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 favorite
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 favorite
Home in Rock Hall
4.94 out of 5 average rating, 36 reviews

Rockfish Keeper

Kore MichaelRating, 5 stars5 months ago
The house was exactly as described and it was so easy to communicate with them as they responded to texts within minutes
Top guest favorite
Home in Rock Hall
5 out of 5 average rating, 13 reviews

The Mariner's House

VivianRating, 5 stars3 weeks 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 favorite
Home in Chester
4.99 out of 5 average rating, 90 reviews

Waterfront Farmhouse Meets Modern Luxury

JayRating, 5 stars4 weeks 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.
Superhost
Home in Saint Michaels
4.5 out of 5 average rating, 10 reviews

10 Minutes to St. Michaels with a Private Pool

JoyRating, 5 stars4 months ago
We had a great weekend a gain. Enjoying Christmas in St Michaels. Your home is beautiful. We ate at Ava’s, Limoncello, Carpenters and Talbots. Shopped on Sunday. Highly recommend the house tour. She you again soon.🥰
Top guest favorite
Home in Stevensville
5 out of 5 average rating, 29 reviews

Wildbluesea Retreat

TerriRating, 5 stars6 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 favorite
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
5 out of 5 average rating, 3 reviews

114 High Street Luxury Home Downtown Chestertown

KeeganRating, 5 stars2 months ago
Katie's house was perfectly located on the main strip of Chestertown. The house itself was in pristine condition upon our arrival. Was perfect for our group of 7 with plenty of sleeping accommodations, great living spaces to gather, and some historic charm to make us feel right at home. Thanks Katie for a great stay.
Guest favorite
Home in Stevensville
4.91 out of 5 average rating, 78 reviews

Cheerful & Spacious Shore Life Beauty!

CatherineRating, 5 stars2 weeks ago
Stayed here for a wedding at Kent Island resort. Location was great for the wedding - only about 5 minutes away from the venue and 15 minutes away from nightlife. The house had great character and charm. Definitely enjoyed our time here!
Guest favorite
Home in Chestertown
4.93 out of 5 average rating, 43 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

ChristineRating, 5 stars3 weeks ago
Ina was a great communicator - from initial contact, instructions for the house, to checkout! She couldn’t have been better. She was quick to respond and very helpful, which made everything super easy. The house had such an amazing view! Our water-loving dog found the river within 5 mins of getting out of the car!! Great amenities (incl. kayaks, life vests (even for the pup!), well stocked kitchen, bed linens, comfy beds and furniture, nicely decorated, and clean)! It was an easy ride to town. We went to get a bit of a respite from our busy lives for a few days in the off season, and the surroundings were just what we needed. One downside was that the utilities (refrigerator and heat) are rather loud when they turn on, so if you’re a light sleeper, you may be bothered. We were awakened a few times, but the rest of the positives made up for it!! Great spot!
Top guest favorite
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 favorite
Home in Chestertown
4.97 out of 5 average rating, 29 reviews

River Cottage, Chestertown

FranklinRating, 5 stars6 months ago
Beautiful location and the bikes, kayaks and fire pit all added fun and relaxation to our stay! Close enough to Chestertown to enjoy the farmers’ market and shopping and far enough out to be a peaceful retreat.
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
Top guest favorite
Home in Chestertown
5 out of 5 average rating, 37 reviews

Magnolia House: walk to shops, restaurants, river

NancyRating, 5 stars2 months 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.
Top guest favorite
Home in Chester
5 out of 5 average rating, 34 reviews

*Waterfront Sunset Bayview* sleeps 6

MaryRating, 5 stars1 month ago
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!

Private house rentals

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

Bay Beach Oasis

JamesRating, 5 stars6 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 favorite
Home in Grasonville
5 out of 5 average rating, 48 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

MichaelRating, 5 stars4 weeks ago
Great place to stay - we had a quick work trip and it worked out great. Very clean and neat.
Top guest favorite
Home in Rock Hall
5 out of 5 average rating, 29 reviews

1-Particular Harbor: A Coastal Oasis!

EmmaRating, 5 stars5 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!!
Superhost
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 stars6 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 favorite
Home in Annapolis
4.9 out of 5 average rating, 198 reviews

Country House on the Bay

ChristinaRating, 5 stars6 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!
Top guest favorite
Home in Chester
5 out of 5 average rating, 67 reviews

Chester Delight- Fireplace/Deck&Patio+fenced yard

MilissaRating, 5 stars4 months ago
Great place with plenty of room. Very clean and had all amenities that were needed for the stay in the kitchen, bathrooms, and bedrooms. Hosts were very attentive and responsive. Will definitely stay here again when we need a place in the area.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 37 reviews

Bay Home in Annapolis with Private Dock

KennethRating, 5 stars1 week ago
Beautiful, sun-filled house on the bay! We watched the sun rise over the water from the master bedroom. We tried our hand at making lattes on the Rocket Espresso Appartamento machine. The dock was the perfect vantage point to watch birds or ocean-faring boats go out to sea. The kids played ping-pong for hours. The kitchen was a literal chef's kitchen, with a flywheel meat slicer, juice press, air fryer, even a counter-mount wine bottle opener. The owner planned every detail, down to the fire lay in the backyard firepit. We would definitely like to come back again.

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