Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Freshly renovated 3-story home 1 block from USNA!

10.0 out of 10, Exceptional, (29)
"Best property we’ve stayed at in Annapolis by far. We look forward to our next stay. The property was spacious, well stocked, cozy and full of beautiful light! Central location to everything you need. Friendly neighborhood and great location. "
The price is AU$1,037
includes taxes & fees
3 Feb - 4 Feb
Freshly renovated 3-story home 1 block from USNA!

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (73)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Tranquility Awaits

10.0 out of 10, Exceptional, (14)
"It was an awesome short weekend stay for Army Navy game. Will consider staying here again for sure."
Tranquility Awaits

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (21)
"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "
Charming Historic Townhouse Steps From USNA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (15)
"Everything about this property was first class! We had an amazing stay in this comfortable home! Fully stocked kitchen. Body wash and shampoo in each bathroom. All the details covered. The location is awesome. Quick walk to downtown and the Naval Academy. The host was very accommodating and responsive. Can’t wait to stay again!"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (4)
"Property is great for families!!"
Brand New Spacious Luxury Home

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (139)
"We came up for the bowl game in Annapolis and this place offered a great place to stay near downtown and access to anywhere! The condo offered a clean comfortable place with all you need so close. "
Beautiful Condo - Water View Near City Dock

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (57)
"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"
Recently Renovated Annapolis Home - Conveniently Located

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (105)
"Great location. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Serene waterfront sunsets in this sprawling historic Annapolis home

9.6 out of 10, Exceptional, (28)
"Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving...
Serene waterfront sunsets in this sprawling historic Annapolis home

Private Waterfront Woods | Dock, Kayaks, Views

9.6 out of 10, Exceptional, (19)
"This property worked well for our large family. Most houses that sleep larger numbers don't come with a kitchen stocked for corresponding large numbers. But this kitchen was very well stocked with plenty of dishes and larger pots/pans for larger groups. "
Private Waterfront Woods | Dock, Kayaks, Views

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AU$1,964
includes taxes & fees
4 Feb - 5 Feb
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

9.8 out of 10, Exceptional, (9)
"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (28)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (52)
"Chip's place is very well located on West Street. We stayed over Christmas and it was easy to walk to my sister's house on Spa View and super nice to be above the top-notch coffee and baked goods at Curate. The place is perfectly laid out for two people/couples to each have their own space and bathroom. "
Chic Condo w/ Balcony in the Heart of 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.
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Other types of properties in Annapolis you may be interested in

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1006)
"Dog friendly"
The price is AU$238
includes taxes & fees
23 Feb - 24 Feb
Graduate by Hilton Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1006)
"Came for the Military Bowl. Rooms were comfortable and very quite. Staff was excellent and having a shuttle to and from the football stadium was an added plus. Centrally located."
The price is AU$185
includes taxes & fees
9 Feb - 10 Feb
DoubleTree by Hilton Hotel Annapolis

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1722)
"The room was spacious and the lights and heater were on, so it was very inviting when we walked in. The bed was comfortable. The hotel itself has the historic feel we enjoy when we stay in Annapolis. The front desk clerk and valet drivers were all gracious and professional. My husband and I had an excellent stay for our weekend getaway."
The price is AU$281
includes taxes & fees
10 Feb - 11 Feb
Historic Inns of 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.

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Annapolis Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Annapolis speak highly of the university campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What are some of the best holiday rentals that Annapolis has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This highly rated holiday home rental in Annapolis is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Annapolis are Freshly renovated 3-story home 1 block from USNA! and Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown.

How many holiday rentals will I find in Annapolis?

Expedia has 419 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Sandy Point State Park, or simply take in cultural attractions like Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Thurgood Marshall Memorial and Maryland State House are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.