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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Annapolis holiday rentals

1. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is HK$1,885
HK$4,481 total
includes taxes & fees
1 Sept - 2 Sept
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A kitchen with a wooden countertop, a stove, and a refrigerator.

2. 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$1,827
HK$3,352 total
includes taxes & fees
29 Aug - 30 Aug
18th Cent. Charm in Historic Downtown Annapolis
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

3. 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$1,595
HK$3,507 total
includes taxes & fees
31 Aug - 1 Sept
Dean Street's Lower Deck House!
A lobby with a reception desk, a blue sofa, a plant, and a door leading outside.

4. New Downtown Annapolis Condo With Free Parking

New Downtown Annapolis Condo With Free Parking
Historic District
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful property, excellent location, and had a wonderful visit to Annapolis!"
United States
Darby F.
The price is HK$1,481
HK$3,315 total
includes taxes & fees
31 Aug - 1 Sept
New Downtown Annapolis Condo With Free Parking
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

5. 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$2,806
HK$5,799 total
includes taxes & fees
9 Sept - 10 Sept
Upscale Condo in Annapolis w/Private Parking
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (85 reviews)
"Thank you for the stay! We loved the location."
United States
Mary G.
The price is HK$1,764
HK$3,521 total
includes taxes & fees
31 Aug - 1 Sept
Cozy 2br home w/ parking in downtown Annapolis
A swimming pool with a waterfall feature surrounded by lush greenery.

7. Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (87 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is HK$1,728
HK$3,373 total
includes taxes & fees
1 Sept - 2 Sept
Waterfront Oasis of Annapolis Star
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

8. 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)
"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."
United States
Christine A.
The price is HK$1,544
HK$9,874 total
includes taxes & fees
30 Aug - 31 Aug
Luxe Row Home Steps to USNA Gate 3!
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

9. 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$2,054
HK$5,693 total
includes taxes & fees
31 Aug - 1 Sept
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

10. 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$1,505
HK$4,450 total
includes taxes & fees
31 Aug - 1 Sept
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.

11. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is HK$1,458
HK$4,450 total
includes taxes & fees
30 Aug - 31 Aug
Historic Row Home in Downtown Annapolis
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

12. 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, (21 reviews)
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with a central island, stainless steel range hood, and a built-in oven.

13. Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
Walk to the stadium! - Lighthouse on Glenwood
A modern kitchen with a central island, built-in oven, and microwave.

14. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is HK$1,623
HK$4,172 total
includes taxes & fees
2 Sept - 3 Sept
Cute bungalow blocks to Stadium
A patio with a round table and chairs, a grill, and a wooden fence.

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

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is HK$1,599
HK$4,097 total
includes taxes & fees
31 Aug - 1 Sept
Chapel Gate 3BR Steps to City Dock & Naval Academy
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and a water tower.

16. Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,687
HK$2,148 total
includes taxes & fees
31 Aug - 1 Sept
Sailboat Experience in Annapolis

17. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (6 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$1,510
HK$3,830 total
includes taxes & fees
31 Aug - 1 Sept
Pool Loft Suite | Bay Access & Beach Passes
A waterfront town with historic buildings, a dock with boats, and a prominent white dome structure in the background.

18. 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$1,501
HK$3,999 total
includes taxes & fees
30 Aug - 31 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

19. 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$2,441
HK$4,945 total
includes taxes & fees
1 Sept - 2 Sept
Mins to DTA - King Beds - Parking
A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

20. 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
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is HK$2,718
HK$6,176 total
includes taxes & fees
30 Aug - 31 Aug
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.
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

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"."
ROBERT 1-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Annapolis by IHG

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 Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! and Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

How many holiday rentals will I find in Annapolis?

Expedia has 378 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 The Colonial Players. 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.