Tolland Cottages

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Cottages in Tolland

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough MA

Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA

Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.

Waterfront Cottage 10 Min From Great Barrington

New Marlborough MA

With a stay at this cottage in Great Barrington, you'll be steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Winsted CT

With a stay at this cottage in Winsted, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls MA

Located in Ashley Falls, this cottage is within a 5-minute drive of Ashley Falls Woods and Bartholomew's Cobble.

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA

With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.

Westfield Vacation Rental w/ Porch, Pets Welcome!

Westfield MA

With a stay at this cottage in Westfield, you'll be near the beach, just a 4-minute walk from Stanley Park and 8 minutes by foot from Westfield River.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

325 Long Pond Road Great Barrington MA

Located in Great Barrington, this cottage is within a 10-minute drive of Art et Industrie and Housatonic River.

Historic Huntington Home - Walk to Westfield River

Huntington MA

With a stay at this cottage in Huntington, you'll be within a 5-minute drive of Huntington Public Library and Hillgate Park.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

21 Saint James Avenue Lee MA

With a stay at this cottage in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Lakefront Tranquility/Fishermans Delight

New Hartford CT

Located in New Hartford, this cottage is on the waterfront, a 1-minute drive from Brodie Park and 7 minutes from New Hartford Free Public Library.

Stockbridge Home: Walk to Town Beach!

Stockbridge MA

With a stay at this cottage in Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.