Photo by KM Moore

Queen Anne Vacation Rentals

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Our top choices for Queen Anne vacation rentals

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ¥10,541
¥19,389 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Guest Suite for up to 2 in a Victorian on the Chester River

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is ¥11,719
¥39,863 total
includes taxes & fees
Dec 21 - Dec 22
Charming Coastal/Country Home w/3 Acres & Sauna!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is ¥14,900
¥43,399 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is ¥15,346
¥24,622 total
includes taxes & fees
Dec 18 - Dec 19
First Floor Studio Apartment in Historic Chestertown

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ¥55,804
¥94,479 total
includes taxes & fees
Dec 29 - Dec 30
Turnbridge Manor

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is ¥33,947
¥73,118 total
includes taxes & fees
Jan 5 - Jan 6, 2026
HGTV quality, private guest suite, country getaway with hot tub & fire pit

New! Stylish downtown home w/awesome outdoor area!

New! Stylish downtown home w/awesome outdoor area!
Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is ¥34,180
¥77,966 total
includes taxes & fees
Dec 25 - Dec 26
New! Stylish downtown home w/awesome outdoor area!

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is ¥61,849
¥137,195 total
includes taxes & fees
Dec 19 - Dec 20
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥31,002
¥46,829 total
includes taxes & fees
Jan 1 - Jan 2, 2026
BAYSIDE BUNGALOW

Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is ¥34,877
¥42,228 total
includes taxes & fees
Dec 18 - Dec 19
Chesapeake Bay Harbor View in a central location to events/restaurants

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is ¥38,753
¥64,575 total
includes taxes & fees
Dec 18 - Dec 19
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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 Queen Anne Hotel Reviews

Find out more about Queen Anne

Search for holiday rentals in Queen Anne on Expedia! You can easily find your home rentals, villas, holiday apartments in Queen Anne using one of the methods below:

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Look no further and take a look at our great range of rental properties in Queen Anne!

Frequently asked questions

Can I find vacation rentals in Queen Anne?

Yes, you can find vacation rentals near top local attractions in Queen Anne, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Queen Anne has to offer?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This vacation home near Queen Anne is located on a river and has a patio, 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 fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

What can I see and do in Queen Anne?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Chesapeake Bay Environmental Center. In the larger area, you’ll find Tuckahoe State Park and Wye Landing.

What are vacation rentals like in Queen Anne?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Queen Anne. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.