House vacation rentals in Queen Anne's County

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Popular amenities for Queen Anne's County house rentals

House rentals with a pool

Top guest favourite
Home in Chestertown
5 out of 5 average rating, 22 reviews

Chestertown Watson Family Farm

TaraRating, 5 stars6 months ago
We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.
Guest favourite
Home in Rock Hall
4.94 out of 5 average rating, 36 reviews

Rockfish Keeper

Kore MichaelRating, 5 stars4 months ago
The house was exactly as described and it was so easy to communicate with them as they responded to texts within minutes
Guest favourite
Home in Denton
4.96 out of 5 average rating, 23 reviews

*NEW* The Wilder Way

KarynRating, 5 stars2 months ago
We stayed in January 2025 for a family gathering with 6 adults and 6 kids (ages 5 months to 8 years). The house is lovely and we enjoyed cooking in the beautiful kitchen and sitting by the fireplace. Although the yard and play structure were covered in snow, the kids enjoyed it all anyway including roller skating and scootering on the long driveway. Our host was very responsive to a few issues we encountered. Something to know about the bunk room--you must go through the garage to get to it. It was fine for our purposes. The beds and linens were all very comfortable. The shower and bath in the primary bedroom was a treat.
Top guest favourite
Home in Rock Hall
5 out of 5 average rating, 12 reviews

The Mariner's House

VivianRating, 5 stars3 days ago
We thoroughly enjoyed our stay. The location was perfect. The Bay was across the street. There were many extra Amenities available to us on the grounds. The house was in a perfect location, very well maintained, fully equipped, very cozy, and within walking distance to everything. The neighborhood was quiet and peaceful. Megan was the perfect host. She was very welcoming, friendly, warm, and responsive. Everything went smoothly and was exactly how she said that it would be. There were no unexpected surprises. We can't wait to go back!
Top guest favourite
Home in Chester
4.99 out of 5 average rating, 90 reviews

Waterfront Farmhouse Meets Modern Luxury

JayRating, 5 stars1 week ago
We had a wondferful time with extended family at this beautiful spot where you're surrounded by nature and expansive views from inside and outside the house. The views of the water and sunsets are breathtaking. The house has everything needed to cook family meals and share a comfortable and revitalizing time.
Top guest favourite
Home in Centreville
4.98 out of 5 average rating, 55 reviews

The Colonial Farmhouse

SarahRating, 5 stars7 months ago
We had a great stay! It was the perfect meeting point for three families who live in and down the East Coast. There was plenty of space to accommodate us all. The home was beautiful - it’s clear the owners put their blood, sweat and tears into a renovation that really paid off. Great place to stay with children. Highly recommend!
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 29 reviews

Wildbluesea Retreat

TerriRating, 5 stars5 months ago
We came to the area for a wedding and had 8 adults and 2 children. There was plenty of room and everything was very clean and welcoming. There was a large table for all of us to fit at and eat together and we especially enjoyed our time in the hot tub. Janean was very quick to respond and gave us great recommendations for dinner. The area was beautiful and we would definitely love to come back some time in the future and stay at the Wildbluesea Retreat!
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 15 reviews

Bayside Escape

StacyRating, 5 stars5 months ago
Our family loved our too-short stay at Jessica’s lovely home. Mornings looking out on the water and lounging on the outdoor deck were so tranquil. The home has a wonderful orientation and light-filled living area. Plenty of space, well laid-out and just about every convenience one needs in this comfortable abode!

Weekly house rentals

Superhost
Home in Chestertown
4.76 out of 5 average rating, 17 reviews

Langford Creek | Waterfront w/ HOT TUB + Fire Pit!

KristinRating, 5 stars6 months ago
I recently stayed at this vacation rental, and I couldn’t be more pleased with the experience. The accommodations were absolutely beautiful and incredibly spacious, providing plenty of room to relax and enjoy the surroundings. Each room was generously sized, offering comfort and an open, airy feel that added to the overall relaxation. Cleanliness was top-notch; everything was spotless when we arrived, which made us feel immediately at ease. The amenities were also great—everything we needed for a comfortable stay was provided, from a well-equipped kitchen to fast Wi-Fi and plenty of towels and linens. The location was perfect, offering both tranquility and easy access to nearby attractions. We were close enough to explore local shops and restaurants, yet far enough to enjoy peace and quiet when we wanted it. The host provided clear and detailed directions, making check-in and navigating the area completely hassle-free. Overall, I highly recommend this rental.
Guest favourite
Home in Stevensville
4.91 out of 5 average rating, 77 reviews

Cheerful & Spacious Shore Life Beauty!

TrishRating, 5 stars4 months ago
Excellent stay and wonderful property. Many thanks!
Guest favourite
Home in Chestertown
4.93 out of 5 average rating, 41 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

ErickRating, 5 stars3 months ago
The location was super beautiful overlooking the Chester River like the opening scenes from the Dead Poet Society, which was filmed not too far away. We really enjoyed the facility and land, river as it provided a wintry rustic feel. I loved the hickory smokiness smell of the open fireplaces upon walking in. On the side, my wife not as much since she had to dry clean some items. Ina was amazingly responsive on all our questions and requests, even on her birthday! She even had needed house supplies delivered while we were there. This made our stay so much more comfortable. It was a wonderful stay, even though it was raining much of our time. A great rainy day stay location!
Superhost
Home in Queenstown
4.97 out of 5 average rating, 35 reviews

Unwind on the Wye River

AmandaRating, 5 stars4 months ago
beautiful spacious home. great for my family of 6 to meet up with our USNA midshipmen. loved the back yard and living rooms
Superhost
Home in Centreville
5 out of 5 average rating, 4 reviews

Your Dream Stay: Luxury Kitchen, Hot Tub & Firepit

CharlesRating, 5 stars3 months ago
We had the pleasure of staying in this charming and inviting home for Christmas. The home was spacious and comfortable for us. The house was beautifully decorated and cozy by the fireplace. The hot tub and firepit were great spots for relaxing in the evenings. Such a wonderful spot for a peaceful and comfortable retreat. The location is also great within a short drive to a nice coffee shop and great shops. Tammy was also a great host!
Top guest favourite
Home in Chestertown
5 out of 5 average rating, 35 reviews

In Town Chestertown Rancher (1 Block to College)

ColleenRating, 5 stars4 days ago
This was a perfect home for a 60th celebration. The home was spotless, beds so comfortable, kitchen well appointed. Host left touches for guests to feel comfortable and welcomed. Quiet neighborhood, great backyard and close enough to walk to stores, resturants and Washington College. I would highly recommend this home for a familiy or friends get away.
Top guest favourite
Home in Annapolis
4.98 out of 5 average rating, 99 reviews

Hot Tub Haven: Annapolis Backyard Oasis!

JenniRating, 5 stars2 months ago
We had a great time at Justin's place! We were 2 families with 5 small kids getting out of DC for the holiday weekend, and Justin's place gave us just what we needed. The kids had a great time playing in the downstairs playroom, making snowmen in the big backyard, playing with the puzzles and games, and walking across the street to see the frozen water. The house had everything we needed, and we hope to go back in warmer weather to take advantage of the beach access! Justin was a fantastic host - super communicative, responsive and understanding (like I said, 5 small kids :) - he even came to the house late the first night to drop off extra crib sheets for the pack and play! And the location was great - a quiet street, near the water, but also super close to a shopping center that had everything we needed (grocery store, pizza shop, liquor store), and just 15 minutes to all the places we wanted to go. We had a great time!
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 31 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

TammyRating, 5 stars2 months ago
Oh my goodness! This home was perfect for our ladies retreat! We felt at home! And the views were breathtaking! We loved our stay in this gorgeous home! ! We will definitely be back again!

Private house rentals

Guest favourite
Home in Rock Hall
5 out of 5 average rating, 12 reviews

Bay Beach Oasis

JamesRating, 5 stars5 months ago
Curtis was a wonderful host -- super responsive when we had questions, made certain we arrived safely and securely, had the house spotless on arrival and really took care to make us as comfortable as possible. Sleeping was a dream -- new mattresses and the freshest linens. Rock Hall is lovely, quiet bayside town for a real getaway, and an easy drive to other spots on the Eastern Shore.
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 6 reviews

Sleeps12*MainHouse+DetachedApt*Wedding Venues&USNA

LauraRating, 5 stars5 months ago
Karin and Andrew’s place was wonderful! The pictures represented the home perfectly. We were in town for our son’s wedding and 8 people comfortably stayed in the main house and then we had 2 more in the garage apartment. Both the house and garage apartment were clean and clutter free, everything is labeled and easily found, along with a binder full of instructions and recommendations. Karin left us a welcome to their home message that was personalized for our visit. We stayed on Halloween and a bowl of candy was left for us in case we had any trick or treaters. The house is easy to find and access. Karin was proactive in messaging me and quick to respond to any inquiries. Our family enjoyed our stay and all would highly recommend this home.
Top guest favourite
Home in Grasonville
5 out of 5 average rating, 47 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

MichaelRating, 5 stars1 week ago
Great place to stay - we had a quick work trip and it worked out great. Very clean and neat.
Top guest favourite
Home in Rock Hall
5 out of 5 average rating, 29 reviews

1-Particular Harbor: A Coastal Oasis!

EmmaRating, 5 stars4 months ago
Gregory’s place was spectacular! And he is the most responsive and helpful AirBnB host I’ve ever had, and he is just so kind! The house was clean, beautifully decorated, had so many amenities, and just had so many thoughtful touches. It’s in a great location too. We cannot wait to come back to visit 1PH and Rock Hall!! Thank you Gregory!!
Top guest favourite
Home in Chestertown
5 out of 5 average rating, 37 reviews

Magnolia House: walk to shops, restaurants, river

NancyRating, 5 stars1 month ago
Hannah was very accommodating with our arrival and departure. Lots of thoughtful and generous amenities. Bed was extremely comfortable and the bed linens crisp and white. Towels were plentiful. The house was very comfortable and we felt right at home. The location is ideal. Quiet and yet conveniently close to the central shopping district. We look forward to visiting again.
Guest favourite
Home in Denton
4.9 out of 5 average rating, 87 reviews

Historic 19th Century Eastern Shore Farmhouse

PaulRating, 5 stars4 months ago
This historic property in Maryland is an amazing find. The property is a lovely two plus acres with many cozy retreats to stop and take in the wonderful trees. If you want a more rigorous outdoor experience, there is a lovely park 5 minutes away and a larger area with an arboretum about 15 minutes away. It is an easy walk into downtown which has several restaurants. The hosts have thought of everything, and I do mean everything. The character of the house is exceptional, but it is comfortable not stuffy. Lots of amazing artwork and books throughout. The kitchen is fully stocked and comfortable to eat or cook in. The rain shower in the bathroom was delightful and the beds are comfortable. It was a perfect place to have a mini family reunion for a few days. We will be visiting the house again
Superhost
Home in Chester
4.75 out of 5 average rating, 8 reviews

Crab Alley Bay House, Waterfront Home w Hot Tub

StephanieRating, 5 stars5 months ago
Kathryn's place was clean and beautiful! Kathyrn provided many thoughtful amenities such as sound machines, night lights, and coffee for the coffee maker. The house has a great set up, especially if you are looking for somewhere fun to spend a holiday! The kitchen would be great for a lot of cooking, and the beautiful dining room table has enough room for a lot of guests. We truly enjoyed our stay and hope to be back!
Guest favourite
Home in Annapolis
4.9 out of 5 average rating, 198 reviews

Country House on the Bay

ChristinaRating, 5 stars5 months ago
This house was perfect for our family—wonderful location, big and beautiful outdoor space, all of the amenities our family needed during our stay. Steve is a wonderful host—kind, excellent communicator, and highly responsive. Ten out of ten experience!

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