Annapolis Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Rentals in Annapolis

Our top choices for Annapolis vacation rentals

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (31)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (76)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is CA $374
CA $686 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Oasis of Annapolis Star

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (229)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Private Cottage on gated estate

10.0 out of 10, Exceptional, (28)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (11)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is CA $1,149
CA $1,923 total
includes taxes & fees
Aug 25 - Aug 26
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (77)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (164)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

9.8 out of 10, Exceptional, (23)
"Great location, great host! "
The price is CA $397
CA $1,482 total
includes taxes & fees
Sep 2 - Sep 3
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock

Annapolis Home Near Beach & Quiet Waters Park!

Annapolis Home Near Beach & Quiet Waters Park!

Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (2)
"This tastefully decorated apartment is in a perfect location to enjoy all that is Annapolis. "
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (37)
"Great location"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (18)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is CA $624
CA $1,030 total
includes taxes & fees
Aug 24 - Aug 25
Secluded Cozy Cottage in Historic Downtown

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (39)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (23)
"Beautiful historic downtown location. Easy walk to everything. Cleane wonderful, it's historic building. And our host was absolutely it's terrific."
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (94)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Annapolis Hotel Reviews

Frequently asked questions

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Annapolis Maritime Museum, 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Annapolis vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Annapolis are Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! and Charming Historic Townhouse Steps From USNA.

How many vacation rentals will I find in Annapolis?

Expedia has 438 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Carrs Beach and Maryland Quiet Waters Park, or simply take in cultural attractions like Maryland Hall for Creative Arts 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.