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Queen Anne Vacation Rentals

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Mar 27 - Mar 29

Vacation Rentals in Queen Anne

Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Apartment in Saint Michaels

Downtown St. Michaels | Porch + Pet-Friendly
Marina
Floating 2 bed 2 bath condo stunning views of the bay

Houseboat in Stevensville

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
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Vacation Home in Stevensville

10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

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
Interior
200 steps to the beach!

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Villa in Rock Hall

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
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Vacation Home in St. Michaels

9.8 out of 10, Exceptional, (45)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Vacation Home in stevensville

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 Large Groups
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in Saint Michaels

9.6 out of 10, Exceptional, (124)
"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!
Property grounds
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Vacation Home in Grasonville

10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$255 nightly
The price is $270
Jan 4 - Jan 5, 2026
Total with taxes and fees
BAYSIDE BUNGALOW
Fridge, microwave, stovetop, dishwasher
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Vacation Home in Chester

10.0 out of 10, Exceptional, (126)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
United States
Sue R.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 8 - Dec 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in 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.
$240 nightly
The price is $254
Dec 11 - Dec 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, oven, stovetop
Waterfront! Private Dock, Boat Tie-Up & Near Town

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town
Dining
Cass-Away Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (104)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
$257 nightly
The price is $284
Dec 6 - Dec 7
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Vacation Home in Chestertown

10.0 out of 10, Exceptional, (76)
"Great house, will stay again in the future. "
United States
Gary N.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Cabin in Chestertown

10.0 out of 10, Exceptional, (12)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior
Dollhouse in Central Historic St Michaels

Vacation Home in 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
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 great! In room tub was a bit smaller than I was expecting but still quite adequate! View from room was very nice."
Madeline 1-night trip
Posted 3 days ago
Hilton Garden Inn Kent Island Marina

Find out more about Queen Anne

Everything you need to know about Queen Anne vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Queen Anne vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Queen Anne vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Queen Anne vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Queen Anne. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Queen Anne in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Queen Anne rentals

At Expedia, we put the best Queen Anne vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Queen Anne rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Queen Anne vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Queen Anne. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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. : You might like this vacation home rental near Queen Anne. It 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 Hazel Miner Monument, or get out into nature at a spot like Chesapeake Bay Environmental Center. In the larger area, you’ll find Tuckahoe State Park and Queenstown Premium Outlets.

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.