Search Holiday Rentals in Annapolis

Search over 1 million properties and 550 airlines worldwide

Save 10% or more on select stays with Expedia Rewards

Most hotels are fully refundable. Because flexibility matters.

Top Holiday Rentals in Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

242 King George St, Annapolis, MD
Located in Historic District, this historic holiday home is within a 5-minute walk of Hammond-Harwood House and U.S. Naval Academy. Annapolis City Dock and Navy-Marine ...
5/5 Exceptional! (61 reviews)
Made me miss Annapolis.
"The owner communicated the check-in process clearly and what needed to be done before leaving the property. The house had a very old time feel which fits the area very well. We went for walks everyday down to Main Street to get coffee, eat and have drinks. Parking wasn't hard to find in the area. ..."

Reviewed on 13 Dec 2021

Charming garden row home, easy 4 block walk to the heart of Annapolis.
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

233 Mountain Laurel Ln, Annapolis, MD
The price is £320 per night from 19 Jan to 20 Jan
Located in the heart of Annapolis, this apartment building is 1.9 mi (3 km) from Naval Health Clinic and 3 mi (4.8 km) from Navy-Marine Corps Memorial Stadium. ...
5/5 Exceptional! (33 reviews)
The Perfect Place To Relax And Enjoy True Living
"If you're like so many of us out there looking to just transport yourself away from your everyday life and feel far enough away that you can breathe again but still want to be close to fun spots to go visit then this is your place! Not only did I plan my pre-wedding weekend here, but the owners of ..."

Reviewed on 22 Nov 2021

Waterfront Oasis of Annapolis Star
Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock

316 Burnside St, # 403, Annapolis, MD
Located in Eastport, this family-friendly Annapolis condo is within a 15-minute walk of Spa Creek and Annapolis City Dock. U.S. Naval Academy and Navy-Marine ...
4.7/5 Exceptional! (68 reviews)
Excellent 1 bedroom in Eastport!
"All the convenience of home with easy parking, elevator to 4th floor, and walking distance to downtown Anapolis!"

Reviewed on 16 Dec 2021

Beautiful Condo - Water View Near City Dock
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Beautiful Condo by the Naval Academy

Beautiful Condo by the Naval Academy

316 Burnside St, 304, Annapolis, MD
Located in Eastport, this condo is within a 15-minute walk of Spa Creek and Annapolis City Dock. U.S. Naval Academy and Navy-Marine Corps Memorial Stadium are ...
5/5 Exceptional! (1 review)
Beautiful space, great location, thoughtful touches
"I spent two nights in this property with my SO for New Year’s Eve festivities in Annapolis. Check in was pretty easy and the instructions provided were clear. Once inside the unit, we were very happy with the cleanliness and lack of any odors. The hosts were kind enough to leave a nice snack basket, ..."

Reviewed on 7 Jan 2022

Beautiful Condo by the Naval Academy
Cozy place close to the city dock

Cozy place close to the city dock

2010 Harbour gates dr, # 305, Annapolis, MD
Located in the heart of Annapolis, this historic apartment building is within 1 mile (2 km) of Anne Arundel Medical Center and Westfield Annapolis Mall. U.S. ...
4.8/5 Exceptional! (13 reviews)
Great Cozy Apartment Stay
"The apartment was exactly as advertised for a weekend getaway for my wife and I. It was clean, comfortable and just the right size for 2 people, but there is a sleeper sofa that can fit 2 more. The owner was easy to communicate with and we had no issues during our stay."

Reviewed on 12 Jan 2022

Cozy place close to the city dock
The Cottage on Spa Creek

The Cottage on Spa Creek

10 Cheston Ave, Annapolis, MD
Located in Historic District, this holiday home is within 1 mile (2 km) of Spa Creek, U.S. Naval Academy and Annapolis City Dock. Navy-Marine Corps Memorial ...
5/5 Exceptional! (44 reviews)
Wonderful!
"Another wonderful week at this perfect cottage! Great accommodations, perfect location, and amazing views of Spa Creek. Thank you!!"

Reviewed on 9 Nov 2021

The Cottage on Spa Creek
West Annapolis Hidden Gem

West Annapolis Hidden Gem

1603 West St, B, Annapolis, MD
This family-friendly apartment building is located in the city centre, within 1 mi (2 km) of Dr. Aris T. Allen Memorial, Maryland Hall for Creative Arts and ...
5/5 Exceptional! (1 review)
A great New Years!
"Four of us stayed here for the weekend of New Years. The kitchen was stocked with gadgets and coffee, anything we needed to clean, anything we needed to get cozy, etc. The apartment was adorable and the owners couldn’t have been friendlier!"

Reviewed on 9 Jan 2022

West Annapolis Hidden Gem
a charming 2 bedrooms home in historic Annapolis with parking!!

a charming 2 bedrooms home in historic Annapolis with parking!!

108 South St, Annapolis, MD
The price is £556 per night from 23 Jan to 24 Jan
Located in the centre of Annapolis, this family-friendly holiday home is within a 10-minute walk of Spa Creek and Annapolis City Dock. U.S. Naval Academy and ...
5/5 Exceptional! (29 reviews)
Wonderful home in a great location!
"A lovely home with very comfortable accommodations. We loved that there was convenient off-street parking. It is very well maintained and was quite quiet. We look forward to staying here again."

Reviewed on 27 Dec 2021

a charming 2 bedrooms home in historic Annapolis with parking!!
Anchor's Away in the Heart of Eastport!

Anchor's Away in the Heart of Eastport!

543 Second St, Unit A, Annapolis, MD
Located in Eastport, this apartment building is within a 10-minute walk of Annapolis Maritime Museum and U.S. Naval Academy. Annapolis City Dock and Navy-Marine ...
4.6/5 Exceptional! (8 reviews)
Perfect Getaway Weekend!
"Spacious and furnished beautifully in a great location. Sandra was great host who responded quickly. We will definitely stay here again."

Reviewed on 15 Oct 2021

Anchor's Away in the Heart of Eastport!
Jode's Retreat" Your Home Away From Home

Jode's Retreat" Your Home Away From Home

199 Clay St, Annapolis, MD
Located in Historic District, this historic holiday home is within 1 mile (2 km) of Peters Cove, U.S. Naval Academy and Annapolis City Dock. Navy-Marine Corps ...
4.5/5 Wonderful! (13 reviews)
"The area was calm and peaceful. The Hosts we're responsive and kind."

Reviewed on 3 Jan 2022

Jode's Retreat" Your Home Away From Home
Tranquility Awaits

Tranquility Awaits

530 Corbin Pkwy, Annapolis, MD
This family-friendly Annapolis apartment building is within 3 mi (5 km) of Westfield Annapolis Mall and Anne Arundel Medical Center. U.S. Naval Academy and Annapolis ...
5/5 Exceptional! (2 reviews)
First time in Annapolis
"New and clean home! The property was located on a quiet street where we could walk our dog. It had everything we needed! Nice and close to Annapolis!"

Reviewed on 28 Nov 2021

Tranquility Awaits
DOWNTOWN ANNAPOLIS LUXURY HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!

DOWNTOWN ANNAPOLIS LUXURY HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!

55 Amos Garrett Blvd, Annapolis, MD
Located in the centre of Annapolis, this family-friendly holiday home is within a 5-minute walk of Ballet Theater of Maryland, Spa Creek and Maryland Hall for ...
5/5 Exceptional! (130 reviews)
Amazing
"This property was amazing! We will have memories to tell forever! Thankyou so much!!!"

Reviewed on 24 Aug 2020

DOWNTOWN ANNAPOLIS LUXURY HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!
Annapolis Condominium in the Heart of Historic Downtown

Annapolis Condominium in the Heart of Historic Downtown

167 Conduit Street, Annapolis, MD
Located in Historic District, this condo is within a 10-minute walk of Maynard-Burgess House and Annapolis City Dock. U.S. Naval Academy and Navy-Marine Corps ...
4.8/5 Exceptional! (153 reviews)
"First off, Christina is very easy to contact and to get any information you need to make your stay the best. A lot of amenities included such as coffee and everything to add to your brew. Cutlery and other kitchen items for movie night or if you prefer to eat in. 1/2 block from Main Street in downtown ..."

Reviewed on 11 Jan 2022

Annapolis Condominium in the Heart of Historic Downtown
Bay View Studio Apartment

Bay View Studio Apartment

Annapolis, MD
This family-friendly Annapolis apartment building is located on the waterfront, within 3 mi (5 km) of Sparrows Beach, Historic Mount Moriah AME Church and Carrs ...
5/5 Exceptional! (5 reviews)
Beautiful view and clean, comfortable apartment
"The property is spacious, airy and was spotless when we arrived. Laura was welcoming and helpful but never intrusive. We would stay here again."

Reviewed on 23 Oct 2021

Bay View Studio Apartment
Chill in this Annapolis Cozy Cottage

Chill in this Annapolis Cozy Cottage

176 Acton Rd, Annapolis, MD
Located in the heart of Annapolis, this holiday home is 0.1 mi (0.1 km) from Spa Creek and within 3 miles (5 km) of U.S. Naval Academy and Navy-Marine Corps ...
Chill in this Annapolis Cozy Cottage
Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!

Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!

104 Eastern Ave, Annapolis, MD
Located in Eastport, this holiday home is within a 10-minute walk of Annapolis Maritime Museum and U.S. Naval Academy. Annapolis City Dock and Navy-Marine Corps ...
4.7/5 Exceptional! (66 reviews)
Great location
"This was a great place to stay with restaurants and entertainment within walking distance! Very clean, comfortable house!"

Reviewed on 11 Nov 2021

Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!
All Things ANNAPOLIS...

All Things ANNAPOLIS...

2134 Hideaway Ct, Annapolis, MD
Situated in Annapolis, this condo is 0.9 mi (1.5 km) from Anne Arundel Medical Center and within 3 miles (5 km) of Westfield Annapolis Mall and Navy-Marine Corps ...
4.3/5 Excellent! (6 reviews)
Awesome
"Easy & perfect"

Reviewed on 30 May 2021

All Things ANNAPOLIS...
Waterfront Oasis of Annapolis Blue

Waterfront Oasis of Annapolis Blue

233 Mountain Laurel Ln, Annapolis, MD
Located in the heart of Annapolis, this holiday home is 1.9 mi (3 km) from Naval Health Clinic and 3 mi (4.8 km) from Navy-Marine Corps Memorial Stadium. U.S. ...
5/5 Exceptional! (7 reviews)
Amazing property!
"The location, property, and owners are all amazing. My husband and our 3 kids stayed here for 3 nights and had the best time. It is a great location to anywhere you want to go. The owners are fantastic and even brought us ponchos and umbrellas when a huge storm hit as we were headed to a soccer game. ..."

Reviewed on 25 Oct 2021

Waterfront Oasis of Annapolis Blue
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

219 King George St, Annapolis, MD
Located in the centre of Annapolis, this family-friendly holiday home is within a 10-minute walk of Hammond-Harwood House, U.S. Naval Academy and Annapolis City ...
4.8/5 Exceptional! (27 reviews)
Christmas
"Thanks so much!"

Reviewed on 14 Jan 2022

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Quaint, light-filed haven in heart of downtown Annapolis

Quaint, light-filed haven in heart of downtown Annapolis

44 Murray Ave, Unit A, Annapolis, MD
Located in Murray Hill, this holiday home is within 1 mile (2 km) of Annapolis Civil Rights Plaque, U.S. Naval Academy and Annapolis City Dock. Navy-Marine Corps ...
5/5 Exceptional! (2 reviews)
Charm, comfort and location — the perfect couples stay in Annapolis
"We just finished a delightful two nights in this wonderfully redone (and exceptionally clean) bungalow. It’s an easy walk to colonial-era Annapolis, and all the restaurants, music venues, museums (counting the first floor of the statehouse) shops and waterfront strolling you could ask for. After ..."

Reviewed on 5 Oct 2021

Quaint, light-filed haven in heart of downtown Annapolis
Don't see what you're looking for?
See all available properties in Annapolis
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Annapolis you may be interested in

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3 out of 5
305 Harry S Truman Pkwy, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is £55 per night from 28 Jan to 29 Jan
Hilton Garden Inn Annapolis
Graduate Annapolis

Graduate Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is £79 per night from 30 Jan to 31 Jan
Graduate Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Holiday Apartments in Annapolis

Search for holiday rentals in Annapolis on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Annapolis using one of the methods below:

  • View our selection of featured holiday rentals in Annapolis
  • Use the map to find apartments and other holiday homes in the Annapolis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annapolis while they last

Look no further and take a look at our great range of rental properties in Annapolis

Frequently asked questions