Simsbury Cottages

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Cottages in Simsbury

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

Winsted CT

With a stay at this cottage in Winchester, 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.

Westfield Vacation Rental w/ Porch, Pets Welcome!

Westfield MA

When you stay at this cottage in Westfield, you'll be near the beach, within a 5-minute drive of Westfield River and Westfield City Hall.

Cozy Springfield Vacation Rental Near Downtown

Springfield MA

With a stay at this cottage in Springfield (Forest Park), you'll be within a 5-minute drive of MGM Springfield and MassMutual Center.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Plymouth CT

Located in Plymouth, this cottage is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.

Lakefront Home, Close to Mt Southington!

1743 Meriden Rd Wolcott CT

With a stay at this cottage in Wolcott, you'll be within a 5-minute drive of Mattatuck Beach and Mount Southington Ski Area.

Charming Windsor Home w/ Private Backyard!

Windsor CT

Located in Windsor, this cottage is within a 5-minute drive of Connecticut River and Keney Park.

Charming Farmhouse w/ Pool & Fishing Pond!

Bolton CT

Located in Bolton, this cottage is within a 10-minute drive of Bolton Notch State Park and Charter Oak Park.

Modern Terryville Cottage w/ Deck & Lake View!

Terryville CT

Located in Terryville, this cottage is a 4-minute drive from Cedar Lake and 5 minutes from Imagine Nation Children's Museum.

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.

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

Winchester CT

A stay at this cottage places you in the heart of Winsted, steps from Highland Lake and a 2-minute drive from The Marina at Highland Lake.

Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

Litchfield CT

With a stay at this cottage in Litchfield, you'll be within a 10-minute walk of Tapping Reeve House and Law School and Litchfield Town Green.

Lakefront Granby Escape w/ Private Dock & Kayaks!

Granby CT

Located in Granby, this cottage is a 4-minute drive from Town of Granby Open Space and 6 minutes from Grace Kellogg Preserve.

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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.