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Queen Anne Vacation Rentals

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Dec 15 - Dec 16
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Dec 16 - Dec 17
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Dec 19 - Dec 21
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Dec 26 - Dec 28

Our top choices for Queen Anne vacation rentals

Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
6.4 out of 10, (7)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Villa in Rock Hall

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Apartment in Downtown St. Michaels

Downtown St. Michaels | Porch + Pet-Friendly
Downtown St. Michaels | Porch + Pet-Friendly
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Vacation Home in Stevensville

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (16)
"The location was great! And clean beautiful house "
United States
Sarah S.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,425
￥24,749 total
includes taxes & fees
Dec 17 - Dec 18
First Floor Studio Apartment in Historic Chestertown
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Cabin in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (12)
"Great cabin and the dock is amazing. Family and dog had a lot of fun and it was convenient for visiting beaches and parks. "
United States
Marnie D.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥31,162
￥47,070 total
includes taxes & fees
Jan 1 - Jan 2, 2026
BAYSIDE BUNGALOW
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in Downtown St. Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (125)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Private kitchen
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Vacation Home in Chestertown

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
10.0 out of 10, Exceptional, (3)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Families

Vacation Home in stevensville

240' Private Beachfront @Kent Island Love Point - Great for Families
10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Families
Fridge, microwave, stovetop, dishwasher
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Vacation Home in Chester

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (126)
"Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly.."
United States
Karen K.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Interior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cottage in Stevensville

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Vacation Home in Downtown St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (46)
"Perfect location, everything as advertised. Highly recommend "
United States
Glen H.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Apartment in Downtown St. Michaels

Modern Flat in the Heart of St. Michaels – Walk Everywhere
9.8 out of 10, Exceptional, (57)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Property grounds
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Vacation Home in Grasonville

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Interior
200 steps to the beach!

Vacation Home in Rock Hall

200 steps to the beach!
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Terrace/patio
Waterfront Sunset Bayview: sleeps 6

Vacation Home in Chester

Waterfront Sunset Bayview: sleeps 6
10.0 out of 10, Exceptional, (24)
"Great open space for a relaxing family weekend. The property was very clean and the host was very responsive. Would love to stay again."
United States
Sonoka F.
Waterfront Sunset Bayview: sleeps 6
Exterior
Dollhouse in Central Historic St Michaels

Vacation Home in Downtown St. Michaels

Dollhouse in Central Historic St Michaels
9.8 out of 10, Exceptional, (56)
"We highly enjoyed our stay. It was a great location and we got a lot of use out of the screened in porch. The coffee shop out back was a great visit in the morning. "
United States
Nitarah I.
Dollhouse in Central Historic St Michaels
Property grounds
Stylish Home on the Choptank River (with Tidal Beach)

Vacation Home in Preston

Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, (44)
"Location was the best part of the stay. The access to the river was great."
United States
Teresa H.
Stylish Home on the Choptank River (with Tidal Beach)
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Room was clean The staff was excellent.we were greeted each morning with a smile when we came down for coffee. Great service from Sarah in the evening "
Teresa 2-night trip
Posted 1 day ago
Hilton Garden Inn Kent Island Marina

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:

  • View our selection of featured holiday rentals in Queen Anne
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  • Enter your travel dates to view the best deals on holiday rentals in Queen Anne while they last

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.