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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Annapolis vacation 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.
$423 nightly
The price is $482
Nov 2 - Nov 3
Total with taxes and fees
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
$558 nightly
The price is $631
Oct 13 - Oct 14
Total with taxes and fees
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.
$373 nightly
The price is $425
Oct 13 - Oct 14
Total with taxes and fees
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.
$1,106 nightly
The price is $1,261
Oct 20 - Oct 21
Total with taxes and fees
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.
$506 nightly
The price is $577
Oct 20 - Oct 21
Total with taxes and fees
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.
$498 nightly
The price is $568
Oct 20 - Oct 21
Total with taxes and fees
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.
$451 nightly
The price is $510
Nov 4 - Nov 5
Total with taxes and fees
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.
$454 nightly
The price is $518
Oct 18 - Oct 19
Total with taxes and fees
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.
$471 nightly
The price is $533
Oct 19 - Oct 20
Total with taxes and fees
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
$423 nightly
The price is $482
Nov 1 - Nov 2
Total with taxes and fees
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.
$417 nightly
The price is $475
Nov 9 - Nov 10
Total with taxes and fees
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, (1 review)
"We had a nice stay. All was fine."
United States
william c.
$750 nightly
The price is $854
Oct 20 - Oct 21
Total with taxes and fees
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.
$852 nightly
The price is $972
Oct 20 - Oct 21
Total with taxes and fees
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.
$670 nightly
The price is $758
Oct 12 - Oct 13
Total with taxes and fees
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.
$574 nightly
The price is $654
Oct 20 - Oct 21
Total with taxes and fees
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.
$444 nightly
The price is $506
Oct 13 - Oct 14
Total with taxes and fees
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.
$438 nightly
The price is $499
Oct 19 - Oct 20
Total with taxes and fees
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.
$440 nightly
The price is $502
Nov 2 - Nov 3
Total with taxes and fees
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.
$385 nightly
The price is $432
Nov 5 - Nov 6
Total with taxes and fees
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.
$592 nightly
The price is $675
Oct 20 - Oct 21
Total with taxes and fees
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
"Pool was out of order."
Greg 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Annapolis

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $425 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.