
House vacation rentals in Queen Anne's County
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Top-rated house rentals in Queen Anne's County
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Popular amenities for Queen Anne's County house rentals
House rentals with a pool

Chestertown Watson Family Farm
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.

Rockfish Keeper
The house was exactly as described and it was so easy to communicate with them as they responded to texts within minutes

The Mariner's House
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!

Waterfront Farmhouse Meets Modern Luxury
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.

10 Minutes to St. Michaels with a Private Pool
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.🥰

Wildbluesea Retreat
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!

Bayside Escape
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

114 High Street Luxury Home Downtown Chestertown
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.

Cheerful & Spacious Shore Life Beauty!
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!

Waterfront Paradise w/ Pier - kayak to Chestertown
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!

Sleeps12*MainHouse+DetachedApt*Wedding Venues&USNA
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.

River Cottage, Chestertown
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.

Unwind on the Wye River
beautiful spacious home. great for my family of 6 to meet up with our USNA midshipmen. loved the back yard and living rooms

Magnolia House: walk to shops, restaurants, river
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.

*Waterfront Sunset Bayview* sleeps 6
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!
Private house rentals

Bay Beach Oasis
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.

Bay Breeze - 3BR Waterfront Chester River Retreat
Great place to stay - we had a quick work trip and it worked out great. Very clean and neat.

1-Particular Harbor: A Coastal Oasis!
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!!

Historic 19th Century Eastern Shore Farmhouse
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

Crab Alley Bay House, Waterfront Home w Hot Tub
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!

Country House on the Bay
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!

Chester Delight- Fireplace/Deck&Patio+fenced yard
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.

Bay Home in Annapolis with Private Dock
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.
Destinations to explore
- Rentals with a fire pit Queen Anne's County
- Rentals with pools Queen Anne's County
- Rentals with lake access Queen Anne's County
- Waterfront rentals Queen Anne's County
- Rentals with a washer and dryer Queen Anne's County
- Kid-friendly rentals Queen Anne's County
- Rentals with beach access Queen Anne's County
- Rentals with outdoor seating Queen Anne's County
- Rentals with a kayak Queen Anne's County
- Rentals with a fireplace Queen Anne's County
- Beachfront rentals Queen Anne's County
- Rentals with breakfast Queen Anne's County
- Rentals with a hot tub Queen Anne's County
- Rentals with a patio Queen Anne's County
- Pet-friendly rentals Queen Anne's County
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- Nationals Park
- The White House
- Lincoln Park
- National Mall
- Hampden
- National Museum of African American History and Culture
- Sandy Point State Park
- Smithsonian American Art Museum
- Smithsonian National Museum of Natural History
- Big Stone Beach
- Patterson Park
- National Air and Space Museum
- Washington Monument
- Oriole Park at Camden Yards
- District Wharf
- Heritage Shores
- Six Flags America
- American African Museum
- Meridian Hill Park
- Killens Pond State Park
- M&T Bank Stadium
- Gerry Boyle Park
- Quiet Waters Park
- Maryland Renaissance Festival
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