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

Annapolis Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Annapolis vacation rentals

A white building with black shutters, a wooden door, and a number '53' on the wall.

1. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (16 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
The price is AED 856
AED 1,483 total
includes taxes & fees
14 Nov - 15 Nov
18th Cent. Charm in Historic Downtown Annapolis
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is AED 790
AED 1,600 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 2br home w/ parking in downtown Annapolis
A sign for "The Newport" with a house number 316, surrounded by well-maintained landscaping and a large tree.

3. Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!

Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is AED 758
AED 1,982 total
includes taxes & fees
15 Nov - 16 Nov
Luxe downtown Annapolis condo! On the harbor, rooftop views, cozy fireplace, memory foam beds, free parking & fully stocked home. Walk to shops, dining, USNA!
Exterior detail

4. 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, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AED 840
AED 1,946 total
includes taxes & fees
17 Nov - 18 Nov
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A modern lobby with a blue sofa, a plant, and a door leading outside.

5. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
Upscale Condo in Annapolis w/Private Parking
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

6. 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 AED 887
AED 1,826 total
includes taxes & fees
14 Dec - 15 Dec
Dean Street's Lower Deck House!
A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

7. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
Annapolis Charmer - Perfect Location
A living room with a dining table, two sofas, a coffee table, and a patterned rug.

8. 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.
Chapel Gate 3BR Steps to City Dock & Naval Academy
A two-story building with a balcony, a patio with outdoor furniture, and a wooden fence.

9. Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (8 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
Luxe Row Home Steps to USNA Gate 3!
A compact kitchen with a refrigerator, microwave, sink, and wooden cabinets.

10. Historic 2BR + Loft Home in Downtown Annapolis

Historic 2BR + Loft Home in Downtown Annapolis
Historic District
Historic 2BR + Loft Home in Downtown Annapolis
A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

11. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 AED 707
AED 1,694 total
includes taxes & fees
14 Nov - 15 Nov
Pool Loft Suite | Bay Access & Beach Passes
A hallway with a dark wooden door, a small table with a vase, wicker baskets, and a mirror on the wall.

12. 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)
"Great property!"
United States
Michael Z.
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.

13. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.4 out of 10, Exceptional, (3 reviews)
"Great little house on a perfect location"
United States
Amy T.
Historic Row Home in Downtown Annapolis
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
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
Cute bungalow blocks to Stadium
A white door with a glass panel, a window with blinds, a wicker chair, a small table, and a standing fan.

15. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great property. Big back yard. Nice walk to downtown and campus."
United States
Stephen P.
The price is AED 1,315
AED 2,923 total
includes taxes & fees
14 Dec - 15 Dec
Eastport 3 bedroom Cottage: Walk to Downtown
A two-story house with a porch, a wooden door, and a stone wall in front.

16. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Good location."
United States
Rosie G.
The price is AED 949
AED 2,938 total
includes taxes & fees
15 Nov - 16 Nov
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

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

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (11 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
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
9.0 out of 10, Wonderful, (4 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AED 826
AED 1,935 total
includes taxes & fees
15 Nov - 16 Nov
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with white cabinets, a black dishwasher, a stainless steel oven, and a ceiling fan.

19. 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 AED 1,309
AED 2,137 total
includes taxes & fees
16 Nov - 17 Nov
Adorable home steps from Navy stadium!
A house with a stone facade, a white door with a glass panel, and a porch with two potted plants.

20. 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 AED 771
AED 1,951 total
includes taxes & fees
30 Nov - 1 Dec
Annapolis Retreat - 7 mins from downtown Annapolis!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"1"
David Louis 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Maryland Hall for Creative Arts, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Annapolis vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. 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 vacation rentals will I find in Annapolis?

Expedia has 381 vacation 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 vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.