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

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
The price is CA $400
CA $723 total
includes taxes & fees
Jul 20 - Jul 21
Waterfront Oasis of Annapolis Star
Beach nearby, sun loungers, beach towels

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $524
CA $1,003 total
includes taxes & fees
Jul 22 - Jul 23
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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.
The price is CA $316
CA $852 total
includes taxes & fees
Aug 11 - Aug 12
Annapolis Retreat - 7 mins from downtown Annapolis!
Property grounds

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (14 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is CA $538
CA $985 total
includes taxes & fees
Jul 19 - Jul 20
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Smart TV, fireplace, foosball, table tennis

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is CA $556
CA $1,045 total
includes taxes & fees
Jul 22 - Jul 23
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is CA $302
CA $385 total
includes taxes & fees
Jul 23 - Jul 24
Sailboat Experience in Annapolis
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.4 out of 10, Very good, (6 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is CA $553
CA $812 total
includes taxes & fees
Jul 20 - Jul 21
Fabulous 5-bedroom house with AC in charming Annapolis
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is CA $674
CA $1,223 total
includes taxes & fees
Jul 22 - Jul 23
Charming Annapolis WaterVIEW Home
Fridge, microwave, oven, stovetop

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.
The price is CA $291
CA $749 total
includes taxes & fees
Jul 22 - Jul 23
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop

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 $435
CA $1,107 total
includes taxes & fees
Jul 22 - Jul 23
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is CA $270
CA $809 total
includes taxes & fees
Jul 21 - Jul 22
Historic Row Home in Downtown Annapolis
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is CA $346
CA $899 total
includes taxes & fees
Aug 16 - Aug 17
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Outdoor dining

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is CA $304
CA $757 total
includes taxes & fees
Jul 20 - Jul 21
Chapel Gate 3BR Steps to City Dock & Naval Academy
Fridge, microwave, oven, stovetop

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
The price is CA $340
CA $973 total
includes taxes & fees
Jul 22 - Jul 23
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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, (6 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.
The price is CA $303
CA $1,804 total
includes taxes & fees
Jul 22 - Jul 23
Luxe Row Home Steps to USNA Gate 3!
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.
The price is CA $380
CA $861 total
includes taxes & fees
Jul 20 - Jul 21
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
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.
The price is CA $293
CA $706 total
includes taxes & fees
Aug 2 - Aug 3
Pool Loft Suite | Bay Access & Beach Passes
Marina

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.
The price is CA $632
CA $1,052 total
includes taxes & fees
Jul 17 - Jul 18
Secluded Cozy Cottage in Historic Downtown
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is CA $544
CA $892 total
includes taxes & fees
Jul 20 - Jul 21
Adorable home steps from Navy stadium!
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.
The price is CA $537
CA $700 total
includes taxes & fees
Jul 20 - Jul 21
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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
"I loved the historic building- upgraded with 21stC amenities of course- like electricity and an elevator. Bed was very cozy. Bathroom window faced St. Mary's church and bedroom faced Capitol bldg. A short 2 block walk to a city owned parking garage, $24 for 24 hours. Not bad. And the restaurants all close by. I've been to Annapolis many times, but never overnight, so this was a great spot that my Lady absolutely adored!"
Frederick 1-night trip
Posted 10 hours ago
Historic Inns of 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?

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.