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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

Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown - Annapolis, MD
10 1 review

Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown

apartment, Annapolis
This newly built vacation rental in Annapolis's Bestgate area is located 3 miles from the United States Naval Academy, 2 miles from Navy-Marine Corps Memorial Stadium, and 3 miles from the Annapolis Historic District, with Anne Arundel Medical Center 1 mile away.
This spacious 3000 square foot house offers 4 bedrooms, 4 bathrooms, and accommodates up to 9 guests, featuring a unique rooftop bedroom with a wet bar and patio, a full kitchen, air conditioning, terrace, parking with an EV charger, and is pet-friendly.
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
10 20 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis
This smoke-free Annapolis vacation home is located in the Historic District, a 15-minute walk from the U.S. Naval Academy and Maynard-Burgess House, and under 5 minutes from the Maryland Federation of Art and Ellen O. Moyer Nature Park. This 12,640-square-foot property boasts three bedrooms, two bathrooms, sleeps nine guests, and features a fully equipped kitchen, fenced yard with barbecue grills, and free Wi-Fi.
Spectacular Location: State Circle Apartment - Annapolis, MD
10 18 reviews

Spectacular Location: State Circle Apartment

apartment, Annapolis
This Annapolis apartment is located in the Historic District, just a short walk from the Thurgood Marshall Memorial, the U.S. Naval Academy, and the lively 97, 99, and 101 East Street area. The apartment consistently receives excellent user ratings, making it a popular choice for travelers.
The 800 square foot apartment comfortably accommodates up to 7 guests with two bedrooms and two bathrooms. Guests can enjoy convenient amenities such as a full kitchen, a washing machine, a sofa bed, and a TV, perfect for a relaxing stay in Annapolis.
Acrross From Usna Gate 3 W Patio At Hanover House - Annapolis, MD
9.9 75 reviews

Acrross From Usna Gate 3 W Patio At Hanover House

apartment, Annapolis
This Annapolis vacation home is located in the Historic District, within walking distance of St. John's College, Chase Lloyd House, and Hammond-Harwood House. The U.S. Naval Academy and French Soldiers Monument are also a short walk away. The property has excellent user, location, and cleanliness ratings.
This 1950 square foot house has four bedrooms and can accommodate eight guests. It includes a fully equipped kitchen, a fireplace, a balcony, a garden, a spa, parking, and a gas grill.

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.

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard - Annapolis, MD
10 22 reviews

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard

apartment, Annapolis
This Annapolis vacation rental, located in the Admiral Heights neighborhood, is 0.7 miles from the Navy-Marine Corps Memorial Stadium and 2 miles from both downtown Annapolis and the U.S. Naval Academy.
This four-bedroom, two-bathroom home sleeps nine guests and features a private backyard with a fire pit, a fully equipped kitchen with stainless steel appliances, high-speed WiFi, Smart TVs, and driveway parking; nearby attractions include the Smithsonian Environmental Research Center and Peters Cove.
Brand New. 1.5 Blocks To Westin.1st Floor Bed/bath - Annapolis, MD
10 130 reviews

Brand New. 1.5 Blocks To Westin.1st Floor Bed/bath

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.
Annapolis Charm 3br Downtown - Annapolis, MD
10 1 review

Annapolis Charm 3br Downtown

house, Annapolis
This 3-bedroom home in Downtown Annapolis is 2.2 miles from Annapolis Harbor and 20 miles from Baltimore - Washington International Airport.
This family-friendly rental offers free on-site parking, complimentary WiFi, air conditioning, and a garden, accommodating up to 13 guests.
Historic Row Home In Downtown Annapolis - Annapolis, MD
No reviews

Historic Row Home In Downtown Annapolis

apartment, Annapolis
This two-story Annapolis apartment rental is located in the Historic District, steps from the U.S. Naval Academy, St. John's College, and City Dock.
The 1100-square-foot residence features two bedrooms, two bathrooms, a private patio, and sleeps up to eight guests, with amenities including a full kitchen, in-unit laundry, and convenient proximity to restaurants and shops.

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

Annapolis Home | Fenced Yard | Pool Table | 10 Gue - Annapolis, MD
9.8 41 reviews

Annapolis Home | Fenced Yard | Pool Table | 10 Gue

apartment, Arnold
This Arnold home is conveniently located just a short drive from downtown Annapolis, the US Naval Academy, and the US Naval Stadium, offering easy access to a range of attractions.
The 3-bedroom, 2-bathroom house features two family rooms, a fully equipped kitchen, a bumper pool table, and a garden, comfortably accommodating up to 10 guests.
Walk To Waterfront Eastport Backyard & Fire Pit - Annapolis, MD
9.6 63 reviews

Walk To Waterfront Eastport Backyard & Fire Pit

apartment, Annapolis
This Annapolis vacation home is located in Eastport, a short walk from both the Annapolis Maritime Museum and the U.S. Naval Academy, offering easy access to these popular destinations. The property has received excellent ratings for user experience, location, and cleanliness.
The 2-bedroom house, with a total floor area of 850 square feet, comfortably sleeps up to 7 guests. Amenities include a fully equipped kitchen, a spacious garden, a terrace, a barbecue grill, and free WiFi, making it ideal for families and groups looking for a relaxing and enjoyable stay.
Charming City Oasis. Walk To Harbor, Eateries.usna - Annapolis, MD
9.7 116 reviews

Charming City Oasis. Walk To Harbor, Eateries.usna

apartment, Annapolis
This charming cottage is located in a peaceful residential neighborhood just a short walk from Annapolis's vibrant harbor, shops, and restaurants. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The cottage comfortably accommodates up to six guests with multiple sleeping areas, including a master bedroom and a nautical-themed room. Enjoy modern amenities like smart TVs, Wi-Fi, and a Keurig coffee maker, along with outdoor activities like cornhole and a private patio with a fire pit.
Coastal Edgewater Home W/ Private Hot Tub! - Annapolis, MD
9.2 50 reviews

Coastal Edgewater Home W/ Private Hot Tub!

apartment, Mayo
This 5-bedroom vacation rental is located in Edgewater, just a short drive from Mayo Beach Park and Holiday Hill Marina. The apartment consistently receives excellent ratings for cleanliness, location, and overall experience.
The spacious home comfortably accommodates up to 9 guests and offers modern amenities like central air conditioning, a fully equipped kitchen, and a private hot tub. Enjoy outdoor entertainment with a furnished deck, gas grill, fire pit, and cornhole, or relax with board games and a wine cooler.

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.

Oasis By The Bay - Waterfront Heated Pool Hot Tub! - Annapolis, MD
8.8 6 reviews

Oasis By The Bay - Waterfront Heated Pool Hot Tub!

apartment, Highland Beach
This six-bedroom, six-bathroom waterfront home in Highland Beach, Maryland, is located on a Severn River inlet, five miles from Annapolis and a 15-20 minute drive from the US Naval Academy.
The 5,600-square-foot residence boasts a private heated pool, hot tub, spacious interior with fireplace and wet bar, in-law suite, and ample parking for up to four vehicles, accommodating up to 18 guests and offering Chesapeake Bay views.
Private Art-filled Guesthouse Near Naval Academy - Annapolis, MD
10 171 reviews

Private Art-filled Guesthouse Near Naval Academy

house, Annapolis
This charming guesthouse is located in the West Annapolis residential neighborhood, where you can explore quaint shops and restaurants nearby. It has excellent user, location, and cleanliness ratings.
The secluded guesthouse has a unique blend of antique curios and Americana decor, a modern kitchen, and an updated bathroom. It can accommodate up to 2 guests and offers a Treetop Getaway experience with key code access for convenience. The homeowners are on-site for assistance. You will enjoy amenities such as a swimming pool, parking, air conditioning, and internet.
The Retreat @ Back Creek - Annapolis, MD
9.9 41 reviews

The Retreat @ Back Creek

apartment, Annapolis
This waterfront home in Eastport is within walking distance of downtown Annapolis. It has excellent user, location, and cleanliness ratings.
The five-level home has five bedrooms and three bathrooms and can accommodate up to 16 guests. It features an indoor heated pool, a gourmet kitchen, an expansive great room with a fireplace, an entertainment room, a rec room with a bar and ping pong table, an indoor pool room with a hot tub and sauna, and a landscaped private patio with a fire pit and grill.
Modern Eastport Getaway, Near Historic Annapolis - Annapolis, MD
9.7 19 reviews

Modern Eastport Getaway, Near Historic Annapolis

apartment, Annapolis
This Annapolis apartment rental is centrally located, offering easy access to Annapolis's downtown area and the waterfront.
The one-bedroom, one-bathroom unit sleeps four guests and includes a kitchen, air conditioning, swimming pool access, and 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.

Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View - Annapolis, MD
9.8 29 reviews

Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View

apartment, Highland Beach
Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen - Annapolis, MD
9.0 12 reviews

Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen

apartment, Crownsville
Quiet Woodland Lodge W Community Beach Access & Large Private Deck - Annapolis, MD
No reviews

Quiet Woodland Lodge W Community Beach Access & Large Private Deck

apartment, Annapolis
Beautiful Waterfront Home On The Chesapeake Bay With Private Dock & Beach Access - Annapolis, MD
No reviews

Beautiful Waterfront Home On The Chesapeake Bay With Private Dock & Beach Access

apartment, Highland Beach

Discover 5-Star Vacation Rentals in Annapolis, MD

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

Beautiful Historic Home Next To City Dock + Usna - Annapolis, MD
10 52 reviews

Beautiful Historic Home Next To City Dock + Usna

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 Basement Apartment In An Upscale Home - Annapolis, MD
9.8 8 reviews

Beautiful Basement Apartment In An Upscale Home

apartment, Arnold
Oasis By The Bay - Waterfront Heated Pool Hot Tub - Annapolis, MD
10 3 reviews

Oasis By The Bay - Waterfront Heated Pool Hot Tub

house, Highland Beach
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