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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Annapolis vacation rentals

Exterior detail

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, (4 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
$514 nightly
The price is $586
Jul 21 - Jul 22
Total with taxes and fees
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Coffee/tea maker, fridge, microwave, oven

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)
"Very recent remodel, and all top notch. You can tell the owners put their heart and soul into this property. All the rooms have been very nicely done. Bathrooms were beautifully done. Beds were comfortable. The area is very peaceful and quiet. We really enjoyed the back yard space also. Sat at patio table and used grill. Large TV’s everywhere! We were able to sit at patio table, grill some burgers and watch Final Four games from TV in kitchen area. If you have a Midshipman, this property is...
United States
Brian S.
$1,127 nightly
The price is $1,285
Jul 22 - Jul 23
Total with taxes and fees
Luxe Row Home Steps to USNA Gate 3!
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$495 nightly
The price is $564
Jul 21 - Jul 22
Total with taxes and fees
Historic Row Home in Downtown Annapolis
Coffee/tea maker, fridge, microwave, oven

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.
$354 nightly
The price is $404
Jul 27 - Jul 28
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Interior

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.
$480 nightly
The price is $548
Aug 18 - Aug 19
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
Coffee/tea maker, fridge, microwave, oven

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.
$675 nightly
The price is $764
Jul 21 - Jul 22
Total with taxes and fees
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
$269 nightly
The price is $274
Jul 23 - Jul 24
Total with taxes and fees
Sailboat Experience in Annapolis
Coffee/tea maker, fridge, microwave, oven

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
$467 nightly
The price is $529
Jul 22 - Jul 23
Total with taxes and fees
Cute bungalow blocks to Stadium
Outdoor dining

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
$464 nightly
The price is $525
Aug 10 - Aug 11
Total with taxes and fees
Chapel Gate 3BR Steps to City Dock & Naval Academy
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (83 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
$442 nightly
The price is $503
Aug 11 - Aug 12
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
Coffee/tea maker, fridge, microwave, oven

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$438 nightly
The price is $499
Aug 1 - Aug 2
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Interior

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, (9 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.
$558 nightly
The price is $636
Jul 28 - Jul 29
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (84 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$434 nightly
The price is $495
Jul 21 - Jul 22
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Interior

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
$594 nightly
The price is $650
Jul 21 - Jul 22
Total with taxes and fees
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.
Coffee/tea maker, fridge, microwave, oven

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.
$675 nightly
The price is $770
Jul 20 - Jul 21
Total with taxes and fees
Eastport 3 bedroom Cottage: Walk to Downtown
Interior

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.
$485 nightly
The price is $553
Aug 18 - Aug 19
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
Exterior

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, (52 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
$434 nightly
The price is $494
Jul 20 - Jul 21
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Coffee/tea maker, fridge, microwave, oven

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.
$770 nightly
The price is $878
Jul 20 - Jul 21
Total with taxes and fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Coffee/tea maker, fridge, microwave, oven

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
$608 nightly
The price is $693
Jul 21 - Jul 22
Total with taxes and fees
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Coffee/tea maker, fridge, microwave, oven

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.
$505 nightly
The price is $576
Jul 28 - Jul 29
Total with taxes and fees
Mins to DTA - King Beds - 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The hotel staff and valet servers were very professional and friendly."
Mark 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

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 $495 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 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 vacation rentals will I find in Annapolis?

Expedia has 372 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Sandy Point Beach, or simply take in cultural attractions like Hammond-Harwood House and Annapolis Maritime Museum. 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.