Vacation rentals with outdoor seating in Chestertown
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Chestertown
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chestertown outdoor seating rentals
House rentals with outdoor seating
Home in Riviera Beach
4.94 out of 5 average rating, 124 reviewsWaterfront Cheerful 5 home
Home in Stevensville
4.93 out of 5 average rating, 182 reviewsRelax on Kent Island in 3 Bedroom Home w/Waterview
Home in Edgewater
4.96 out of 5 average rating, 143 reviewsAnnapolis Area Waterside Retreat
Home in Edgewater
4.95 out of 5 average rating, 98 reviewsSpacious 3 Bedrooms House+Patio
Home in Annapolis
5 out of 5 average rating, 120 reviewsHistoric & sunny home steps from USNA/downtown
Home in Greensboro
4.97 out of 5 average rating, 149 reviewsCozy Riverside Cottage in the Woods
Home in Chestertown
5 out of 5 average rating, 64 reviewsLovely Home in Chestertown With Free EV Charging
Home in Rock Hall
4.84 out of 5 average rating, 127 reviewsPirates Perch
Apartment rentals with outdoor seating
Rental unit in Annapolis
4.98 out of 5 average rating, 133 reviewsOld Orchard Cottage
Rental unit in Sparrows Point
4.98 out of 5 average rating, 46 reviewsSafe, quiet neighborhood close to downtown!
Rental unit in Chestertown
4.89 out of 5 average rating, 74 reviews1-br apt in downtown Chestertown (Unit 1)
Rental unit in Arnold
4.96 out of 5 average rating, 174 reviewsFall Getaway
Rental unit in Chestertown
5 out of 5 average rating, 11 reviewsCozy One Bed/One Bath Apartment in Chestertown
Rental unit in Annapolis
4.93 out of 5 average rating, 129 reviewsWalk to Water, State House, USNA
Rental unit in Worton
4.97 out of 5 average rating, 30 reviewsElliott House Historic Home Near Chesapeake Bay
Rental unit in Betterton
5 out of 5 average rating, 15 reviewsBayside Bungalow
Condo rentals with outdoor seating
Condo in Annapolis
4.99 out of 5 average rating, 134 reviewsNew Downtown Annapolis Condo With Free Parking
Condo in Chestertown
New place to stayHistoric Downtown Loft | Park View | Onsite Spa
Condo in Annapolis
4.8 out of 5 average rating, 60 reviewsAnchors Away
Private room in Annapolis
5 out of 5 average rating, 11 reviewsCharming Condo, with Private Bedroom & Bathroom
Condo in Annapolis
4.76 out of 5 average rating, 80 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
Condo in Annapolis
5 out of 5 average rating, 51 reviewsCharming Annapolis Waterfront Condo
Condo in Betterton
4.92 out of 5 average rating, 36 reviews3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
Condo in Annapolis
4.5 out of 5 average rating, 4 reviewsWalk to Main St Waterfront condo, pool, parking
Quick stats about vacation rentals with outdoor seating in Chestertown
Total rentals
20 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Rentals with outdoor seating United States
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- Rentals with outdoor seating Maryland
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