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Annapolis, MD apartments
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720 Holiday apartments in Annapolis, MD

Best family friendly Annapolis, MD Holiday Apartments and Self Contained Accommodations

Among the 720 accommodations in Annapolis, MD, here are the 4 best family friendly holiday apartments

Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /Usna - Annapolis, MD
10 204 reviews

Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /Usna

apartment, Mayo
This waterfront property is located in Mayo, just 6 kilometres from Triton Beach, Sand Point Marsh, and South River Golf Links, making it ideal for exploring the area's natural beauty. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The spacious home can accommodate up to 8 guests and offers a range of amenities perfect for families and groups, including a private patio, fireplace, barbecue grills, a fully equipped kitchen, a fitness centre, a swimming pool, and a spa. Enjoy stunning views, direct access to the water, and easy access to local attractions.
Quiet Waterfront - Annapolis, MD
10 189 reviews

Quiet Waterfront

apartment, Annapolis
This Annapolis waterfront guesthouse, situated in Anne Arundel County, is approximately 8 kilometres from Annapolis city centre and 11 kilometres from City Dock, offering easy access to the city's attractions.
Sleeping six guests comfortably, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, on-site water activities including kayak and paddle boat use, and access to a gated community's clubhouse, swimming beach and tennis court.
Family Oasis|spa Shower|near Usna Stadium & Dta - Annapolis, MD
10 20 reviews

Family Oasis|spa Shower|near Usna Stadium & Dta

apartment, Annapolis
Nautical Oasis, a single-storey house in Annapolis, is situated less than 2.4km from the US Naval Academy Stadium, Anne Arundel Medical Center, and Annapolis city centre.
This three-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a private garden with fire pit, and a luxurious spa shower; guests can enjoy the entire house privately.
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 holiday home is situated less than 1.6km from 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.
The 111 square metre property comprises two bedrooms, one bathroom, and accommodates up to six guests, featuring a fully equipped kitchen, private patio, garden, parking, and free Wi-Fi.

Best Annapolis, MD Holiday Apartments and Self Contained Accommodations in Annapolis, MD with a pool

Among the 720 accommodations in Annapolis, MD, here are the 4 best apartments with a pool

Waterfront Oasis Of Annapolis Star - Annapolis, MD
10 87 reviews

Waterfront Oasis Of Annapolis Star

apartment, Arnold
This flat is situated in Annapolis, just a short distance from the Maryland World War II Memorial, Jonas Green State Park, and the Naval Health Clinic. It has received excellent reviews from previous guests.
The apartment is well-equipped and includes a kitchen with a fridge, microwave, and dishwasher. It also offers a range of amenities, such as a private pool, a fireplace, a terrace, and free Wi-Fi.
Usna King Stay! Private Hot Tub & In-ground Pool - Annapolis, MD
10 1 review

Usna King Stay! Private Hot Tub & In-ground Pool

apartment, Crownsville
This Crownsville flat is located in a district offering proximity to local landmarks, with precise location details available for convenient access to nearby attractions.
This spacious apartment accommodates up to 14 guests and features a kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning, a swimming pool, jacuzzi, and garden, making it ideal for groups seeking a comfortable stay.
Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat - Annapolis, MD
No reviews

Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat

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.
Spa Creek Condo Pool Deck & Parking - Annapolis, MD
No reviews

Spa Creek Condo Pool Deck & Parking

apartment, Annapolis
This Annapolis flat is located a 13-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This one-bedroom flat offers 60 square metres of space for up to seven guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, free WiFi, and private parking, with access to a communal swimming pool and a balcony.

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Best Annapolis, MD holiday apartments with air conditioning

Stay Retro Naptown - Annapolis, MD
9.9 82 reviews

Stay Retro Naptown

apartment, Annapolis
This Eastport house, situated near the Eastport Shopping Centre and a short walk from Annapolis city centre, offers easy access to the city's attractions.
Sleeping eight guests across four queen-bed bedrooms, this Annapolis property boasts two bathrooms, a fully equipped kitchen with fridge, freezer and microwave, in-unit laundry, a large garden with grill, screened porch, driveway parking for two cars, and a retro 1970s theme.
Nautical Cottage In Annapolis - Annapolis, MD
9.7 21 reviews

Nautical Cottage In Annapolis

apartment, Annapolis
This Annapolis cottage is situated in a peaceful neighbourhood, approximately 13km from Annapolis city centre and 6km from Route 50, offering easy access to both the historic district and major transport links.
The 900 sq ft property comprises two bedrooms, one bathroom, and a fully equipped kitchen including a freezer, microwave, and dishwasher; it comfortably sleeps four guests and boasts a garden and parking.
Chsapeake Bay Meets Nantucket, 5 Bedrooms,3.5 Bath - Annapolis, MD
10 1 review

Chsapeake Bay Meets Nantucket, 5 Bedrooms,3.5 Bath

apartment, Stevensville
This Stevensville flat offers direct bay views from its front and wildlife-rich Carter Creek vistas from its rear, situated across from the bay.
This waterside dwelling accommodates up to 13 guests across five bedrooms and 3.5 bathrooms, featuring air conditioning, internet, a kitchen, and abundant wildlife viewing opportunities on Carter Creek.
South River Waterfront | Pier, Hot Tub & Elevator - Annapolis, MD
10 5 reviews

South River Waterfront | Pier, Hot Tub & Elevator

apartment, Riva
"The Fritz" is a waterfront house located on the South River in Riva, Maryland, just 8 kilometers from Annapolis and its historic downtown. The accommodation has received excellent ratings for location, cleanliness, and overall experience.
The house has three bedrooms and four bathrooms, accommodating up to eight guests. Guests can enjoy a gourmet kitchen, a private pier, a hot tub, and spacious living areas with breathtaking river views.

Best pet-friendly Annapolis, MD holiday apartments

Among the 720 accommodations in Annapolis, MD, here are the 4 best pet friendly holiday apartments

Carriage House With Character! - Annapolis, MD
10 11 reviews

Carriage House With Character!

apartment, Riva
This Riva property, a 2-bedroom house sleeping 6, is situated approximately 16km from Annapolis city centre, offering easy access to Annapolis's historical attractions.
The self-catering dwelling boasts air conditioning, parking, internet access, and a fully equipped kitchen, perfect for exploring the Chesapeake Bay area.
Scenic Waterfront Retreat Mins To Annapolis W Panoramic Bay/bridge Views & Fenced-in Yard - Annapolis, MD
9.9 46 reviews

Scenic Waterfront Retreat Mins To Annapolis W Panoramic Bay/bridge Views & Fenced-in Yard

apartment, Highland Beach
This holiday home is situated in Arundel on the Bay, just 5 kilometres from Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park, offering a peaceful escape from the hustle and bustle of city life. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 3-bedroom, 2-bathroom property spans 124 square metres and comfortably accommodates up to 8 guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a garden, a terrace, a Jacuzzi, and free Wi-Fi.
Walk To Waterfront & Usna From Eastport Gem With Fire Pit, Porch & Fenced-in Yard - Annapolis, MD
9.6 64 reviews

Walk To Waterfront & Usna From Eastport Gem With Fire Pit, Porch & Fenced-in Yard

apartment, Annapolis
This Eastport holiday home is conveniently located within walking distance of the Annapolis Maritime Museum and the United States Naval Academy, and less than 1.6km from Spa Creek and the Kunta Kinte Plaque & Alex Haley Memorial.
The 79 square metre property offers two bedrooms, sleeping up to seven guests, and boasts a fully equipped kitchen, garden with barbecue, a spa, and free Wi-Fi; enjoy nearby attractions and on-site amenities.
Spacious 5 Br House - 5 Min Walk To N-mc Stadium! - Annapolis, MD
9.8 6 reviews

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

apartment, Annapolis
This Annapolis holiday home, situated in the Germantown neighbourhood, is located two blocks from the Navy-Marine Corps Memorial Stadium and an eight-minute drive (approximately 6.4km) from the United States Naval Academy and Annapolis city centre.
This spacious property boasts 242 square metres of floor area, offering five bedrooms (three main bedrooms and two bunk rooms in the basement), accommodating up to 15 guests and featuring amenities such as a jacuzzi bath, foosball table, and a fully enclosed garden.
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