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Annapolis, MD vacation rentals
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Best Vacation rentals and Airbnb offers in Annapolis, MD

Best Annapolis, MD vacation rentals with a balcony

Walk To The Naval Academy And Historic Annapolis.  Private Parking At The Home. - Annapolis, MD
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.
New! Private, Family-friendly Home Near Usna - Annapolis, MD
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.

Historic Row Home | Hot Tub - 1 Block From Gate 1! - Annapolis, MD
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.
Victory House
4br At Stadium•minutes To Usna & Dta - Annapolis, MD
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.
Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4 - Annapolis, MD
10 12 reviews
Annapolis, MD
07/16 – 07/19
$412/nighttotal: $1236 (3 )

Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4

2 4
apartment , Annapolis
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?

    Step Out To Main Street From A Chic Loft, Modern Apartment Over The Heart Of Main Street and Brand New Reno In Historic Dist W 2 Parking Spots are the most popular Airbnb and vacation rentals in Annapolis, MD among travelers.

  • 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

Downtown Gem! Stay In A Historic Carriage House Steps From Main Street, City Dock & Usna - Annapolis, MD
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.
Upscale Family Retreat Near Downtown Annapolis | Resort-style Outdoor Spaces - Annapolis, MD
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.

Captains Quarters | Waterfront & Pool - Annapolis, MD
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.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
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.

Five Star Charmer! Great Location Downtown & Stadium! Parking Too! - Annapolis, MD
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
This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape. - Annapolis, MD
Annapolis, MD
07/01 – 07/08
$1953/nighttotal: $13671 (7 )

This Thoughtfully Styled Home Overlooks The Bay And Is Perfect For Your Annapolis Escape.

5 2
apartment , Annapolis
Sailboat Experience In Annapolis - Annapolis, MD
9.9 55 reviews
Annapolis, MD
06/27 – 06/29
$275/nighttotal: $550 (2 )

Sailboat Experience In Annapolis

1 2
boat , Annapolis
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