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.

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-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

R7,114 ZAR per night
Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook 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

R4,346 ZAR per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern 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

R1,921 ZAR per night

Popular amenities for Tolland vacation rentals

Other great vacation rentals in Tolland

Superhost

Cabin in Otis

4.86 out of 5 average rating, 400 reviews

Cozy cabin in the Berkshires

Jun 6 – 13

R3,359 ZAR per night
Guest favorite

Apartment in Sheffield

5.0 out of 5 average rating, 318 reviews

Hideaway with Spectacular Berkshire Views

Nov 22 – 29

R3,139 ZAR per night
Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 102 reviews

Private 2nd-floor studio on a working produce farm

Apr 10 – 17

R1,962 ZAR per night
Guest favorite

Apartment in Great Barrington

4.95 out of 5 average rating, 314 reviews

Private En Suite in Beautiful Victorian

Mar 18 – 25

R2,096 ZAR per night
Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 reviews

Gingerbread House Tower in the Berkshire Hills

May 9 – 16

R5,179 ZAR per night
Guest favorite

Home in Southwick

4.99 out of 5 average rating, 177 reviews

Linny's Lakeview Cottage

Jul 31 – Aug 7

R3,281 ZAR per night
Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 257 reviews

Relaxing secluded stay with loving social animals.

Jan 13 – 20

R2,970 ZAR per night
Guest favorite

Cottage in Great Barrington

4.91 out of 5 average rating, 223 reviews

Cottage on Scenic Road

Nov 5 – 12

R2,578 ZAR per night
Superhost

Home in Tolland

4.9 out of 5 average rating, 20 reviews

Beautiful Home In Private Wooded Community

Mar 1 – 8

R5,413 ZAR per night
Guest favorite

Home in Otis

4.82 out of 5 average rating, 56 reviews

Wintertime Oasis in the Berkshires

Jun 23 – 30

R2,321 ZAR per night
Superhost

Home in Sandisfield

4.95 out of 5 average rating, 20 reviews

Design Cottage on a Trout River. Fly Fishing Spot!

May 14 – 21

R3,098 ZAR per night
Superhost

Apartment in Winsted

4.85 out of 5 average rating, 60 reviews

Haven at Highland lake

Feb 5 – 12

R1,110 ZAR per night

Destinations to explore

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