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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Annapolis vacation rentals

1. 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, (5 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A kitchen with a wooden countertop, a stove, and a refrigerator.

2. 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 CA $324
CA $591 total
includes taxes & fees
Aug 31 - Sep 1
18th Cent. Charm in Historic Downtown Annapolis
A kitchen counter with a marble top, a striped basket, a tissue box, and a potted plant.

3. 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 CA $283
CA $621 total
includes taxes & fees
Aug 31 - Sep 1
Dean Street's Lower Deck House!
A lobby with a reception desk, a blue sofa, a plant, and a door leading outside.

4. 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.
The price is CA $263
CA $585 total
includes taxes & fees
Aug 31 - Sep 1
New Downtown Annapolis Condo With Free Parking
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

5. 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 CA $363
CA $834 total
includes taxes & fees
Sep 29 - Sep 30
Upscale Condo in Annapolis w/Private Parking
A wooden dock extending into a calm body of water with boats docked at the end.

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

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (85 reviews)
"Thank you for the stay! We loved the location."
United States
Mary G.
The price is CA $318
CA $628 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 2br home w/ parking in downtown Annapolis
A swimming pool with a waterfall feature surrounded by lush greenery.

7. 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
The price is CA $307
CA $597 total
includes taxes & fees
Sep 1 - Sep 2
Waterfront Oasis of Annapolis Star
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

8. 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 CA $243
CA $1,712 total
includes taxes & fees
Aug 31 - Sep 1
Luxe Row Home Steps to USNA Gate 3!
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 CA $364
CA $1,010 total
includes taxes & fees
Aug 31 - Sep 1
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

10. 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.
The price is CA $267
CA $786 total
includes taxes & fees
Aug 31 - Sep 1
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.

11. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is CA $259
CA $786 total
includes taxes & fees
Aug 31 - Sep 1
Historic Row Home in Downtown Annapolis
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

12. 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.
The price is CA $435
CA $701 total
includes taxes & fees
Sep 17 - Sep 18
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with a central island, stainless steel range hood, and a built-in oven.

13. Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
The price is CA $417
CA $812 total
includes taxes & fees
Sep 27 - Sep 28
Walk to the stadium! - Lighthouse on Glenwood
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
9.8 out of 10, Exceptional, (10 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 CA $288
CA $738 total
includes taxes & fees
Aug 31 - Sep 1
Cute bungalow blocks to Stadium
A patio with a round table and chairs, a grill, and a wooden fence.

15. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is CA $284
CA $724 total
includes taxes & fees
Aug 31 - Sep 1
Chapel Gate 3BR Steps to City Dock & Naval Academy
An aerial view of a marina with numerous boats docked, surrounded by residential buildings and a water tower.

16. Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is CA $299
CA $378 total
includes taxes & fees
Aug 31 - Sep 1
Sailboat Experience in Annapolis

17. 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 CA $268
CA $676 total
includes taxes & fees
Aug 31 - Sep 1
Pool Loft Suite | Bay Access & Beach Passes
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
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
The price is CA $266
CA $706 total
includes taxes & fees
Aug 31 - Sep 1
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

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.
The price is CA $454
CA $909 total
includes taxes & fees
Aug 31 - Sep 1
Mins to DTA - King Beds - Parking
A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

20. 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, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is CA $482
CA $1,096 total
includes taxes & fees
Aug 31 - Sep 1
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.
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"We spent a week here and had a great stay. The kids really enjoyed the pool, and the location was ideal, with easy access to both D.C. and the ocean. Everything was great!"
Levente 7-night trip
Posted 9 hours ago
SpringHill Suites by Marriott Annapolis

Find out more about Annapolis

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Annapolis. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : Visitors like this Annapolis vacation home rental. It is located in the city center and has a fireplace, a patio, 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. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Private Cottage on gated estate.

How many vacation rentals will I find in Annapolis?

Expedia has 379 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.