Find short term rentals in Annapolis, MD at the best prices
601 available short term rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Annapolis, MD
9.7 169 reviews
Annapolis, MD
03/12 – 06/12
$843/nighttotal: $2529 (3 )
Lots Free Parking, Hot Tub, Outdoor Oasis - Not Party House
1 10
apartment , Annapolis
This five-bedroom duplex is located in Annapolis, just a block from the Navy stadium and less than 1.6 kilometres from the city dock. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience. The spacious 223 square metre home offers a variety of amenities and activities for families and groups of up to 14 people, including a fenced-in backyard with a hot tub, a fully equipped kitchen, multiple TVs, a PlayStation, a Peloton, and a play area with musical instruments and exercise equipment.
10 1 review
Annapolis, MD
25/06 – 25/07
$2820/nighttotal: $84600 (30 )
Private Annapolis Retreat
1 2
apartment , Annapolis
This six-bedroom, five-bathroom flat in Annapolis offers a private setting just 5 kilometres from the city centre and the Navy Stadium, providing convenient access to local attractions. This spacious accommodation for up to 12 guests includes a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden, with pets welcome and internet provided for your convenience.
9.6 85 reviews
Annapolis, MD
07/08 – 09/08
$1596/nighttotal: $3192 (2 )
Three Miles From Historic Annapolis!
1 12
apartment , Arnold
This five-bedroom, three-bathroom apartment is located in Arnold, Maryland, just three miles from the Naval Academy and downtown Annapolis, offering easy access to both historic attractions and bustling city life. The property has received excellent ratings for location, cleanliness, and overall user experience, making it a popular choice for travellers. The spacious apartment comfortably accommodates up to 15 guests, with a layout perfect for family gatherings or group trips. Amenities include a fully equipped kitchen, a large garden, and a dedicated parking space, ensuring a comfortable and enjoyable stay.
Annapolis, MD
04/07 – 05/07
$605/nightfor 1 night
Robert Johnson 2 Doubles | Historic Inns
1 2
B&B , Annapolis
This Annapolis guesthouse, situated in the historic district, is within walking distance of the Maryland State House and the United States Naval Academy. Robert Johnson House, one of three historic buildings comprising this establishment, offers a one-bedroom, one-bathroom room sleeping up to four guests, featuring two double beds, a television, and complimentary Wi-Fi; valet parking is available nearby.
9.9 38 reviews
Annapolis, MD
06/08 – 10/08
$2429/nighttotal: $9716 (4 )
The Retreat @ Back Creek
1 10
apartment , Annapolis
This five-bedroom apartment is located in Eastport, a short walk from Annapolis' historic downtown and bustling City Dock. It has received excellent ratings for location, cleanliness and user experience. The apartment has three bathrooms and can accommodate up to sixteen guests. It offers a range of amenities, including a heated indoor pool, a spacious great room, a private patio, and a large recreation room with a bar and ping pong table.
9.9 94 reviews
Annapolis, MD
29/08 – 04/09
$323/nighttotal: $1938 (6 )
King George Hideaway 1st Floor
1 2
apartment , Annapolis
This one-bedroom flat is located in the centre of Annapolis, just 0.2km from the USNA Gate 2 and a short walk from Ego Alley and Main Street. The property has received excellent ratings for location, cleanliness, and overall experience. The flat comfortably accommodates four guests with a queen-size bed and a pull-out sofa. The kitchen is fully equipped with a fridge, freezer, microwave oven, and dishwasher, perfect for preparing meals during your stay.
10 4 reviews
Annapolis, MD
06/11 – 08/11
$578/nighttotal: $1156 (2 )
Bay Ridge House By Quiet Waters Park, Thomas Point Park
2 2
apartment , Annapolis
This modern home is located in a peaceful residential area in Annapolis, just a 5-minute walk from Quiet Waters Park and a 10-minute drive to the city centre. It has consistently received excellent user ratings, highlighting its appeal for travellers. The property offers 93 square metres of living space, including 2 bedrooms and 1 bathroom, comfortably accommodating up to 5 guests. Amenities include a fully equipped kitchen, air conditioning, parking, internet access, and a large yard, ensuring a comfortable and enjoyable stay.
9.9 27 reviews
Annapolis, MD
06/11 – 08/11
$454/nighttotal: $908 (2 )
Newly Renovated 1-bedroom On Spa Creek
1 2
apartment , Annapolis
This newly renovated Annapolis condo, situated in the Newport Condo Building just over the Spa Creek Bridge, offers easy walking access or a short water taxi journey to the city centre and is within easy reach of the United States Naval Academy. The one-bedroom apartment, sleeping two guests, boasts a full kitchen, rooftop pool (seasonal), dedicated parking, and stunning Spa Creek and Annapolis skyline views; key features include modern furnishings and a keypad entry system.
10 2 reviews
Annapolis, MD
12/07 – 30/08
$498/nighttotal: $24402 (49 )
Eastport Pied -A -Terre
1 2
apartment , Annapolis
This Annapolis apartment, conveniently located near the Eastport Bridge, offers easy walking access to both Annapolis city centre and Eastport. The one-bedroom flat features a fully equipped kitchen, in-unit laundry, a rooftop pool, and parking; it comfortably sleeps three guests and is perfect for couples seeking a cosy stay near the city's attractions.
9.9 530 reviews
Annapolis, MD
17/09 – 22/09
$104/nighttotal: $520 (5 )
Quail House - 1926 Four Bedroom Home In Annapolis
1 1
apartment , Annapolis
This charming guest house is situated in the Homewood neighbourhood of Annapolis, just a short distance from the historic district and major shopping areas. It enjoys a peaceful setting in a quiet, eclectic area with mature trees and streetlights. The guest house has received excellent ratings for its location, cleanliness, and overall experience. The accommodation offers a spacious yard and gardens, perfect for relaxation. It also includes a kitchenette with a fridge, microwave, and coffee/tea cart, as well as free parking just a short distance away. The owner, a local musician, is happy to offer insights into the Annapolis music scene and provide personalised recommendations for your stay.
9.6 63 reviews
Annapolis, MD
24/07 – 29/07
$728/nighttotal: $3640 (5 )
Walk To Waterfront & Usna From Eastport Gem With Fire Pit, Porch & Fenced-in Yard
2 3
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.
10 2 reviews
Annapolis, MD
17/09 – 22/09
$545/nighttotal: $2725 (5 )
Annapolis Town Center Cottage
2 1
apartment , Annapolis
This Annapolis Town Centre cottage is less than 1.6km from Annapolis's historic downtown area, the United States Naval Academy, and the waterfront. The two-bedroom, two-bathroom holiday home sleeps four guests and features a fully equipped kitchen with fridge, microwave, and dishwasher, plus air conditioning, parking for 2-3 vehicles, and a private backyard; nearby attractions include Maryland Hall for Creative Arts and the Ballet Theatre of Maryland.
Best family friendly Annapolis, MD Short term rentals
Among the 601 accommodations in Annapolis, MD, here are the 4 best family friendly rentals
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.
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).
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.
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
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.
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.
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.
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.
Frequently Asked Questions about short term rentals in Annapolis, MD
What are the best short term rentals in Annapolis, MD?
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.
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.
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.
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
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.
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.
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.
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.