Find short term rentals in Annapolis, MD at the best prices

601 available short term rental offers

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Annapolis, MD short term rentals
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Best Short term and Weekly rentals in Annapolis, MD

Best family friendly Annapolis, MD Short term rentals

Among the 601 accommodations in Annapolis, MD, here are the 4 best family friendly rentals

Historic Annapolis Charmer <1mile To Nmc Stadium - Annapolis, MD
9.8 7 reviews
Annapolis, MD
12/07 – 13/07
$2596/nightfor 1 night

Historic Annapolis Charmer <1mile To Nmc Stadium

6 2
apartment , Annapolis
This Annapolis apartment, situated a short walk from the city centre and a short drive (approximately 1-2km) from the United States Naval Academy and Navy-Marine Corps Stadium, offers convenient access to Annapolis's key attractions.
This spacious 465 square metre dwelling boasts five bedrooms, five bathrooms, and sleeps up to 21 guests, featuring multiple living areas, a well-equipped kitchen, a garden, tennis court, parking, and proximity to Ego Alley, Great Frogs Winery, and Helen Avalynne Tawes Garden.
Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking,  Pets+kids - Annapolis, MD
10 52 reviews
Annapolis, MD
31/07 – 02/08
$763/nighttotal: $1526 (2 )

Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking, Pets+kids

2 4
apartment , Annapolis
This three-bedroom Annapolis apartment, situated in the Admiral Heights neighbourhood, is less than 1km from People's Brewer Hill Cemetery and 2.6km from the United States Naval Academy.
The self-catering property sleeps six, boasts a private fenced yard, patio, fireplace, fully equipped kitchen, and access to community gardens and barbeque facilities; nearby attractions include the Helen Avalynne Tawes Garden (within a 15-minute drive).
King George Downtown Annapolis Getaway - Annapolis, MD
9.6 158 reviews
Annapolis, MD
29/08 – 04/09
$521/nighttotal: $3126 (6 )

King George Downtown Annapolis Getaway

3 2
apartment , Annapolis
This flat is situated in the centre of Annapolis, just 2.2 kilometres from the harbour and within easy reach of Baltimore’s attractions. It has received excellent ratings for location, cleanliness and overall experience.
The accommodation offers a comfortable and well-equipped space, including a fully fitted kitchen, a balcony and a garden. Guests can enjoy free Wi-Fi, air conditioning, parking and barbecue facilities.
Historic Downtown Annapolis Gem Steps To Usna And Main St With Private Patio And Parking - Annapolis, MD
10 26 reviews
Annapolis, MD
29/06 – 01/07
$1127/nighttotal: $2254 (2 )

Historic Downtown Annapolis Gem Steps To Usna And Main St With Private Patio And Parking

3 4
apartment , Annapolis
This charming, fully-renovated house is located in the Historic District of Annapolis, just 0.4 km from the US Naval Academy, St. John's College, and the state capital building. The property has received excellent guest reviews, so you can be sure of a comfortable and enjoyable stay.
The house has three bedrooms, comfortably sleeping up to eight guests. The property offers a range of amenities, including a fully equipped kitchen, a spacious garden, a balcony with picturesque views, and a private backyard with a fire pit.

Best Annapolis, MD lodging with a balcony

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis - Annapolis, MD
Annapolis, MD
06/08 – 10/08
$2159/nighttotal: $8636 (4 )

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis

6 10
apartment , Annapolis
This spacious six-bedroom house is located in Annapolis's Admiral Heights district, offering convenient access to Navy-Marine Corps Memorial Stadium (800 metres) and the U.S. Naval Academy and Historic Downtown Annapolis (both 3.2 kilometres) making it ideal for visitors.
This dog-friendly property boasts 290 square metres of living space, accommodating up to 13 guests with multiple living areas, extensive outdoor entertaining spaces including a screened porch with a television, and driveway parking for four vehicles.
Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown - Annapolis, MD
10 26 reviews
Annapolis, MD
25/06 – 28/06
$1455/nighttotal: $4365 (3 )

Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown

5 2
apartment , Highland Beach
This Highland Beach waterfront property, a five-minute walk from the Chesapeake Bay and historic Highland Beach, is situated a short drive from Annapolis city centre, the United States Naval Academy, and Quiet Waters Park.
The five-bedroom, four-bathroom house sleeps ten guests, boasts a well-equipped kitchen, two spacious decks with stunning waterfront views, a tennis court, ample parking, and offers access to free Wi-Fi and a home office/fitness room.
Downtown Annapolis Duke's House - Annapolis, MD
10 1 review
Annapolis, MD
24/07 – 29/07
$2738/nighttotal: $13690 (5 )

Downtown Annapolis Duke's House

1 3
apartment , Annapolis
This Annapolis Historic District house, a short walk (under 1.6km) from Spa Creek and the United States Naval Academy, and less than 0.8km from the Maynard-Burgess House and the Kunta Kinte Plaque & Alex Haley Memorial, offers convenient access to key Annapolis attractions.
This four-bedroom, four-bathroom property sleeps nine guests and includes a fully equipped kitchen, private garden, on-site parking, and a washing machine; enjoy a smoke-free stay in this comfortable family home.
Spectacular Location: State Circle Apartment - Annapolis, MD
10 17 reviews
Annapolis, MD
11/09 – 19/09
$602/nighttotal: $4816 (8 )

Spectacular Location: State Circle Apartment

2 4
apartment , Annapolis
This two-bedroom flat is situated in Annapolis' Historic District, just a kilometre from the Thurgood Marshall Memorial and the US Naval Academy, and 500 metres from the Colonial Players theatre. It has been rated excellent by previous guests.
The 74 square metre flat comfortably accommodates up to seven guests. It includes a fully equipped kitchen, two bathrooms, a washing machine, a sofa bed, and a TV, making it ideal for a comfortable stay in Annapolis.

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Best Annapolis, MD lodging with a kitchen

Annapolis Cottage - Annapolis, MD
9.8 34 reviews
Annapolis, MD
29/08 – 04/09
$298/nighttotal: $1788 (6 )

Annapolis Cottage

1 2
apartment , Highland Beach
This Highland Beach apartment offers a treehouse-like outdoor experience, just a short walk from a neighbourhood park and minutes from historic downtown Annapolis.
This one-bedroom flat accommodates up to four guests, featuring a king-size bed, a queen-size pull-out sofa, a full-sized kitchen, a bathtub, air conditioning, and parking.
Eastport Craftsman Retreat - Annapolis, MD
10 5 reviews
Annapolis, MD
06/08 – 10/08
$1127/nighttotal: $4508 (4 )

Eastport Craftsman Retreat

1 10
apartment , Annapolis
This spacious Eastport house in Annapolis, Maryland is located minutes from the Eastport Shopping Centre and a short walk from the downtown area.
Sleeping up to ten guests, this five-bedroom, 2.5-bathroom property boasts a fully equipped kitchen, garden, parking, and air conditioning; its sustainable design includes geothermal heating and cooling, and solar energy.
1 Block To Downtown Annapolis | 3br Retreat - Annapolis, MD
9.2 10 reviews
Annapolis, MD
01/07 – 08/07
$397/nighttotal: $2779 (7 )

1 Block To Downtown Annapolis | 3br Retreat

3 2
apartment , Annapolis
This Annapolis flat offers a prime location, situated just 100 metres from historic Downtown Annapolis, providing easy walking access to the US Naval Academy, City Dock, and the Maryland State House.
This three-bedroom apartment accommodates up to six guests and features a fully equipped kitchen, air conditioning, and in-unit laundry, making it ideal for exploring Annapolis's shops and dining.
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.9 67 reviews
Annapolis, MD
25/06 – 28/06
$778/nighttotal: $2334 (3 )

Cute Bungalow Blocks To Stadium

2 2
apartment , Annapolis
This stylish two-bedroom house is located in Annapolis' Germantown neighbourhood, just 2.4 kilometres from the Navy-Marine Corps Memorial Stadium and an 8-minute drive from the USNA and downtown Annapolis. This property enjoys excellent ratings for location, cleanliness, and user experience.
The house has two bedrooms and one bathroom, accommodating up to six guests. It offers a fully equipped kitchen, a private garden, and a covered outdoor eating area, perfect for enjoying meals al fresco.

Best Annapolis, MD lodging with laundry available

Charming Cottage With Parking. Easy Walk To Downtown. - Annapolis, MD
9.9 283 reviews
Annapolis, MD
29/06 – 01/07
$523/nighttotal: $1046 (2 )

Charming Cottage With Parking. Easy Walk To Downtown.

1 4
apartment , Annapolis
This charming cottage is located on a quiet residential street in Annapolis Art District, just a short walk (less than 1 kilometre) from the Naval Academy, Navy Stadium, shops, bars, restaurants, and City Docks. The property has consistently received excellent reviews for its location, cleanliness, and overall experience.
The cottage offers 117 square metres of living space, with two bedrooms, two bathrooms, and a capacity for six guests. It is fully equipped with modern amenities, including a garden with a patio set and BBQ grill, a jacuzzi, and parking for two vehicles.
The Heart Of Annapolis At Capital Views, W Free Off-site Parking & Patio At Historic Home - Annapolis, MD
9.9 88 reviews
Annapolis, MD
29/06 – 01/07
$945/nighttotal: $1890 (2 )

The Heart Of Annapolis At Capital Views, W Free Off-site Parking & Patio At Historic Home

3 4
apartment , Annapolis
This charming house is located in Annapolis' Historic District, just a short walk from the U.S. Naval Academy, Ellen O. Moyer Nature Park, Maynard-Burgess House, and the Banneker Douglass Museum. It has received excellent ratings for location, cleanliness, and user experience.
The property offers 186 square metres of space with four bedrooms, comfortably accommodating up to eight guests. Enjoy the garden, patio, barbecue grills, and modern conveniences like free Wi-Fi, a fully equipped kitchen, and a spa.
Historic + Modern Home | Just Steps To Waterfront - Annapolis, MD
10 43 reviews
Annapolis, MD
12/07 – 13/07
$718/nightfor 1 night

Historic + Modern Home | Just Steps To Waterfront

1 2
apartment , Annapolis
This Annapolis Fleet Street townhouse, a short walk from City Dock and the United States Naval Academy, offers a prime location in the historic district.
The two-bedroom, one-bathroom apartment sleeps seven, includes a fully equipped kitchen with dishwasher and modern amenities such as Wi-Fi and in-unit laundry, and family-friendly extras are available on request.
Downtown Pinkney House W/parking - Annapolis, MD
9.8 53 reviews
Annapolis, MD
06/11 – 08/11
$827/nighttotal: $1654 (2 )

Downtown Pinkney House W/parking

1 2
apartment , Annapolis
This Annapolis townhome enjoys a prime downtown location, within easy walking distance of the United States Naval Academy and Annapolis's main attractions.
The two-bedroom, two-and-a-half-bathroom property offers a fully equipped kitchen, rooftop patio with water views, and dedicated parking – a significant advantage in Annapolis – comfortably sleeping four guests.
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