Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Annapolis holiday rentals

Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$2,115
HK$5,306 total
includes taxes & fees
7 Jun - 8 Jun
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Outdoor dining

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is HK$1,340
HK$3,759 total
includes taxes & fees
31 May - 1 Jun
Chapel Gate 3BR Steps to City Dock & Naval Academy
Interior

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
The price is HK$1,505
HK$4,248 total
includes taxes & fees
31 May - 1 Jun
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$2,750
HK$5,367 total
includes taxes & fees
2 Jun - 3 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Exterior

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (52 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is HK$2,807
HK$3,611 total
includes taxes & fees
31 May - 1 Jun
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Property grounds

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.6 out of 10, Exceptional, (11 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is HK$2,997
HK$5,488 total
includes taxes & fees
1 Jun - 2 Jun
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (4 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is HK$3,040
HK$4,412 total
includes taxes & fees
1 Jun - 2 Jun
Fabulous 5-bedroom house with AC in charming Annapolis
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,904
HK$3,609 total
includes taxes & fees
1 Jun - 2 Jun
Waterfront Oasis of Annapolis Star
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,802
HK$4,672 total
includes taxes & fees
8 Jun - 9 Jun
Annapolis Retreat - 7 mins from downtown Annapolis!
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is HK$1,873
HK$4,958 total
includes taxes & fees
11 Jun - 12 Jun
Historic Row Home in Downtown Annapolis
Smart TV, fireplace, table football, ping pong

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is HK$2,500
HK$4,976 total
includes taxes & fees
3 Jun - 4 Jun
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is HK$3,042
HK$4,916 total
includes taxes & fees
2 Jun - 3 Jun
Adorable home steps from Navy stadium!
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$2,068
HK$5,653 total
includes taxes & fees
4 Jun - 5 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
4 bedrooms, iron/ironing board, travel cot, WiFi

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
The price is HK$3,495
HK$8,130 total
includes taxes & fees
11 Jun - 12 Jun
Two Historic Rowhomes in Downtown Annapolis
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is HK$3,526
HK$5,869 total
includes taxes & fees
1 Jun - 2 Jun
Secluded Cozy Cottage in Historic Downtown
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is HK$1,802
HK$3,529 total
includes taxes & fees
1 Jun - 2 Jun
Cozy 2br home w/ parking in downtown Annapolis
Exterior detail

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great location, well appointed home and good communication."
United States
Andrea K.
The price is HK$5,564
HK$9,811 total
includes taxes & fees
18 Jun - 19 Jun
Admiral's Abode - Charming Retreat
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is HK$2,108
HK$4,591 total
includes taxes & fees
10 Jun - 11 Jun
Charming Annapolis WaterVIEW Home
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is HK$2,339
HK$4,266 total
includes taxes & fees
6 Jun - 7 Jun
Annapolis Gem: Stylish and Cozy
Exterior

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.0 out of 10, Wonderful, (24 reviews)
"The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone."
United States
Ward U.
The price is HK$7,986
HK$14,330 total
includes taxes & fees
1 Jun - 2 Jun
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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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Top Annapolis Hotel Reviews

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

8/10 Good
"Derek was very helpful at the front desk."
Jackie 1-night trip
Posted 14 hours ago
Hilton Garden Inn Annapolis

Find out more about Annapolis

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

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

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Maryland Hall for Creative Arts, 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?

Charming Annapolis WaterVIEW Home: This highly rated holiday home rental in Annapolis is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 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 selection of games and 1 hot tub. Some other top choices in Annapolis are Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach and Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

How many holiday rentals will I find in Annapolis?

Expedia has 387 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 Annapolis Maritime Museum and Hammond-Harwood House. 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.