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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

Historic Row Home | Hot Tub - 1 Block From Gate 1! - Annapolis, MD
9.0 10 reviews

Historic Row Home | Hot Tub - 1 Block From Gate 1!

apartment, Annapolis
This Annapolis vacation rental is located in the Historic District, a short walk from City Dock and near attractions like Jonas Green State Park and the Hammond-Harwood House.
This 2,000-square-foot home features three bedrooms, two bathrooms, a fully equipped kitchen, in-unit laundry, a private balcony, and access to a grilling area and garden, comfortably accommodating families.
Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.8 11 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This Annapolis townhouse, centrally located near Navy Stadium and two miles from the United States Naval Academy, offers easy access to major attractions.
The 3,190-square-foot property boasts a spacious layout sleeping up to 10 guests, featuring a chef's kitchen with GE Café appliances, a finished basement, and proximity to Heineman Park, Harts Cove, and a community pool.
Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & Parking

apartment, Annapolis
This three-bedroom, two-bathroom Annapolis condo is located in Eastport, less than a mile from Spa Creek and the U.S. Naval Academy, and within a 15-minute drive of the Kunta Kinte-Alex Haley Memorial.
The 7-guest unit features a fully equipped kitchen, in-unit laundry, free WiFi, a balcony, a swimming pool, secure parking, and elevator access, offering easy access to Annapolis attractions.
Secluded Cozy Cottage In Historic Downtown - Annapolis, MD
9.6 22 reviews

Secluded Cozy Cottage In Historic Downtown

cottage, Annapolis
This charming cottage, in the Historic District of Annapolis, offers immediate access to the city's iconic landmarks and attractions. The restored 1930s cottage has an open and airy interior with vaulted ceilings and an open floor plan.
The cottage has 2 bedrooms, 1 bathroom, and can accommodate up to 8 guests. It features a fully equipped gourmet kitchen, a comfortable living area with a large couch, chaise lounge chairs, a 55" Roku TV, and an electric fireplace. The cottage also has a private entrance and patio, and is pet-friendly.

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.

Downtown Annapolis King George 3rd Floor Hideaway - Annapolis, MD
9.8 153 reviews

Downtown Annapolis King George 3rd Floor Hideaway

apartment, Annapolis
This apartment is located in Downtown Annapolis, just a short walk from the Annapolis Harbor and 30 miles from Baltimore. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features one bedroom and one bathroom, offering 700 square feet of living space. You'll enjoy a fully equipped kitchen, a private terrace, and a garden with barbecue facilities, perfect for relaxing after a day exploring Annapolis.
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.9 77 reviews

Cute Bungalow Blocks To Stadium

apartment, Annapolis
This stylish two-bedroom house is located in Annapolis' Germantown neighborhood, just two blocks from Navy-Marine Corps Memorial Stadium and an 8-minute drive from the USNA and Downtown Annapolis. The home has received excellent ratings for location, cleanliness, and overall user experience.
The house is a two-floor home with a capacity of 6 guests. This Annapolis home offers amenities like a fully equipped kitchen, air conditioning, a fenced-in backyard, and a covered, screened-in eating area.
Dog Friendly! Next To Navy Stadium And Dta Shuttle! - Annapolis, MD
10 12 reviews

Dog Friendly! Next To Navy Stadium And Dta Shuttle!

apartment, Annapolis
This Annapolis vacation rental is conveniently located within one mile of the U.S. Naval Academy and the Navy-Marine Corps Memorial Stadium, offering easy access to Helen Avalynne Tawes Garden and Peters Cove within a 10-minute drive.
This 1,190-square-foot house features two bedrooms, one bathroom, and accommodates up to six guests, boasting a fully equipped kitchen, private patio, free Wi-Fi, and a smoke-free environment.
Perfect Eastport Location - Annapolis, MD
10 147 reviews

Perfect Eastport Location

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.

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.

Popular destinations

Best Annapolis, MD vacation rentals with parking

Pet Friendly | Park Free & Walk To Usna Stadium - Annapolis, MD
10 66 reviews

Pet Friendly | Park Free & Walk To Usna Stadium

apartment, Annapolis
This 4-bedroom house is located in West Annapolis, just a short walk from the Navy-Marine Corps Stadium and a variety of restaurants, shops, and the new RAR Brewery. This accommodation has excellent user, location, and cleanliness ratings.
The house has two bathrooms and can accommodate up to 10 guests. Amenities include a private bar and gym in the garage, a fenced-in backyard, a full kitchen, and Apple TV.
Large Priv. Suite Near D-town Annapolis & Stadium - Annapolis, MD
9.9 32 reviews

Large Priv. Suite Near D-town Annapolis & Stadium

apartment, Annapolis
This Annapolis guesthouse is centrally located, minutes from the U.S. Naval Academy, downtown Annapolis, Annapolis Town Center, and Route 50, with easy walking access to Navy-Marine Corps Memorial Stadium.
The spacious one-bedroom suite features a private entrance, bathroom, large sitting/TV area, eating area, fridge, microwave, coffee maker, milk frother, and accommodates two guests; potential access to an outdoor patio with dining and grilling facilities is available.
Spacious 5 Br House - 5 Min Walk To N-mc Stadium - Annapolis, MD
9.5 2 reviews

Spacious 5 Br House - 5 Min Walk To N-mc Stadium

house, Annapolis
This Annapolis home is a five-minute walk from the Navy-Marine Corps Stadium and 2.6 miles from Annapolis Harbor, offering easy access to both sporting events and waterfront activities.
This 2600-square-foot residence boasts five bedrooms, four bathrooms, and accommodates up to 16 guests, featuring a fully equipped kitchen, air conditioning, free Wi-Fi, and a private garden.
Circa 1885-historic Annapolis-usna Gate 1 - Annapolis, MD
10 198 reviews

Circa 1885-historic Annapolis-usna Gate 1

apartment, Annapolis
This charming Annapolis apartment is located in the historic district, just a two-block walk from the downtown area, making it easy to explore the city's attractions, restaurants, and shops. It has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment features two bedrooms, a family room with a pull-out sofa, and a full eat-in kitchen, comfortably accommodating up to five guests. Amenities include keyless entry, in-unit laundry, a fully equipped kitchen, and a bathroom with an antique clawfoot tub, offering a unique blend of modern convenience and historic charm.

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.

Waterfront Suite With Views Of Annapolis From Prime Eastport Location - Annapolis, MD
10 5 reviews

Waterfront Suite With Views Of Annapolis From Prime Eastport Location

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.
Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 15 reviews

Waterfront 2-bedroom Condo On Spa Creek

apartment, Annapolis
This two-bedroom Annapolis condo is conveniently located in Eastport, less than a mile from Spa Creek and the U.S. Naval Academy, and within a 10-minute drive of Annapolis Harbor and the Kunta Kinte-Alex Haley Memorial.
The unit offers a fully equipped kitchen, private patio, free WiFi, access to a swimming pool, fitness center, and spa, comfortably accommodating up to six guests.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 30 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This smoke-free Annapolis vacation home is located in the Murray Hill neighborhood, less than a mile from the U.S. Naval Academy and the Annapolis Civil Rights Plaque.
This 3,300-square-foot house features seven bedrooms, four bathrooms, and can comfortably accommodate fourteen guests, boasting amenities such as a fully equipped kitchen, fireplace, garden, and barbecue grills.
Waterfront Oasis Of Annapolis Star - Annapolis, MD
10 87 reviews

Waterfront Oasis Of Annapolis Star

apartment, Arnold
This Arnold apartment is conveniently located within 3 miles of Maryland World War II Memorial, Jonas Green State Park, and Naval Health Clinic, offering easy access to local attractions. Guests consistently rate this rental "excellent," making it a popular choice for travelers.
The apartment is family-friendly and pet-friendly, featuring a private pool, fireplace, fully equipped kitchen, and modern amenities like a microwave, coffee/tea maker, free WiFi, and a Smart TV. Enjoy the convenience of air conditioning, a terrace or balcony, a garden, and parking, as well as the relaxation of the swimming pool and water park.

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.

Spacious 5-bedroom House With Ac In Gorgeous Annapolis Historic District Capital - Annapolis, MD
No reviews

Spacious 5-bedroom House With Ac In Gorgeous Annapolis Historic District Capital

apartment, Annapolis
Cozy 3br Annapolis Sleeps 6 Private Deck, Parking - Annapolis, MD
No reviews

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking

house, Annapolis
Serene Sunsets At Historic Waterfront Home - Annapolis, MD
9.6 34 reviews

Serene Sunsets At Historic Waterfront Home

apartment, Mayo
Luxe Row Home Steps To Usna Gate 3! - Annapolis, MD
10 23 reviews

Luxe Row Home Steps To Usna Gate 3!

house, Naval Academy

Discover 5-Star Vacation Rentals in Annapolis, MD

Experience 5-star comfort in a luxury Annapolis, MD vacation rental designed with premium amenities throughout.

Downtown Furnished Apartment - Walking Distance To Restaurants - Annapolis, MD
10 11 reviews

Downtown Furnished Apartment - Walking Distance To Restaurants

apartment, Annapolis

Best Vacation Rentals with a Steam Room in Annapolis, MD

Recover properly with on-site sauna access, a standard feature at these premier Annapolis, MD vacation rentals.

Beautiful 6br Home In Annapolis - Annapolis, MD
9.3 68 reviews

Beautiful 6br Home In Annapolis

apartment, Annapolis
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