Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

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 $403
CA $968 total
includes taxes & fees
Jul 20 - Jul 21
Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is CA $374
CA $1,021 total
includes taxes & fees
Jun 26 - Jun 27
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $545
CA $1,033 total
includes taxes & fees
Jul 14 - Jul 15
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 $623
CA $1,134 total
includes taxes & fees
Jul 1 - Jul 2
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
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 $541
CA $979 total
includes taxes & fees
Jun 28 - Jun 29
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 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 $611
CA $1,145 total
includes taxes & fees
Jun 30 - Jul 1
Charming Annapolis WaterVIEW Home

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, (5 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is CA $588
CA $860 total
includes taxes & fees
Jul 6 - Jul 7
Fabulous 5-bedroom house with AC in charming Annapolis

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is CA $305
CA $386 total
includes taxes & fees
Jun 24 - Jun 25
Sailboat Experience in Annapolis

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (9 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is CA $297
CA $760 total
includes taxes & fees
Jul 1 - Jul 2
Cute bungalow blocks to Stadium

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 $425
CA $757 total
includes taxes & fees
Jul 15 - Jul 16
Waterfront Oasis of Annapolis Star

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is CA $306
CA $762 total
includes taxes & fees
Jul 1 - Jul 2
Chapel Gate 3BR Steps to City Dock & Naval Academy

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is CA $310
CA $865 total
includes taxes & fees
Jul 1 - Jul 2
Historic Row Home in Downtown Annapolis

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 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 $637
CA $1,060 total
includes taxes & fees
Jun 26 - Jun 27
Secluded Cozy Cottage in Historic Downtown

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.8 out of 10, Exceptional, (7 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 $395
CA $965 total
includes taxes & fees
Jul 1 - Jul 2
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is CA $628
CA $1,003 total
includes taxes & fees
Jul 13 - Jul 14
Adorable home steps from Navy stadium!

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
The price is CA $548
CA $1,358 total
includes taxes & fees
Jun 26 - Jun 27
Two Historic Rowhomes in Downtown Annapolis

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"The house was well equipped, clean and comfortable. The host was very accommodating and responsive. This is a great home if you have a large crowd and so convenient to historic Annapolis. "
United States
Susan R.
The price is CA $1,354
CA $2,409 total
includes taxes & fees
Jul 21 - Jul 22
Historic Annapolis Charmer <1Mile to NMC Stadium

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (4 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 $304
CA $894 total
includes taxes & fees
Jul 1 - Jul 2
Luxe Row Home Steps to USNA Gate 3!

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, (3 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is CA $639
CA $1,202 total
includes taxes & fees
Jun 27 - Jun 28
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

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)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
The price is CA $541
CA $703 total
includes taxes & fees
Jun 27 - Jun 28
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

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 Annapolis WaterVIEW Home: Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach.

How many vacation rentals will I find in Annapolis?

Expedia has 380 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 Annapolis Maritime Museum and Hammond-Harwood House. 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.