Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is NZ$472
includes taxes & fees
22 July - 23 July
Cozy Home in Beautiful Annapolis

Mins to DTA - King Beds - Parking

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
The price is NZ$907
includes taxes & fees
22 July - 23 July
Mins to DTA - King Beds - Parking

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

10.0 out of 10, Exceptional, (6)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
The price is NZ$976
includes taxes & fees
14 July - 15 July
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Fisher House: Steps From USNA + Covered Parking!

10.0 out of 10, Exceptional, (11)
"The location is perfect!"
The price is NZ$1,049
includes taxes & fees
15 July - 16 July
Fisher House: Steps From USNA + Covered Parking!

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is NZ$1,359
includes taxes & fees
14 July - 15 July
Charming Cottage with Hot Tub 1 Block from the Bay

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
Cute bungalow blocks to Stadium

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is NZ$1,028
includes taxes & fees
21 July - 22 July
Annapolis Retreat - 7 mins from downtown Annapolis!

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is NZ$816
includes taxes & fees
15 July - 16 July
Neptune by the Water

Dean Street's Lower Deck House!

Dean Street's Lower Deck House!

vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

9.6 out of 10, Exceptional, (12)
"My sisters and I enjoyed a wonderful weekend in this recently renovated townhouse steps away from downtown - a plus for those of us with cranky knees! Immaculate with crisp comfy beds & linens, two full bathrooms and three bedrooms, we had plenty of room to relax and share a great visit. Smooth check in and check out. Friendly neighbors. Perfect location. relax "
The price is NZ$689
includes taxes & fees
14 July - 15 July
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy

Historic Annapolis Charmer <1Mile to NMC Stadium

9.8 out of 10, Exceptional, (6)
"The home was beautiful and spacious. The host was wonderful and communicated with us very well. Would recommended for a large group! "
The price is NZ$2,227
includes taxes & fees
16 July - 17 July
Historic Annapolis Charmer <1Mile to NMC Stadium

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

9.0 out of 10, Wonderful, (2)
"My mom and I visited with 8 grandchildren as part of their Christmas present. We checked out the Naval Academy, monuments in DC, and a football bowl game. The kids enjoyed the new adventures!"
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

★ Midcentury Modern Getaway ★ Prime Location ★

10.0 out of 10, Exceptional, (33)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
The price is NZ$1,069
includes taxes & fees
13 July - 14 July
★ Midcentury Modern Getaway ★ Prime Location ★

Historic Row Home 1 Block from Gate 1 at USNA!

The price is NZ$1,153
includes taxes & fees
14 July - 15 July
Historic Row Home 1 Block from Gate 1 at USNA!

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (51)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
The price is NZ$1,376
includes taxes & fees
3 Aug - 4 Aug
Charming Annapolis WaterVIEW Home

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (11)
"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 NZ$2,629
includes taxes & fees
15 July - 16 July
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (69)
"Comfortable, clean home. Convenient walking distance to historic downtown Annapolis. "
The price is NZ$708
includes taxes & fees
29 July - 30 July
Cozy 2br home w/ parking in downtown Annapolis

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

10.0 out of 10, Exceptional, (17)
"Accommodating hosts, charming house and great location! "
The price is NZ$1,028
includes taxes & fees
31 July - 1 Aug
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Naptown Villa House S

10.0 out of 10, Exceptional, (1)
"Incredible accomodations at Naptown Villa. Perfect location, beautiful setting, lovely home for the holiday weekend. "
Naptown Villa House S
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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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?

Quiet Relaxing Waterfront Suisse Chalet: This highly rated holiday home rental in Annapolis is located on a lake, and has a fireplace, a balcony 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 can relax into your holiday with a private garden and 1 hot tub. Some other top choices in Annapolis are Charming Historic Townhouse Steps From USNA and Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! .

How many holiday rentals will I find in Annapolis?

Expedia has 439 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Carrs Beach and Maryland Quiet Waters Park, or simply take in cultural attractions like Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Maryland State House and William Paca 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.