Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Annapolis holiday rentals

Outdoor pool, a heated pool

Apartment in Annapolis

Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,619
HK$3,236 total
includes taxes & fees
10 Mar - 11 Mar
Waterfront Oasis of Annapolis Star
Games room

Holiday Home in Eastport

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is HK$1,564
HK$2,835 total
includes taxes & fees
23 Mar - 24 Mar
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Outdoor dining

Holiday Home in Arundel on the Bay

Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (62 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
Charming Annapolis WaterVIEW Home
Marina

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is HK$2,150
HK$5,857 total
includes taxes & fees
2 Mar - 3 Mar
Fisher House: Steps From USNA + Covered Parking!
Smart TV, fireplace, table football, ping pong

Holiday Home in Homewood

Historic Annapolis Charmer <1Mile to NMC Stadium
9.8 out of 10, Exceptional, (6 reviews)
"We had 11 people in our group and this house was the perfect size for gathering and sleeping comfortably. Great accommodations, easy to get downtown and around. Definitely recommend"
United States
Priscilla M.
The price is HK$5,025
HK$10,105 total
includes taxes & fees
1 Mar - 2 Mar
Historic Annapolis Charmer <1Mile to NMC Stadium
Property grounds

Holiday Home in Cape Saint Claire

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
9.2 out of 10, Wonderful, (5 reviews)
The price is HK$3,519
HK$6,160 total
includes taxes & fees
28 Feb - 1 Mar
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Marina

Holiday Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,348
HK$3,792 total
includes taxes & fees
1 Mar - 2 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Beach nearby, sun-loungers, beach towels

Holiday Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$1,759
HK$4,074 total
includes taxes & fees
2 Mar - 3 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is HK$1,936
HK$3,776 total
includes taxes & fees
27 Feb - 28 Feb
Annapolis Gem: Stylish and Cozy
Microwave, oven, stovetop, dishwasher

Holiday Home in Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
8.0 out of 10, Very good, (3 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is HK$2,753
HK$4,101 total
includes taxes & fees
2 Mar - 3 Mar
Fabulous 5-bedroom house with AC in charming Annapolis
Exterior

Holiday Home in Historic District

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is HK$6,459
HK$10,920 total
includes taxes & fees
2 Mar - 3 Mar
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Exterior

Apartment in Admiral Heights

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (48 reviews)
"Convenient location, very clean, beautiful yard for a pet friendly visit. We had a great time! Would go back again. "
United States
Jackie C.
The price is HK$2,780
HK$3,624 total
includes taxes & fees
28 Feb - 1 Mar
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Marina

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is HK$2,555
HK$4,606 total
includes taxes & fees
15 Mar - 16 Mar
Secluded Cozy Cottage in Historic Downtown
Dining

Condo in Historic District

Historic Row Home in Downtown Annapolis
The price is HK$1,150
HK$5,618 total
includes taxes & fees
1 Mar - 2 Mar
Historic Row Home in Downtown Annapolis
Smart TV, fireplace, table football, ping pong

Holiday Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is HK$1,514
HK$3,759 total
includes taxes & fees
3 Mar - 4 Mar
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is HK$1,259
HK$4,528 total
includes taxes & fees
2 Mar - 3 Mar
Neptune by the Water - Pet Friendly Fenced Yard
Interior

Holiday Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,243
HK$4,065 total
includes taxes & fees
1 Mar - 2 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
Fridge, microwave, oven, stovetop

Holiday Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
The price is HK$1,956
HK$6,358 total
includes taxes & fees
1 Mar - 2 Mar
All Star Annapolis Retreat - Walk to Stadium
Interior

Condo in Historic District

Upscale Condo in Annapolis w/Private Parking
10.0 out of 10, Exceptional, (2 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is HK$1,672
HK$4,010 total
includes taxes & fees
11 Mar - 12 Mar
Upscale Condo in Annapolis w/Private Parking
TV, offices

Holiday Home in Annapolis

Wright's Cottage- Pet's Welcome & EV Charging
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is HK$1,293
HK$2,793 total
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Nice pl"
Christian 1-night trip
Posted 17 hours ago
SpringHill Suites by Marriott 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:

  • 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

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This highly rated holiday home rental in Annapolis offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Annapolis is Spacious Luxe USNA Home - Pool, Hot Tub, Grill.

How many holiday rentals will I find in Annapolis?

Expedia has 384 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Bay Ridge Beach, or simply take in cultural attractions like Hammond-Harwood House and Maryland Hall for Creative Arts. 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.