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

Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Annapolis vacation rentals

A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

1. 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 ￥32,309
￥84,398 total
includes taxes & fees
Oct 5 - Oct 6
Upscale Condo in Annapolis w/Private Parking
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

2. 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 ￥32,009
￥77,558 total
includes taxes & fees
Sep 27 - Sep 28
Dean Street's Lower Deck House!

3. 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 ￥40,534
￥92,699 total
includes taxes & fees
Sep 28 - Sep 29
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A wooden dock extending into a calm body of water with boats docked at the end.

4. 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 ￥33,822
￥67,968 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 2br home w/ parking in downtown Annapolis
A living room with a dining table, two sofas, a coffee table, and a patterned rug.

5. 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 ￥32,120
￥81,751 total
includes taxes & fees
Sep 24 - Sep 25
Chapel Gate 3BR Steps to City Dock & Naval Academy
A kitchen with a wooden countertop, a stove, and a refrigerator.

6. 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 ￥36,669
￥66,910 total
includes taxes & fees
Sep 24 - Sep 25
18th Cent. Charm in Historic Downtown Annapolis
A bedroom with a sloped ceiling, a bed with a striped bedspread, two red chairs, a television mounted on the wall, and a window with blinds.

7. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
The price is ￥28,813
￥98,988 total
includes taxes & fees
Sep 24 - Sep 25
Annapolis Charmer - Perfect Location

8. 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)
The price is ￥30,230
￥88,310 total
includes taxes & fees
Sep 28 - Sep 29
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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 ￥41,215
￥114,248 total
includes taxes & fees
Sep 28 - Sep 29
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A house with a red door, a small porch, and a view of a river with a bridge in the background.

10. 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, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is ￥30,876
￥48,994 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

11. 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 ￥30,073
￥197,083 total
includes taxes & fees
Sep 24 - Sep 25
Luxe Row Home Steps to USNA Gate 3!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

12. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
"This property was an up and down property for us. The ups: check in process was flawless; cleanliness was as good as an old house can be; and the location was superb. The downs: they say it can sleep ten. Well ten people might sleep but they can’t do much else. There are two baths and the kitchen was fine and although adequate to work with. But there are only four wine glasses and barely five people can sit at the dining room table. So if ten people sleep - they wake up and there are enough...
United States
DEAN F.
The price is ￥29,286
￥88,849 total
includes taxes & fees
Sep 24 - Sep 25
Historic Row Home in Downtown Annapolis
A modern kitchen with a central island, built-in oven, and microwave.

13. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (12 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 ￥32,592
￥82,897 total
includes taxes & fees
Sep 28 - Sep 29
Cute bungalow blocks to Stadium
A modern kitchen with a central island, stainless steel range hood, and a built-in oven.

14. Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
The price is ￥47,193
￥91,101 total
includes taxes & fees
Sep 27 - Sep 28
Walk to the stadium! - Lighthouse on Glenwood
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

15. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (1 review)
"We had a nice stay. All was fine."
United States
william c.
The price is ￥49,123
￥123,430 total
includes taxes & fees
Sep 28 - Sep 29
Eastport 3 bedroom Cottage: Walk to Downtown

16. 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 ￥32,878
￥79,086 total
includes taxes & fees
Sep 29 - Sep 30
Pool Loft Suite | Bay Access & Beach Passes
A beach with chairs and a pier in the background.

17. 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, (19 reviews)
"Almost everything that you might need is provided, but if not there is shopping close by. Hot tub was nice. Very clean home."
United States
Sharon Z.
The price is ￥34,718
￥80,144 total
includes taxes & fees
Sep 28 - Sep 29
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A multi-story residential building with solar panels on the roof, a front porch, and a well-maintained garden.

18. Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
10.0 out of 10, Exceptional, (3 reviews)
"Communication and check-in process was great. Host made himself available in case we had any concerns or questions. Great location easy to get to downtown and to the outskirts. Wonderful to have the driveway with parking."
United States
D R.
The price is ￥58,450
￥104,830 total
includes taxes & fees
Oct 20 - Oct 21
Adorable home steps from Navy stadium!
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

19. 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 ￥31,333
￥88,849 total
includes taxes & fees
Oct 20 - Oct 21
Annapolis Retreat - 7 mins from downtown Annapolis!
A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

20. Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is ￥38,796
￥100,587 total
includes taxes & fees
Sep 27 - Sep 28
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Very nice decor and bed was comfortable . Classy looking place ."
princess 2-night trip
Posted 17 hours ago
Graduate by Hilton 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 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 382 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.