House holiday 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 favourite
Home in Chestertown
5 out of 5 average rating, 23 reviews

Chestertown Watson Family Farm

LukeRating, 5 stars1 week ago
We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!
Superhost
Home in Queenstown
5 out of 5 average rating, 3 reviews

Pintail Point Cottage

MatthewRating, 5 stars2 weeks ago
Beautiful location. Cottage was nice and cozy.
Guest favourite
Home in Rock Hall
4.95 out of 5 average rating, 38 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 favourite
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 favourite
Home in Chester
4.95 out of 5 average rating, 95 reviews

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars3 weeks 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.
Superhost
Home in Saint Michaels
4.58 out of 5 average rating, 12 reviews

10 Minutes to St. Michaels with a Private Pool

SarahRating, 5 stars1 week ago
This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!
Top Guest favourite
Home in Stevensville
5 out of 5 average rating, 16 reviews

Bayside Escape

JohnRating, 5 stars4 days ago
Our family of 3 had an amazing vacation on our 4 day stay. It was so peaceful and relaxing. The place was exceptionally clean and organized with everything needed. Amazing views on the water and pool was great. We had some rainy weather but still managed enough dry time to enjoy the pool and outdoors
Superhost
Home in Millington
4.86 out of 5 average rating, 65 reviews

The Peaceful Getaway (with private pool & hot tub)

KorynRating, 5 stars6 days ago
Perfect for a family getaway and retreat. Love how child friendly their home was as well!

Weekly house rentals

Guest favourite
Home in Annapolis
4.97 out of 5 average rating, 74 reviews

Annapolis USNA Cottage Waterfront Pier Cozy Escape

Nate And KatieRating, 5 stars4 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 favourite
Home in Chester
5 out of 5 average rating, 15 reviews

Spacious waterfront home private pier dog-friendly

KarenRating, 5 stars1 week ago
The accommodations did not disappoint! Fabulous view, fun choices to take advantage of on the water, great neighborhood and local seafood restaurants! Our family gathering was memorable as a result of this venue! Will be sure to return!
Top Guest favourite
Home in Chestertown
5 out of 5 average rating, 78 reviews

Lovely Home in Chestertown With Free EV Charging

SheridanRating, 5 stars1 week ago
Perfect place for our during a nearby wedding. Teddi was always responsive, pleasant, and helpful.
Top Guest favourite
Home in Stevensville
5 out of 5 average rating, 46 reviews

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

PaigeRating, 5 stars3 weeks 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 favourite
Home in Chestertown
4.94 out of 5 average rating, 94 reviews

Simple Living on the Pond

CarverRating, 5 stars3 months ago
Lovely house in a beautiful and peaceful setting. Well equipped kitchen, bathroom and cozy, comfortable bedding and beds! I recommend Diana’s place for a peaceful and relaxing stay.
Top Guest favourite
Home in Stevensville
5 out of 5 average rating, 31 reviews

Screened Porch | Near Bay Bridge & USNA | Big Yard

JenRating, 5 stars2 weeks ago
Karin was very responsive to our last minute booking. The house was as described and directions were clear. We cannot thank the hosts for assisting us during a difficult time.
Top Guest favourite
Home in Rock Hall
5 out of 5 average rating, 99 reviews

Cozy 1920's Bungalow Near Water/Local Attractions

MatthewRating, 5 stars3 weeks ago
We had a wonderful stay and the host was very accommodating! Her flexibility was good and location is great for getting around rockhall! I would recommend this place
Top Guest favourite
Home in Rock Hall
5 out of 5 average rating, 90 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

AnnaRating, 5 stars2 weeks ago
We loved our stay in Rock Hall! It was our 3rd trip to the area and Jim's place was our favorite. We loved walking and biking everywhere including the restaurants and the beach! The front porch and back patio were great outside spots to relax. We enjoyed grilling dinner one night and using the yard games in the shed. We hope to be back soon!

Private house rentals

Guest favourite
Home in Stevensville
4.97 out of 5 average rating, 71 reviews

Cozy home with Screened Porch, Min from Weddings

GregRating, 5 stars1 month ago
Great little place. Convenient to the island and the venues
Top Guest favourite
Home in Rock Hall
5 out of 5 average rating, 15 reviews

Bay Beach Oasis

CarolineRating, 5 stars3 weeks ago
Not only was our stay reasonably priced it was spacious and well equipped. Check out the Bed & Breakfast that is directly behind the house for a good bite to eat! A nice perk was the small community beach was in walking distance.
Guest favourite
Home in Chestertown
4.94 out of 5 average rating, 69 reviews

Beautifully remodeled home in Historic Chestertown

SharonRating, 5 stars3 weeks ago
This was a lovely place to stay on the eastern shore of Maryland. The house was clean and a perfect place to stay the night before our triathlon.
Guest favourite
Home in Chestertown
4.97 out of 5 average rating, 89 reviews

River front cottage with private dock & water fun

MatthewRating, 5 stars2 weeks ago
The home was lovely, right on the river, and felt....homey. It was the kind of place I would have if I had a home on the river. There were friendly neighbors who gave us some advice on what to do/not to do in the area and we had a lovely time. This might just be an annual trip for me and my extended family.
Top Guest favourite
Home in Stevensville
5 out of 5 average rating, 21 reviews

Chessie Cottage - Chesapeake Bay

CarolineRating, 5 stars1 month ago
We had the BEST time staying at this beautiful home this past weekend while we were in town for a wedding. The location is absolutely perfect for a peaceful weekend on the water and this house is a DREAM. Thank you so much for letting us stay at your incredible home!
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.
Superhost
Home in Denton
4.9 out of 5 average rating, 88 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 favourite
Home in Sparrows Point
4.93 out of 5 average rating, 43 reviews

Chesapeake Bay, Waterfront Home near Baltimore

AlanaRating, 5 stars2 weeks ago
I had a wonderful weekend stay at Erika's house! The house was nice and comfortable and the location was perfect. We walked to both of the restaurants, which were great, and both had playground areas for kids. We used Erika's kayaks to paddle to Pleasure Island which was the highlight of our trip! I would recommend staying here for a fun stay on the water.

Destinations to explore