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 Annapolis
4.99 out of 5 average rating, 199 reviewsCape St Claire waterfront getaway
Aug 1 – 8
Home in Grasonville
4.94 out of 5 average rating, 226 reviewsRiver Front, Private Single Family Home
Nov 17 – 24
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Nov 30 – Dec 7
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Dec 25 – Jan 1
Home in Chestertown
4.98 out of 5 average rating, 44 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
Jun 5 – 12
Home in Chestertown
4.96 out of 5 average rating, 73 reviewsCozy 3-bedroom home w/ screened in porch & firepit
Oct 3 – 10
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsNEW Chestertown Retreat
Sep 29 – Oct 6
Apartment rentals with outdoor seating
Apartment in Crownsville
4.98 out of 5 average rating, 165 reviews“River Sweet" Private Apartment
Oct 21 – 28
Apartment in Stevensville
4.98 out of 5 average rating, 240 reviewsBoutique by the Bay
Dec 30 – Jan 6
Apartment in Chester
4.97 out of 5 average rating, 234 reviewsCozy Waterfront Apartment Chester, MD
Apr 8 – 15
Apartment in Baltimore
4.78 out of 5 average rating, 369 reviewsAwesome studio tucked away & Centrally located !
Jul 5 – 12
Apartment in Annapolis
4.92 out of 5 average rating, 110 reviewsWalk to Water, State House, USNA
Jul 8 – 15
Apartment in Annapolis
4.91 out of 5 average rating, 122 reviewsChesapeake Bird Nest
Aug 18 – 25
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Jan 16 – 23
Apartment in Annapolis
4.98 out of 5 average rating, 124 reviewsOld Orchard Cottage
Jan 1 – 8
Condo rentals with outdoor seating
Condo in Annapolis
4.99 out of 5 average rating, 126 reviewsNew Downtown Annapolis Condo With Free Parking
Jul 29 – Aug 5
Condo in Annapolis
4.73 out of 5 average rating, 71 reviewsAmazing Views from Spa Creek 2BD Condo with Pool
Nov 17 – 24
Condo in Annapolis
4.89 out of 5 average rating, 27 reviewsModern Upcale Condo wparking in downtown Annapolis
Dec 13 – 20
Condo in Annapolis
4.89 out of 5 average rating, 45 reviewsAnchors Away
Mar 20 – 27
Condo in Annapolis
4.97 out of 5 average rating, 70 reviewsSpring into Annapolis-very low cleaning fee
Jan 21 – 28
Condo in Annapolis
4.96 out of 5 average rating, 54 reviewsFunky Uptown Apt meets Downtown - Hist District
Aug 17 – 24
Condo in Rock Hall
5.0 out of 5 average rating, 10 reviewsWaterman's Delight ~ Best Harbor View Sunsets!
Jan 27 – Feb 3
Condo in Betterton
4.93 out of 5 average rating, 30 reviews3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
Jun 25 – Jul 2
Quick stats about vacation rentals with outdoor seating in Chestertown
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
G$18,811 GYD before taxes and fees
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