Windsor Vacation Rentals

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Vacation Rentals in Windsor

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Windsor CT

With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of The Meadows Music Theatre and Loomis Chaffee School.

Kitchen

Air conditioning

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Coventry CT

With a stay at this vacation home in Coventry, you'll be on the waterfront, within a 5-minute drive of University of Connecticut and Coventry Lake.

Kitchen

Washer

Cozy & Spacious Entire Home in Springfield

Springfield MA

$303 nightly

$344 total

Sep 28 - Sep 29

Total with taxes and fees

With a stay at this vacation home in Springfield (Forest Park), you'll be within a 15-minute drive of MGM Springfield and Six Flags New England.

Kitchen

Washer

Island Vibes Home

Windsor CT

With a stay at this vacation home in Windsor, you'll be within a 10-minute drive of The Meadows Music Theatre and Loomis Chaffee School.

Kitchen

Washer

Family Stays: Middletown, CT

Middletown CT

$205 nightly

$233 total

Oct 12 - Oct 13

Total with taxes and fees

With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of General Mansfield House and Wesleyan University.

New!Quaint & Convenient Hideaway: Great Location

East Hartford CT

With a stay at this vacation home in East Hartford, you'll be within a 10-minute drive of The Meadows Music Theatre and East Hartford Shopping Center.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks CT

$487 nightly

$551 total

Sep 23 - Sep 24

Total with taxes and fees

With a stay at this vacation home in Windsor Locks, you'll be within a 15-minute drive of Six Flags New England and Broad Brook Brewing.

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT

With a stay at this vacation home 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.

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

SPRINGFIELD MA

$326 nightly

$370 total

Sep 23 - Sep 24

Total with taxes and fees

With a stay at this vacation home in Springfield (Boston Road), you'll be within a 15-minute drive of MGM Springfield and Lake Lorraine State Park.

Beautifully Renovated First-Floor Apartment Getaway

Springfield MA

$337 nightly

$382 total

Sep 30 - Oct 1

Total with taxes and fees

With a stay at this vacation home in Springfield (Forest Park), you'll be within a 15-minute drive of MGM Springfield and Six Flags New England.

Kitchen

Washer

NEW-Another Fun Downtown Location 1st floor

Southington CT

A stay at this vacation home places you in the heart of Southington, within a 10-minute walk of Barnes Museum and Southington Public Library.

Historical Blvd. Cheney Bros HillTop Mansion

Manchester CT

A stay at this vacation home places you in the heart of Manchester, within a 5-minute drive of Manchester Memorial Hospital and Lutz Children's Museum.

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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.