
Vacation rentals with outdoor seating in Kent County
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Top-rated outdoor seating rentals in Kent County
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House rentals with outdoor seating

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.

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.

2 Beds, 2.5 Baths, Perfect Downtown Location
Easy check-in, great location, bedroom each had a bathroom and a half bath downstairs. Very pleasant stay- we would definitely come back again.

In Town Chestertown Rancher (1 Block to College)
This was a perfect home for a 60th celebration. The home was spotless, beds so comfortable, kitchen well appointed. Host left touches for guests to feel comfortable and welcomed. Quiet neighborhood, great backyard and close enough to walk to stores, resturants and Washington College. I would highly recommend this home for a familiy or friends get away.

Peaceful Acres Guest House (A Nature's Getaway)
The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.

Lotus House: porches, decks, yard, beach access
We had a great stay here, very relaxing. The home is very comfortable. We were there in January, so we appreciated the space and comfort.

Water Views in Rock Hall
Both hosts were so responsive to my questions. The house had everything I needed truly for my guests and I to enjoy ourselves. The surround sound system was such a nice touch. All the bathrooms were nice and the kitchen had everything in terms of utensils to cook fab meals. It is in the very rural side of Maryland and there isn’t a ton to do, but wow the house was beautiful and beyond peaceful.

The Peaceful Getaway (with private pool & hot tub)
it's beautiful and peaceful ❣️ place to visit. all my family love it and Martha is a great host. I appreciate it 🙏 hopefully I'll visit it again
Apartment rentals with outdoor seating

Traveler Guest Suite - Cinnamon By The Bay
Deborah was a great host! Very communicative and helpful when we had questions. The contactless checkin could not have been easier. The place was super clean and had the things you need to be comfortable. We loved that it was right in town and very walkable to restaurants, grocery store, West Marine and the hardware store. It’s the perfect spot for boat cruisers who have a boat on the hard and can’t live aboard while doing the work.

114 High Street First Floor Unit Chestertown
I have stayed at this property before and it is always a great experience. Katie is a wonderful, responsive, host. The welcome basket and handwritten note are thoughtful details. I very much look forward to my next opportunity to stay in Katie’s house again.

Elliott House Historic Home Near Chesapeake Bay
Good communication, worked with us on check in and checkout really great host

Inspiration Guest Suite - Cinnamon By The Bay
Comfortable, self-contained, with full kitchenette. Hotel-level of cleanliness. Comfortable bed. Short walk to bayside. Short drive to the stunning Eastern Neck Wildlife Refuge, a must see. In winter many of the surrounding shops have limited hours or are closed.

1-br apt in downtown Chestertown (Unit 1)
We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!
Condo rentals with outdoor seating

Historic Loft w/ Park View & Spa Access
We enjoyed our long weekend stay in Chestertown. The Park Row AirBnB was exactly like the photos. It was clean, comfortable and was perfectly located in town and there was ample parking directly in front of the AirBnb building. We walked to everything the town had to offer. If you plan to book a stay, the town has a lot to offer in terms of art galleries and outdoor sculptures. And there is a wonderful craft/farmers market every Saturday morning that runs along the main street of town. It was fabulous! We had a very enjoyable stay!

Beach Haven Hideout
This apartment was perfect for our family get together. Although we had a short stay, every detail made us feel very welcome. Michelle was very helpful and promptly mer our needs.

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.

Best kept secret beach-condo on the Chesapeake Bay
Great host who was responsive. Wonderful space with well appointed kitchen. Will be back.
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- Betterton Beach
- Hampden
- Longwood Gardens
- Sandy Point State Park
- Six Flags America
- Big Stone Beach
- Oriole Park at Camden Yards
- Patterson Park
- Heritage Shores
- Killens Pond State Park
- DuPont Country Club
- M&T Bank Stadium
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- Gerry Boyle Park
- Idlewilde Restoration Project
- Quiet Waters Park
- Bulle Rock Golf Course
- Quiet Waters Dog Beach
- Severn Beach
- Sparrows Beach
- Matapeake Clubhouse and Beach
- Flounder Pavilion Beach Front - Sandy Point State Park
- Downs Park Dog Beach