A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

Annapolis Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Annapolis holiday rentals

A wooden dock extending into a calm body of water with boats docked at the end.

1. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is HK$1,962
HK$3,766 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 2br home w/ parking in downtown Annapolis
A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

2. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
The price is HK$1,436
HK$4,952 total
includes taxes & fees
19 Oct - 20 Oct
Annapolis Charmer - Perfect Location
A kitchen with a wooden countertop, a stove, and a refrigerator.

3. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
The price is HK$1,829
HK$3,338 total
includes taxes & fees
14 Oct - 15 Oct
18th Cent. Charm in Historic Downtown Annapolis
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

4. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
The price is HK$1,554
HK$9,895 total
includes taxes & fees
20 Oct - 21 Oct
Luxe Row Home Steps to USNA Gate 3!
Interior

5. Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is HK$1,554
HK$4,491 total
includes taxes & fees
20 Oct - 21 Oct
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

6. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (2 reviews)
"The location of this home is stellar! Every shop and restaurant is within walking distance. The home is super clean and charming. Tastefully furnished both in style and comfort. The kitchen was fully stocked. The bathrooms are updated and beautiful. The showers are fantastic! Eric was a gem to work with!"
United States
gina w.
The price is HK$1,460
HK$4,428 total
includes taxes & fees
20 Oct - 21 Oct
Historic Row Home in Downtown Annapolis
A living room with a dining table, two sofas, a coffee table, and a patterned rug.

7. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
The price is HK$1,546
HK$4,030 total
includes taxes & fees
4 Nov - 5 Nov
Chapel Gate 3BR Steps to City Dock & Naval Academy
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

8. Dean Street's Lower Deck House!

Dean Street's Lower Deck House!
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
The price is HK$1,749
HK$3,883 total
includes taxes & fees
18 Oct - 19 Oct
Dean Street's Lower Deck House!
A modern kitchen with a central island, built-in oven, and microwave.

9. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is HK$1,624
HK$4,185 total
includes taxes & fees
19 Oct - 20 Oct
Cute bungalow blocks to Stadium
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

10. Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
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$1,336
HK$3,786 total
includes taxes & fees
10 Nov - 11 Nov
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

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

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (22 reviews)
"Accommodating hosts, charming house and great location! "
United States
Scott C.
The price is HK$2,299
HK$3,766 total
includes taxes & fees
9 Nov - 10 Nov
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

12. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Great property. Big back yard. Nice walk to downtown and campus."
United States
Stephen P.
The price is HK$2,883
HK$6,660 total
includes taxes & fees
19 Oct - 20 Oct
Eastport 3 bedroom Cottage: Walk to Downtown
A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

13. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is HK$3,413
HK$7,234 total
includes taxes & fees
19 Oct - 20 Oct
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

14. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is HK$2,433
HK$6,134 total
includes taxes & fees
20 Oct - 21 Oct
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

15. Mins to DTA - King Beds - Parking

Mins to DTA - King Beds - Parking
Annapolis
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
The price is HK$2,642
HK$5,194 total
includes taxes & fees
20 Oct - 21 Oct
Mins to DTA - King Beds - Parking
Stylish kitchen with open layout and island seating

16. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is HK$1,639
HK$3,943 total
includes taxes & fees
14 Oct - 15 Oct
Pool Loft Suite | Bay Access & Beach Passes
A two-story house with a covered patio, a garage, and a well-maintained lawn.

17. 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, (55 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is HK$3,002
HK$3,914 total
includes taxes & fees
19 Oct - 20 Oct
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

18. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is HK$1,339
HK$3,897 total
includes taxes & fees
2 Nov - 3 Nov
Upscale Condo in Annapolis w/Private Parking
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.

19. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is HK$2,213
HK$3,344 total
includes taxes & fees
5 Nov - 6 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A multi-story residential building with solar panels on the roof, a front porch, and a well-maintained garden.

20. Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
10.0 out of 10, Exceptional, (4 reviews)
"What a great experience! The property is exactly as listed and was perfect for our grown family traveling together. We had everything we needed for evenings in, and 5 mins away from the heart of Annapolis and all the restaurants and shops there. Perfectly located to explore Annapolis and the surrounding area. Communication from the hosts was excellent, I would definitely recommend this property."
United States
Kim A.
The price is HK$3,422
HK$5,624 total
includes taxes & fees
12 Nov - 13 Nov
Adorable home steps from Navy stadium!
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Personnel kind and quiet"
JOSE 1-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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 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 Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This highly rated holiday home rental in Annapolis is located near the beach, 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital.

How many holiday rentals will I find in Annapolis?

Expedia has 381 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 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.