Windsor Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Windsor hotels

Cottages in Windsor

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.

Kitchen

Free WiFi

Charming Cottage by the Lake❤️

Coventry CT

With a stay at this cottage in Coventry (Coventry Lake), you'll be within a 15-minute drive of University of Connecticut and Nathan Hale Homestead.

Kitchen

Washer

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.

Kitchen

Washer

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

East Hampton CT

With a stay at this cottage in East Hampton (Lake Pocotopaug), you'll be within a 10-minute drive of Lake Terramuggus and Comstock Bridge.

Kitchen

Washer

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.

Kitchen

Washer

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.

Kitchen

Washer

Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.

East Hampton CT

With a stay at this cottage in East Hampton (Lake Pocotopaug), you'll be a 2-minute drive from Day Pond State Park and 5 minutes from Lake Terramuggus.

Kitchen

Washer

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.

Pool

Kitchen

Lake Getaway at Coventry Lake! close to Uconn

Coventry CT

With a stay at this cottage in Coventry (Coventry Lake), you'll be within a 10-minute drive of University of Connecticut and J. M. Sarnik & Sons' The Old General Store.

Kitchen

Washer

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.

Kitchen

Free WiFi

Lakefront Connecticut Retreat Near Uconn

Coventry CT

With a stay at this cottage in Coventry, you'll be within a 5-minute drive of University of Connecticut and J. M. Sarnik & Sons' The Old General Store.

Kitchen

Pet friendly

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.

Kitchen

Free WiFi

Don't see what you're looking for?

See all available properties in Windsor

View all properties

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.