Vacation rentals in Tolland
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Top-rated vacation rentals in Tolland
Guests agree: these stays are highly rated for location, cleanliness, and more.
Chalet in Otis
4.94 out of 5 average rating, 346 reviewsMid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
Jun 13 – 20
Home in Colebrook
4.99 out of 5 average rating, 200 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.
Feb 25 – Mar 4
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
Sep 13 – 20
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Tolland vacation rentals
Other great vacation rentals in Tolland
Cabin in Otis
4.86 out of 5 average rating, 400 reviewsCozy cabin in the Berkshires
Jun 6 – 13
Apartment in Sheffield
5.0 out of 5 average rating, 318 reviewsHideaway with Spectacular Berkshire Views
Nov 22 – 29
Farm stay in Pittsfield
4.99 out of 5 average rating, 102 reviewsPrivate 2nd-floor studio on a working produce farm
Apr 10 – 17
Apartment in Great Barrington
4.95 out of 5 average rating, 314 reviewsPrivate En Suite in Beautiful Victorian
Mar 18 – 25
Treehouse in Tyringham
5.0 out of 5 average rating, 222 reviewsGingerbread House Tower in the Berkshire Hills
May 9 – 16
Home in Southwick
4.99 out of 5 average rating, 177 reviewsLinny's Lakeview Cottage
Jul 31 – Aug 7
Farm stay in Ancram
4.95 out of 5 average rating, 257 reviewsRelaxing secluded stay with loving social animals.
Jan 13 – 20
Cottage in Great Barrington
4.91 out of 5 average rating, 223 reviewsCottage on Scenic Road
Nov 5 – 12
Home in Tolland
4.9 out of 5 average rating, 20 reviewsBeautiful Home In Private Wooded Community
Mar 1 – 8
Home in Otis
4.82 out of 5 average rating, 56 reviewsWintertime Oasis in the Berkshires
Jun 23 – 30
Home in Sandisfield
4.95 out of 5 average rating, 20 reviewsDesign Cottage on a Trout River. Fly Fishing Spot!
May 14 – 21
Apartment in Winsted
4.85 out of 5 average rating, 60 reviewsHaven at Highland lake
Feb 5 – 12
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