Vacation Rentals in Annapolis, MD

938 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Annapolis, MD vacation rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

938 Vacation rentals and Airbnb in Annapolis, MD

Best family friendly Annapolis, MD vacation rentals

Among the 938 accommodations in Annapolis, MD, here are the 4 best family friendly rentals

Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 257 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
Dean Street's Lower Deck House! - Annapolis, MD
9.8 14 reviews

Dean Street's Lower Deck House!

apartment, Annapolis
This one-bedroom flat is situated in Annapolis' Historic District, offering immediate access to the U.S. Naval Academy, which is just 100 metres away, and is within easy walking distance of numerous local restaurants and shops.
This pet-friendly accommodation, suitable for up to three guests, features a private patio and a spacious backyard, with air conditioning and Wi-Fi provided, and is ideal for exploring the historic waterfront.
Pinecrest Bungalow - Annapolis, MD
10 4 reviews

Pinecrest Bungalow

house, Annapolis
This detached house is located in a water-privileged neighbourhood in Annapolis, 4 kilometres from Downtown Annapolis and 4.8 kilometres from the U.S. Naval Academy, with easy access to the Bay Bridge and major motorways.
This family-friendly property accommodates up to 7 guests across 3 bedrooms and a den, featuring a fenced garden with a furnished patio and fire pit, a dedicated exercise room, and essential amenities including air conditioning and high-speed internet.
Quiet Woodland Lodge W Community Beach Access & Large Private Deck - Annapolis, MD
8.0 1 review

Quiet Woodland Lodge W Community Beach Access & Large Private Deck

apartment, Annapolis
This Annapolis Roads residence is located at the end of a quiet cul-de-sac, providing a private retreat just 10 kilometres from downtown Annapolis and the U.S. Naval Academy.
This spacious 185 square metre flat offers four bedrooms, three bathrooms, and accommodates up to eight guests, featuring a water-privileged community with a private beach, playground, launching pier, and a furnished deck with a smoker grill and fire pit, alongside a two-story family room with a pellet stove and a lofted office space.

Best Annapolis, MD vacation rentals with a pool

Among the 938 accommodations in Annapolis, MD, here are the 4 best rentals with a pool

1st Floor Condo In Annapolis - Annapolis, MD
9.9 163 reviews

1st Floor Condo In Annapolis

apartment, Annapolis
This newly renovated studio flat is situated in Eastport, a quiet neighbourhood directly across Spa Creek from historic Annapolis, within a 1.6 km walk of the city centre and the US Naval Academy.
This pet-free apartment offers a fully equipped kitchen, high-speed Wi-Fi, free onsite parking, a secure building entrance, and a rooftop patio with a seasonal pool, with stunning views of the city.
Annapolis Waterfront Retreat W/ Pool, Dock & Sauna - Annapolis, MD
9.1 7 reviews

Annapolis Waterfront Retreat W/ Pool, Dock & Sauna

apartment, Annapolis
This waterfront flat in a quiet residential area of Annapolis offers a secluded retreat, located just 2.5 kilometres from the city centre.
This 4-bedroom, 4-bathroom residence accommodates up to 8 guests and features a private pool, pier with water access, and extensive gardens, with amenities including air conditioning, Wi-Fi, and a fitness centre.
Liberty Lookout - Annapolis, MD
9.6 11 reviews

Liberty Lookout

apartment, Annapolis
This waterfront condo in a quiet Eastport cul-de-sac offers Spa Creek views and is located 800 metres from downtown Annapolis and 1.3 kilometres from the U.S. Naval Academy.
This family-friendly apartment features two bedrooms and two bathrooms, accommodating up to seven guests, with amenities including air conditioning, a swimming pool, a furnished balcony, and off-street parking for two cars.
Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & Parking

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.

Frequently asked questions about holiday rentals in Annapolis, MD

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

    The Maryland State House is fascinating for kids, and the Annapolis Maritime Museum has lots of hands-on activities. For a fun day out, head to Sandy Point State Park, there's a great beach and plenty of space for kids to run around.
  • 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.

  • When is the best time to book a vacation rental in Annapolis, MD?

    Book your vacation rental as early as possible, especially if you're travelling during peak season, which is from May to October. You'll have more choice and potentially better prices.
  • What are the most popular Airbnbs in Annapolis, MD?

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

    The Annapolis Maritime Museum hosts a series of events throughout the year, and the annual Annapolis Arts Festival is a highlight in the summer. Check out the local calendar for other events like the Annapolis Boat Show.
  • What are the best vacation rentals with a pool in Annapolis, MD?

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

    Take a walk along the Annapolis City Dock, it's free and offers stunning views. The Naval Academy is also free to visit. For a picnic, head to Quiet Waters Park, it's a beautiful spot.
  • What are the best rentals for families and kids in Annapolis, MD?

    The best rentals for families and kids in Annapolis, MD are South River Park Apartment, 1b Annapolis Apartment and Cozy 2br Home W/ Parking In Downtown Annapolis.

  • What are the best restaurants with local dishes in Annapolis, MD?

    For fresh seafood, try Cantler's Riverside Inn or The Chart House. If you're looking for something more casual, try The Annapolis Market House, they have a great selection of local produce.
  • 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 cyclists, it's about 13km long and takes you past some of the city's most scenic spots. For a shorter walk, try the scenic path along the Spa Creek.
  • Are there pet-friendly attractions in Annapolis, MD?

    Many of the parks in Annapolis are pet-friendly, including Quiet Waters Park and the City Dock. You'll find plenty of dog-friendly restaurants and cafes too.
  • What are the benefits of choosing a vacation rental in Annapolis, MD?

    Vacation rentals offer more space and privacy than hotels. They can also be a more affordable option, especially if you're travelling with a group. Plus, you can often find rentals in great locations.
  • What are the top sports attractions and facilities in Annapolis, MD?

    The US Naval Academy is a big draw for sports fans, with its football and basketball teams. The city also has a number of public parks with sports facilities, like the Quiet Waters Park.

Popular destinations

Best Annapolis, MD holiday rentals with a balcony

Spa Creek Waterfront Pool & Parking - Annapolis, MD
10 1 review

Spa Creek Waterfront Pool & Parking

house, Annapolis
This Annapolis apartment offers direct waterfront access on Spa Creek, placing it a 13-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This two-bedroom, one-bathroom apartment, accommodating up to seven guests, features a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and private parking, with a floor area of 60 square metres.
Historic Annapolis Home Walk To Downtown 3br - Annapolis, MD
No reviews

Historic Annapolis Home Walk To Downtown 3br

apartment, Annapolis
This historic Annapolis dwelling, a spacious flat, is situated within walking distance of downtown, 4 kilometres from Annapolis Harbour and 2.7 kilometres from the Maryland State House, offering convenient access to the Navy-Marine Corps Memorial Stadium, just a 16-minute walk away.
This 170 square metre apartment accommodates up to nine guests, featuring one bedroom and two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, a terrace or balcony, a garden, and complimentary WiFi and private parking.
Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park - Annapolis, MD
9.5 11 reviews

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

apartment, Annapolis
This Bay Ridge flat is situated near Annapolis city centre and Quiet Waters Park, approximately 5.5 kilometres from Annapolis Harbour.
The 111-square-metre property, sleeping up to 11 guests, offers two bedrooms, one bathroom, free parking, a fully equipped kitchen, and a private patio; nearby attractions include Downtown Annapolis and Quiet Waters Park.
Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium - Annapolis, MD
9.2 20 reviews

Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium

apartment, Annapolis
This Annapolis Historic District property is less than 1.6km from Peters Cove and the United States Naval Academy, and within a 10-minute walk of Stanton School & Community Centre and the First Baptist Church.
The two-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, and parking; charcoal grills are available for outdoor cooking.

Best Annapolis, MD holiday rentals with parking

Capts Qrtrs - Awesome Downtown Annapolis Location! - Annapolis, MD
9.7 190 reviews

Capts Qrtrs - Awesome Downtown Annapolis Location!

apartment, Annapolis
This Annapolis apartment is ideally situated in the city centre, just a short walk from the United States Naval Academy and the bustling Main Street.
The self-catering property features a fully equipped kitchen, comfortable bedding for up to three guests, and modern amenities such as fast Wi-Fi and smart TVs.
Walk To Navy Stadium.dewey Drive
"The Boat House" - Annapolis, MD
9.9 35 reviews

Walk To Navy Stadium.dewey Drive "The Boat House"

apartment, Annapolis
This Annapolis houseboat, situated two blocks from the United States Naval Academy, offers easy access to Annapolis's attractions.
Sleeping up to ten guests, this three-level property boasts two kitchens, three bathrooms, four queen beds plus a queen sleeper sofa, multiple gathering spaces, high-speed internet, and access to a community pier for kayaking and paddleboarding.
Well-appointed 1 Bedroom, 1 Bath In Annap/eastport - Annapolis, MD
9.9 152 reviews

Well-appointed 1 Bedroom, 1 Bath In Annap/eastport

apartment, Annapolis
This one-bedroom flat is situated in Eastport, a lively neighbourhood in Annapolis, just a short walk from the Naval Academy and the downtown waterfront. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The flat is spacious and can comfortably accommodate up to four guests. Amenities include a well-equipped kitchen with a fridge, microwave oven, and dishwasher, a stylish bathroom, a comfortable king-size bed, a 50" TV, and a garden.
Historic Home With Parking Steps From Capital & Usna - Annapolis, MD
9.8 28 reviews

Historic Home With Parking Steps From Capital & Usna

apartment, Annapolis
This apartment is situated in the heart of Annapolis, just a short walk from the William Paca House and City Dock, making it ideal for exploring the city's historic charm. Guests have rated this property highly, making it a popular choice for travellers.
The flat has one bedroom and two bathrooms, comfortably accommodating up to four guests. The apartment offers modern amenities, including a fully equipped kitchen, air conditioning, a jacuzzi, and on-site parking, making it perfect for a relaxing and enjoyable stay.
©2026 cozycozy.com