House holiday rentals in Queen Anne's County

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Queen Anne's County

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 stars7 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
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 week ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Top guest favourite
Home in Rock Hall
5 out of 5 average rating, 13 reviews

The Mariner's House

VivianRating, 5 stars1 month 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, 91 reviews

Waterfront Farmhouse Meets Modern Luxury

JayRating, 5 stars1 month 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 stars8 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 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 favourite
Home in Stevensville
5 out of 5 average rating, 15 reviews

Bayside Escape

StacyRating, 5 stars6 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 stars7 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, 78 reviews

Cheerful & Spacious Shore Life Beauty!

CatherineRating, 5 stars4 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 favourite
Home in Chestertown
4.93 out of 5 average rating, 43 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

ChristineRating, 5 stars1 month 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 favourite
Home in Stevensville
5 out of 5 average rating, 7 reviews

Sleeps12*MainHouse+DetachedApt*Wedding Venues&USNA

MayaRating, 5 stars5 months ago
My family came down for our cousins wedding and had a wonderful time. The house and guest house were perfect everything was clean and inviting upon our arrival.
Top guest favourite
Home in Chestertown
4.97 out of 5 average rating, 29 reviews

River Cottage, Chestertown

FranklinRating, 5 stars7 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 stars5 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 favourite
Home in Chestertown
5 out of 5 average rating, 38 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 favourite
Home in Chester
5 out of 5 average rating, 34 reviews

*Waterfront Sunset Bayview* sleeps 6

MaryRating, 5 stars2 months ago
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!

Private house rentals

Guest favourite
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 favourite
Home in Grasonville
5 out of 5 average rating, 51 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

RachelRating, 5 stars2 days ago
This riverside house had stunning views from sunrise to sunset and was a perfect place to stay for a golf vacation for our family. The kitchen had everything we needed and the rooms were spacious with comfy mattresses. Everything was wonderful and as advertised.
Top guest favourite
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 stars5 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
4.78 out of 5 average rating, 9 reviews

Crab Alley Bay House, Waterfront Home w Hot Tub

JasmyneRating, 5 stars4 months ago
The place was beautiful clean and came with everything !
Guest favourite
Home in Annapolis
4.9 out of 5 average rating, 199 reviews

Country House on the Bay

AnitaRating, 5 stars5 months ago
Steve is a wonderful host. He greeted us warmly and gave us a very thorough tour of the house. He had recommendations for everything local that was of interest to us. He has a beautiful home and a beautiful setting on the water.
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 39 reviews

Bay Home in Annapolis with Private Dock

DavidRating, 5 stars4 days ago
The description of Joel's Annapolis home is an accurate description of his wonderful home. The most outstanding features of this property are: the waterfront location --> unobstructed panoramic views; serene setting on a quiet street and there are lots of other pluses. The house was super comfortable. Everything was in working order. I appreciated the workout equipment --> not lots of stuff but enough to get some indoor exercise that I like to do each day. Walking up and down the street --> neighbors were all very friendly. The kitchen is fabulous. It only took about 15 to 20 minutes to get to the center of things to do and see in Annapolis. While we did not use much of the outside furniture, the outside furniture is plentiful and looks comfortable. A big thing for us is cleanliness --> the house is immaculate. We will probably make a return trip in the future and would appreciate the opportunity to stay here again.
Guest favourite
Home in Annapolis
4.95 out of 5 average rating, 73 reviews

Serene Riverfront Home

ChristinaRating, 5 stars3 weeks ago
From start to finish, Scott was extremely proactive and responsive to ensure that my group had a good stay. The house is beautifully designed and was very spacious. With the open space layout, my group was able to feel like we weren't too separated, yet at the same time, didn't feel like we were too crowded. The bedrooms and bathrooms worked really well for our group of 5, and we all agreed that this Airbnb was beautiful. We were close to the main area of Annapolis and got to explore the area easily. The weather wasn't great, so we weren't able to explore the area or spend time in the backyard, but it looked beautiful back there. My only suggestion would've been to add some blinds to the house, as it's very exposed at night, but other than that, I'd be happy to stay here again! Scott was a great host.

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