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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Annapolis vacation rentals

Exterior

1. 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Eastport
10.0 out of 10, Exceptional, (146 reviews)
"Great location, charming decor, extra clean and well-provisioned."
United States
Pat D.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Terrace/patio

2. 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)
"In Annapolis for youth sports. Great place to stay. "
United States
jason S.
$479 nightly
The price is $546
Aug 29 - Aug 30
Total with taxes and fees
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Marina

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (84 reviews)
"Very clean and comfortable home conveniently located near Main St. Great communication as well make this a place I highly recommend!"
United States
Matt R.
$436 nightly
The price is $497
Aug 12 - Aug 13
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
Coffee/tea maker, fridge, microwave, oven

4. 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
Aug 11 - Aug 12
Total with taxes and fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Interior

5. 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, (1 review)
"Excellent place to stay!"
United States
Michaell M.
$654 nightly
The price is $716
Aug 11 - Aug 12
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.
Interior

6. 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.
$466 nightly
The price is $531
Aug 24 - Aug 25
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
Coffee/tea maker, fridge, microwave, oven

7. 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.
$648 nightly
The price is $733
Aug 12 - Aug 13
Total with taxes and fees
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Marina

8. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
$657 nightly
The price is $749
Aug 11 - Aug 12
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
Interior

9. 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.
$371 nightly
The price is $423
Aug 31 - Sep 1
Total with taxes and fees
New Downtown Annapolis Condo With Free Parking
Interior

10. 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.
$411 nightly
The price is $469
Aug 31 - Sep 1
Total with taxes and fees
Dean Street's Lower Deck House!
Exterior

11. 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, (54 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
$405 nightly
The price is $461
Aug 13 - Aug 14
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Exterior detail

12. 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.
$485 nightly
The price is $553
Aug 12 - Aug 13
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

13. 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.
$1,127 nightly
The price is $1,285
Aug 11 - Aug 12
Total with taxes and fees
Luxe Row Home Steps to USNA Gate 3!
Marina

14. 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
$425 nightly
The price is $485
Aug 11 - Aug 12
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Outdoor pool, a heated pool

15. 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
$392 nightly
The price is $447
Sep 1 - Sep 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

16. 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
Aug 16 - Aug 17
Total with taxes and fees
Eastport 3 bedroom Cottage: Walk to Downtown
Interior

17. Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great properties in a perfect location!"
United States
Pat K.
$784 nightly
The price is $894
Aug 12 - Aug 13
Total with taxes and fees
Two Historic Rowhomes in Downtown Annapolis
Coffee/tea maker, fridge, microwave, oven

18. 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.
$336 nightly
The price is $383
Aug 11 - Aug 12
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Coffee/tea maker, fridge, microwave, oven

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.
$526 nightly
The price is $600
Aug 31 - Sep 1
Total with taxes and fees
Mins to DTA - King Beds - Parking
Interior

20. 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.
$504 nightly
The price is $575
Aug 18 - Aug 19
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

10/10 Excellent
"Clean room, friendly staff close to restaurants"
SATANYA 2-night trip
Posted 1 hour ago
Hilton Garden Inn 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 $447 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 377 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 The Colonial Players. 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.