Compare Vacation Rentals & Airbnb in Annapolis, MD

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Annapolis, MD vacation rentals
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758 Rentals and Airbnb in Annapolis, MD

Best family friendly Annapolis, MD vacation rentals

Among the 758 accommodations in Annapolis, MD, here are the 4 best family friendly rentals

Beautiful Condo - Water View Near City Dock - Annapolis, MD
9.7 227 reviews
Annapolis, MD
11/09 – 19/09
$294/nighttotal: $2352 (8 )

Beautiful Condo - Water View Near City Dock

1 4
apartment , Annapolis
This one-bedroom apartment is conveniently located in Eastport, Annapolis, within walking distance of Spa Creek and the US Naval Academy. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The 57 square metre apartment comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private pool, access to a water park and outdoor pool, a fully equipped kitchen, a terrace, a garden, a spa, parking, and internet access.
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere. - Annapolis, MD
10 146 reviews
Annapolis, MD
01/01 – 01/02
$985/nighttotal: $30535 (31 )

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

3 2
apartment , Annapolis
This family-friendly house is located in the city centre of Annapolis, just under 2km from the Annapolis Civil Rights Plaque and the U.S. Naval Academy. The house has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The property spans 139 square metres and comfortably accommodates up to 10 guests across its three bedrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, a terrace, and free Wi-Fi.
Historic Suite 2 Blocks From Main St With On-site Parking | Dog-friendly - Annapolis, MD
10 12 reviews
Annapolis, MD
01/01 – 01/02
$610/nighttotal: $18910 (31 )

Historic Suite 2 Blocks From Main St With On-site Parking | Dog-friendly

2 2
apartment , Annapolis
This Annapolis apartment is situated in Historic Annapolis, a short walk (approximately 0.32 km) from Main Street and 0.64 km from the United States Naval Academy.
The two-bedroom, one-bathroom flat offers keyless entry, on-site parking, in-unit laundry, and sleeps six guests, boasting modern amenities including high-speed internet and a fully equipped kitchen with a dishwasher.
Elegant & Bright Historic Home 3br/2,5ba, 2 Kings, 1 Queen, 5 Min To Usna - Annapolis, MD
10 3 reviews
Annapolis, MD
01/01 – 01/02
$726/nighttotal: $22506 (31 )

Elegant & Bright Historic Home 3br/2,5ba, 2 Kings, 1 Queen, 5 Min To Usna

3 2
apartment , Annapolis
This 3-bedroom flat for 7 guests offers an unbeatable location in Annapolis's historic district, a mere 5-minute walk from the US Naval Academy and within 1 minute of the Maryland State House and Annapolis Town Dock.
This 125 square meter residence features a fully equipped kitchen with stainless-steel appliances, a lounge with a fireplace, two king-sized bedrooms, and three bathrooms, with free WiFi and air conditioning provided.

Best Annapolis, MD vacation rentals with a pool

Among the 758 accommodations in Annapolis, MD, here are the 4 best rentals with a pool

Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 12 reviews
Annapolis, MD
17/09 – 22/09
$850/nighttotal: $4250 (5 )

Waterfront 2-bedroom Condo On Spa Creek

2 1
apartment , Annapolis
This Annapolis Eastport apartment is less than 1.6km from Spa Creek and the United States Naval Academy, and within a 1.6km radius of Annapolis Harbour and the Kunta Kinte Plaque & Alex Haley Memorial.
This two-bedroom, one-bathroom property sleeps six, offering a fully equipped kitchen, private patio, free Wi-Fi, access to a swimming pool, spa, fitness centre, and parking; nearby attractions include the Naval Academy and Annapolis Harbour.
Prime Eastport Location - Waterfront Condo With Parking - Annapolis, MD
10 26 reviews
Annapolis, MD
27/06 – 29/06
$1116/nighttotal: $2232 (2 )

Prime Eastport Location - Waterfront Condo With Parking

2 2
apartment , Annapolis
This Annapolis apartment, situated in Eastport, is less than 2km from Spa Creek and the United States Naval Academy, offering easy access to the Kunta Kinte-Alex Haley Memorial and Maynard-Burgess House within a 15-minute drive.
The three-bedroom, two-bathroom property sleeps seven guests and includes a full kitchen, terrace, free Wi-Fi, on-site parking, and swimming pool access; nearby attractions include the Naval Academy and the Chesapeake Bay.
Entire Condo With Waterview, Pool & Parking - Annapolis, MD
10 8 reviews
Annapolis, MD
11/09 – 19/09
$716/nighttotal: $5728 (8 )

Entire Condo With Waterview, Pool & Parking

1 4
apartment , Annapolis
This recently refurbished Annapolis condo in Eastport is a 1.6km walk from Annapolis city centre and a 2.2km walk from the United States Naval Academy.
The two-bedroom, two-bathroom apartment sleeps four, boasts a king-size and queen-size bed, a private balcony, rooftop pool access (seasonal), and dedicated workspace with water views.
Spa Creek Waterfront | Pool & Parking - Annapolis, MD
10 7 reviews
Annapolis, MD
17/09 – 22/09
$600/nighttotal: $3000 (5 )

Spa Creek Waterfront | Pool & Parking

2 1
apartment , Annapolis
This Eastport condo offers waterfront living on Spa Creek, a mere 800 meters' walk to Downtown Annapolis and the US Naval Academy.
This two-bedroom flat accommodates up to four guests and features a communal swimming pool (seasonal), a fitness centre, and complimentary parking for two cars, with a covered deck providing water views.

Frequently Asked Questions about vacation rentals in Annapolis, MD

  • What should a first-time visitor not miss in Annapolis, MD?

    You definitely want to visit the United States Naval Academy, a beautiful campus with a rich history. A stroll around the historic City Dock is a must, where you can take in the beautiful views of the Chesapeake Bay and enjoy the lively atmosphere. And no trip to Annapolis is complete without exploring the charming streets of the historic downtown area, with its many shops, restaurants, and museums.
  • 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.

  • Which neighborhood in Annapolis, MD should you consider for a vacation rental?

    The historic district of Annapolis, known as Downtown Annapolis, is a popular choice for visitors. It's within walking distance of the City Dock, the State House, and many restaurants and shops. The neighbourhoods of Eastport and West Annapolis are also great options, offering a more residential feel with easy access to the harbour and other attractions.
  • What are the most popular Airbnbs in Annapolis, MD?

  • What are the top family-friendly attractions in Annapolis, MD?

    The Maryland State House, with its fascinating history and interactive exhibits, is a great choice for families. The Annapolis Maritime Museum and Park offers hands-on exhibits and activities for all ages. The Annapolis City Dock is a lovely spot for a family walk, with plenty of opportunities for ice cream and people-watching.
  • What are the best vacation rentals with a pool 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, from April to May and September to October. You'll find more affordable prices and fewer crowds compared to the peak season, which runs from June to August.
  • What are the best rentals for families and kids in Annapolis, MD?

  • What events or festivals should visitors check out in and around Annapolis, MD?

    The Annapolis City Dock is always buzzing with activity, especially during the annual Annapolis Sailboat Show in October. There's also the Annapolis Arts Festival in June, and the Chesapeake Bay Wine Festival in September.
  • What are the best rentals or Airbnbs with a jacuzzi in Annapolis, MD?

  • What are the best budget-friendly activities in Annapolis, MD?

    A walk around the historic City Dock is always free and offers stunning views of the Chesapeake Bay. The Naval Academy is also free to explore, with a beautiful campus and interesting exhibits. The Annapolis Farmers Market, held on Saturdays, is a great place to pick up fresh produce and local crafts.
  • What are the best restaurants with local dishes in Annapolis, MD?

    For a classic Maryland crab cake, head to O'Brien's, a local favourite. If you're looking for fresh seafood, try The Chart House, which has a beautiful waterfront location. For a more casual dining experience, try The Black Eyed Susan, known for its delicious crab soup and sandwiches.
  • What are the best walking or cycling routes in Annapolis, MD?

    The Annapolis Loop Trail, a 13 km paved trail, is a great option for both walking and cycling. It winds its way through the city, passing by the Naval Academy, the State House, and the City Dock. The scenic route along the Chesapeake Bay waterfront is also a popular choice for a leisurely stroll.
  • Are there pet-friendly attractions in Annapolis, MD?

    Many of the parks and green spaces in Annapolis are pet-friendly, including the City Dock and the Naval Academy grounds. The Annapolis Maritime Museum and Park also welcomes well-behaved dogs on leash.
  • What are the benefits of choosing a vacation rental in Annapolis, MD?

    Vacation rentals provide more space and privacy compared to hotels. They often offer kitchens and laundry facilities, which can be convenient for families or longer stays. Many vacation rentals are located in desirable neighbourhoods, offering easy access to local attractions.
  • What are the top sports attractions and facilities in Annapolis, MD?

    The US Naval Academy is home to a variety of sports teams, including football, basketball, and lacrosse. The Navy-Marine Corps Memorial Stadium hosts college football games and other events.

Destinations nearby

Best Annapolis, MD vacation rentals with a balcony

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking - Annapolis, MD
Annapolis, MD
01/01 – 01/02
$422/nighttotal: $13082 (31 )

Cozy 3br Annapolis Sleeps 6 Private Deck, Parking

1 2
house , Annapolis
This Annapolis property is located 2.2 kilometres from Sparrows Beach and 4.8 kilometres from Annapolis Harbour, offering convenient access to local attractions.
This holiday home, spanning 6 square metres, accommodates up to 10 guests and features air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and oven, a private deck, and free private parking.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
10 113 reviews
Annapolis, MD
01/01 – 01/02
$1170/nighttotal: $36270 (31 )

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free

2 2
apartment , Annapolis
This holiday home is located in Eastport, Annapolis, within a 1.6km walk of the Annapolis Maritime Museum, U.S. Naval Academy, and Spa Creek, making it ideal for exploring the city's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The 223 square metre home can accommodate up to 8 guests in its three bedrooms and has a sofa bed. Guests can enjoy a range of amenities, including a garden, a spa, a terrace, and a barbecue.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.8 27 reviews
Annapolis, MD
27/06 – 29/06
$3374/nighttotal: $6748 (2 )

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

5 2
apartment , Annapolis
This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque.
This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.
Two Historic Rowhomes In Downtown Annapolis - Annapolis, MD
Annapolis, MD
01/07 – 08/07
$1223/nighttotal: $8561 (7 )

Two Historic Rowhomes In Downtown Annapolis

4 2
apartment , Annapolis
This accommodation offers two connected historic row homes in downtown Annapolis, a short 100 metres from the Maryland Federation of Art and the French Soldiers Monument.
This family-friendly property, ideal for up to 12 guests, features four bedrooms, three bathrooms, two kitchens, and a patio, with in-unit laundry and air conditioning provided.

Best Annapolis, MD vacation rentals with parking

Usna Home Steps To Stadium Dog-friendly W Parking - Annapolis, MD
10 76 reviews
Annapolis, MD
03/12 – 06/12
$1570/nighttotal: $4710 (3 )

Usna Home Steps To Stadium Dog-friendly W Parking

3 10
apartment , Annapolis
This apartment is located in West Annapolis, just 1.7 kilometres from the Navy-Marine Corps Memorial Stadium, three blocks from shops and restaurants, and two to three blocks from the city centre. The apartment has excellent guest, location and cleanliness ratings.
This spacious three-bedroom home, with two bathrooms, offers 204 square metres of living space and comfortably accommodates up to 11 guests. The property features a private backyard with a hot tub, fire pit, BBQ grill, and a custom outdoor kitchen, as well as a swimming pool, jacuzzi, garden, spa, tennis court, and parking.
Bay View Studio Apartment - Annapolis, MD
9.9 151 reviews
Annapolis, MD
06/11 – 08/11
$621/nighttotal: $1242 (2 )

Bay View Studio Apartment

2 2
studio , Annapolis
This waterfront flat is situated in Annapolis, just a 1.6km walk from the Annapolis Sailing School and Annapolis Landing Marina, and within 5km of the Bay Bridge Market Place Shopping Center and Sparrows Beach. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The apartment has one bedroom, one bathroom, and can accommodate up to four guests comfortably. The 93 square meter space features a fully equipped kitchen, a fireplace, free Wi-Fi, a washing machine, and a terrace with stunning views of the Annapolis harbour. Guests can also enjoy the on-site amenities, including a swimming pool, jacuzzi, garden, and barbecue grills.
Beautiful Historic Home Next To City Dock + Usna - Annapolis, MD
10 42 reviews
Annapolis, MD
29/08 – 04/09
$572/nighttotal: $3432 (6 )

Beautiful Historic Home Next To City Dock + Usna

1 2
apartment , Annapolis
This four-bedroom, one-bathroom apartment in Annapolis city centre is situated just 91 metres from the United States Naval Academy's Gate 1 and City Dock, providing easy walking access to Main Street.
The property, sleeping up to six guests, boasts a large kitchen, a spacious living area with an 80-inch projector screen (Netflix and Apple TV included), and private backyard access; a king-size bed, twin bed, twin bunk beds, and a crib are provided.
Walking Distance To Navy Stadium! No Cleaning Fees! - Annapolis, MD
10 15 reviews
Annapolis, MD
11/09 – 19/09
$695/nighttotal: $5560 (8 )

Walking Distance To Navy Stadium! No Cleaning Fees!

3 4
apartment , Naval Academy
This West Annapolis apartment, situated less than 1.6km from the United States Naval Academy and a short walk from the Naval Academy Stadium, offers easy access to local restaurants and shops.
Sleeping eight guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, a garden, a spa, parking, and excellent internet access.
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