation Rentals in Annapolis, MD
These family-friendly vacation rentals in Annapolis, MD offer spacious layouts and easy access to local beaches.
10 24 reviews
Annapolis, MD
07/01 – 07/08
$542/nighttotal: $3794 (7 )
Historic Row Home | Hot Tub - 1 Block From Gate 1!
3 2
apartment , Annapolis
This Annapolis yacht rental is steps from the US Naval Academy's Gate 1, St. John's College, and City Dock, offering easy access to Annapolis's historic district and attractions. This three-story vessel sleeps nine guests comfortably in three bedrooms and features a chef's kitchen with granite countertops, a dishwasher, and a microwave, plus a garden and air conditioning.
10 6 reviews
Annapolis, MD
12/03 – 12/06
$519/nighttotal: $1557 (3 )
Victory House
4br At Stadium•minutes To Usna & Dta
1 10
apartment , Annapolis
This Annapolis rental home in Admiral Heights is situated directly across from Navy-Marine Corps Memorial Stadium, a 5-minute drive to U.S. Naval Academy Gate 8, and an 8-minute drive to downtown Annapolis. This spacious 4-bedroom, 3-bathroom residence accommodates up to 10 guests and features a fully equipped kitchen, an open-concept living and dining area, and an outdoor firepit, with grocery stores and shopping just a 3-minute drive or 10-minute walk away.
This Annapolis waterfront home, near Brewer Hill, is a 10-minute walk from People's Brewer Hill Cemetery and Maryland Hall for Creative Arts, and 1.7 miles from the U.S. Naval Academy. This 750-square-foot vacation rental sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen, free Wi-Fi, a terrace, a garden, and a spa, plus on-site parking.
Frequently Asked Questions about vacation rentals in Annapolis, MD
Which neighborhood in Annapolis, MD should you consider for a vacation rental?
Downtown Annapolis is a great choice for a vacation rental, especially if you want to be close to the action. You can also consider the neighborhoods of Eastport or Spa Creek, which are a little quieter but still within walking distance of the downtown area.
What are the best Airbnb and vacation rentals in Annapolis, MD?
What are the top family-friendly attractions in Annapolis, MD?
The Maryland State House is a great place to learn about Annapolis history. The Annapolis Maritime Museum and Park is also a great option for families, with exhibits on the history of the Chesapeake Bay and a working boatyard. The Annapolis City Dock is a great place to watch the boats come and go, and there are often street performers and vendors there.
What are the most popular Airbnbs in Annapolis, MD?
When is the best time to book a vacation rental in Annapolis, MD?
The best time to book a vacation rental in Annapolis is during the shoulder seasons, which are spring and fall. The weather is still pleasant, but the crowds are smaller and the prices are lower. If you're looking for a more lively experience, you can visit during the summer, but be prepared for higher prices and larger crowds.
What are the best vacation rentals with a pool in Annapolis, MD?
What are the best budget-friendly activities in Annapolis, MD?
Walking around the historic downtown area is a great free activity. You can also visit the US Naval Academy Museum for free. The Annapolis City Dock is also a great place to people-watch and enjoy the views of the harbor.
What are the best rentals for families and kids in Annapolis, MD?
What are the best restaurants with local dishes in Annapolis, MD?
For a taste of local seafood, try the Annapolis Crab House or the Chart House. For a more casual dining experience, try the Blackwall Hitch or the Galway Bay Irish Pub. If you want to try something a little different, try the Pusser's Caribbean Grille.
What are the best rentals or Airbnbs with a jacuzzi in Annapolis, MD?
What are the best walking or cycling routes in Annapolis, MD?
The Annapolis Loop Trail is a great option for both walking and cycling. It's a 13-mile loop that takes you around the city and through some of the surrounding parks. The scenic route along the Chesapeake Bay is also a great option for a leisurely bike ride.
Are there pet-friendly attractions in Annapolis, MD?
Yes, many of the parks and walking trails in Annapolis are pet-friendly. The City Dock is also a popular spot for dog walkers. There are also a number of pet-friendly restaurants and shops in the downtown area.
What are the benefits of choosing a vacation rental in Annapolis, MD?
Vacation rentals offer more space and privacy than hotels. They also often come with amenities like kitchens and laundry facilities, which can be helpful for families or groups. Vacation rentals can also be a more affordable option than hotels, especially if you're traveling with a large group.
Destinations nearby
Best Annapolis, MD vacation rentals with parking
10 49 reviews
Annapolis, MD
09/25 – 10/18
$951/nighttotal: $21873 (23 )
Downtown Gem! Stay In A Historic Carriage House Steps From Main Street, City Dock & Usna
2 2
apartment , Annapolis
This restored 1857 row house is located in downtown Annapolis, just half a block from Main Street, two blocks from the waterfront, and three blocks from the United States Naval Academy. This 1,350 square foot house features two bedrooms with king and queen beds, a den with a sofa bed, and two full bathrooms, accommodating up to six guests, with a fully-equipped kitchen, private patio, and modern amenities like WiFi and keyless entry.
10 2 reviews
Annapolis, MD
06/19 – 06/21
$954/nighttotal: $1908 (2 )
Upscale Family Retreat Near Downtown Annapolis | Resort-style Outdoor Spaces
4 2
apartment , Annapolis
This family-friendly apartment in Annapolis is located a 3-minute drive from Navy-Marine Corps Memorial Stadium and a 5-minute drive from Thurgood Marshall Memorial. This 4-bedroom, 3-bathroom vacation rental accommodates up to 9 guests and features a garden, terrace with outdoor furniture, barbecue, fireplace, and in-unit laundry, with nearby ice skating and sailing activities.
Neighborhoods and points of interest in Annapolis, MD
Check Out Vacation Rentals with a Pool in Annapolis, MD
Enhance your coastal getaway with a Annapolis, MD vacation rental featuring a pool.
10 109 reviews
Annapolis, MD
08/21 – 08/24
$364/nighttotal: $1092 (3 )
Captains Quarters | Waterfront & Pool
1 2
apartment , Annapolis
This Annapolis yacht is located in the Eastport district, just a short walk from downtown Eastport restaurants and a short stroll over the Eastport Bridge to downtown Annapolis attractions. It's also close to the Naval Academy and downtown Annapolis. This yacht has received excellent ratings for location, cleanliness, and user experience. This two-bedroom, one-bathroom yacht comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, and free parking.
10 2 reviews
Annapolis, MD
07/16 – 07/19
$601/nighttotal: $1803 (3 )
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free
2 5
apartment , Annapolis
This Eastport condo provides waterfront living on Spa Creek with views, located 0.5 miles (2,640 feet) from downtown Annapolis and 0.8 miles (4,224 feet) from the U.S. Naval Academy. This residence accommodates up to 5 guests and features a private balcony, a seasonal swimming pool, high-speed WiFi, and assigned parking.
Browse Waterfront Vacation Rentals in Annapolis, MD
Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Annapolis, MD. Book your next shoreside stay today.
9.6 5 reviews
Annapolis, MD
07/16 – 07/19
$552/nighttotal: $1656 (3 )
Five Star Charmer! Great Location Downtown & Stadium! Parking Too!
2 4
apartment , Annapolis
Annapolis, MD
07/01 – 07/08
$1953/nighttotal: $13671 (7 )
This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape.