House vacation rentals in Queen Anne's County

Find and book unique houses on Airbnb

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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 stars8 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.
Superhost
Home in Saint Michaels
4.5 out of 5 average rating, 6 reviews

Family & Friends Paradise – Pool, BBQ, & More!

NicoleRating, 5 stars1 week ago
Gorgeous place with lots of kitchen items stocked. Pool and hut are such an added bonus. Place was so clean and cozy. Being on the water was wonderful as well. Great location to town and Tilghman Island. Would definitely recommend this rental.
Superhost
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars2 weeks ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Guest favorite
Home in Rock Hall
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 month 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 favorite
Home in Rock Hall
5 out of 5 average rating, 15 reviews

The Mariner's House

ErinRating, 5 stars1 month ago
Wonderful property with lots of amenities!
Guest favorite
Home in Chester
4.95 out of 5 average rating, 95 reviews

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars1 week ago
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.
Top guest favorite
Home in Stevensville
5 out of 5 average rating, 29 reviews

Wildbluesea Retreat

TerriRating, 5 stars7 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 stars7 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

Top guest favorite
Home in Rock Hall
5 out of 5 average rating, 14 reviews

Bay Beach Oasis

AaronRating, 5 stars2 weeks ago
We had a great time in Rock Hall, Curtis was an excellent host!
Guest favorite
Home in Annapolis
4.97 out of 5 average rating, 74 reviews

Annapolis USNA Cottage Waterfront Pier Cozy Escape

Nate And KatieRating, 5 stars2 weeks ago
Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities
Guest favorite
Home in Rock Hall
4.96 out of 5 average rating, 55 reviews

Eastern Neck Water Paradise w/Brick oven & Beach

JuanitaRating, 5 stars1 week ago
Our stay at this place was so amazing! It had something for everyone to do! I feel it was very kid-friendly with lots of sand toys, a kiddie pool and inside toy too. The kitchen was well- stocked! We used the brick oven one night and boiled crabs. Martha responded quickly to our questions. She made it very easy for us to get into the house. We most definitely would come back again!
Superhost
Home in Queenstown
4.97 out of 5 average rating, 37 reviews

Unwind on the Wye River

BrianRating, 5 stars1 month ago
Beautiful and well maintained property. This is not an investment property Airbnb, this is someone’s personal vacation home and it shows in the attention to details and how well maintained it is. John also went above and beyond for our stay with a special request. We hope to return for our next golf trip to Queenstown Harbor.
Guest favorite
Home in Stevensville
4.97 out of 5 average rating, 33 reviews

Carolina Cottage - 2 story, pet-free home

GiselleRating, 5 stars2 weeks ago
we were at ease and comfortable staying at Vicki's place for a wedding nearby. all the accomodations were great. kitchen was wonderful and stocked. very clear checkin and checkout instructions. beds were so comfy, especially the mattress in the master suite. my parents liked it so much, they checked the manufacturer and purchased the exact same one for their own bedroom at home!
Superhost
Home in Grasonville
4.75 out of 5 average rating, 4 reviews

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

MeghanRating, 5 stars2 weeks ago
Very responsive host! Amazing home, felt brand new and very clean! Loved the loft area and great restaurants nearby!
Superhost
Home in Denton
4.9 out of 5 average rating, 87 reviews

Historic 19th Century Eastern Shore Farmhouse

PaulRating, 5 stars6 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
Guest favorite
Home in Chestertown
4.94 out of 5 average rating, 72 reviews

Waterfront w/ Hot Tub + Dock | Harbor View Haven

AiyanaRating, 5 stars2 weeks ago
A group of us went to Chestertown, MD for Memorial Day weekend. The house was exactly as described and the host was friendly. There was a full kitchen with everything you’d need and plenty of linen and towels for everyone. I think the space was perfect and had so much to offer for a great price.

Private house rentals

Guest favorite
Home in Chestertown
4.97 out of 5 average rating, 88 reviews

River front cottage with private dock & water fun

RichardRating, 5 stars3 months ago
Great location. Caroline was amazing. Look forward to renting again next year!!
Guest favorite
Home in Rock Hall
4.9 out of 5 average rating, 30 reviews

Spacious Victorian close to everything in RH!

LisaRating, 5 stars2 weeks ago
Lovely immaculately clean home close to rock hall marinas. The beds were really comfortable and hosts super responsive. Loved all the books and board games they had. Kitchen very well stocked. Highly recommend staying here.
Top guest favorite
Home in Chestertown
5 out of 5 average rating, 41 reviews

Magnolia House: walk to shops, restaurants, river

AliceRating, 5 stars2 weeks ago
Wow! This place is perfectly located to enjoy both the historic downtown and the river. The provided parking spot was super convenient, and we walked almost everywhere during our stay. It is less than 3 minutes walk to the main street and less than 5 minutes walk to the town dock where we enjoyed a lovely boat ride and brunch one day. The grounds provide lots of private seating areas and a screened in porch to enjoy nature (we saw lots of squirrels and a family of blue jays while there), and the inside of the home is decorated in a period style. The beds were comfy, and the kitchen was well stocked. The host was also very responsive providing helpful instructions and guidance to help us make the most out of our stay. From an electric charger for the car to logs for the fire pit to lots of fun games in the library, the host has added lots of thoughtful touches. Thank you for a great stay!
Guest favorite
Home in Chester
5 out of 5 average rating, 13 reviews

Spacious waterfront home private pier dog-friendly

DanRating, 5 stars1 month ago
The property, location, house set-up, and communications from the management during our 6 day stay was amazing. Literally the best low-key, relaxing experience I have ever had in recent memory. The house has everything you need for a great peaceful stay, especially if you are just hanging with a small group of close friends. Cooking is particularly awesome, as this property has a great wide open kitchen. The grounds are beautiful. We spent most of our time on the main floor in the kitchen and then on the long beautiful dock where we did some fishing and first time crabbing just for fun. The town nearby and neighborhood is so nice. Not far from Annapolis, MD at all if you want to visit. But honestly, the property alone is so nice to just to stay in and just relax. Great space with some homey accommodations. Big shout outs to one of the property management team members, Melissa. She was so very helpful. Will be back again next year!
Top guest favorite
Home in Stevensville
5 out of 5 average rating, 46 reviews

Away at the Bay: New Home on the Chesapeake Bay!

PaigeRating, 5 stars1 week ago
Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.
Top guest favorite
Home in Chestertown
5 out of 5 average rating, 39 reviews

In Town Chestertown Rancher (1 Block to College)

MichelleRating, 5 stars1 week ago
Tim was very attentive to ensure we had a smooth check-in and if we needed anything throughout our stay. The place was comfortable and inviting. We also appreciated the small touches for our arrival. I definitely recommend this place to stay.
Top guest favorite
Home in Chester
5 out of 5 average rating, 73 reviews

Chester Delight- Fireplace/Deck&Patio+fenced yard

ChelseaRating, 5 stars2 weeks ago
The house was clean and perfect place to stay while we visited friends in the area. Reg and Julia were very nice and communicative!
Top guest favorite
Home in Stevensville
5 out of 5 average rating, 36 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

ShadRating, 5 stars2 weeks ago
We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

Destinations to explore