Windsor Vacation Rentals

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Vacation Rentals in Windsor

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Somers CT

$349 nightly

$395 total

Sep 2 - Sep 3

Total with taxes and fees

With a stay at this vacation home in Somers, you'll be within a 5-minute drive of Sonny's Place and Scantic River State Park.

Kitchen

Washer

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville CT

$464 nightly

$526 total

Aug 10 - Aug 11

Total with taxes and fees

With a stay at this vacation home in Canton (Collinsville), you'll be steps from Farmington River and 5 minutes by foot from Farmington Valley Stage Company.

Kitchen

Washer

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Winchester CT

When you stay at this vacation home in Winsted, you'll be on a lake, just steps from Highland Lake and Burr Pond State Park.

Kitchen

Washer

“3BR Home Near Wesleyan & Downtown Middletown

Middletown CT

$281 nightly

$319 total

Aug 31 - Sep 1

Total with taxes and fees

With a stay at this vacation home in Middletown (Washington Street Historic District), you'll be within a 10-minute walk of Wesleyan University and Kidcity Children's Museum.

Washer

Dryer

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.

Kitchen

Washer

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 Connecticut Convention Center.

Kitchen

Air conditioning

Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Springfield MA

$320 nightly

$363 total

Aug 11 - Aug 12

Total with taxes and fees

With a stay at this vacation home in Springfield (Forest Park), you'll be within a 5-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of Fame.

Kitchen

Washer

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

SPRINGFIELD MA

With a stay at this vacation home in Springfield (Boston Road), you'll be within a 15-minute drive of MGM Springfield and Naismith Memorial Basketball Hall of Fame.

Kitchen

Washer

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

NEW-Another Fun Downtown Location 1st floor

Southington CT

A stay at this vacation home places you in the heart of Southington, within a 15-minute walk of Southington Public Library and Hospital of Central Connecticut.

Kitchen

Washer

Entire guest suite in South Windsor, Connecticut

South Windsor CT

$106 nightly

$119 total

Aug 8 - Aug 9

Total with taxes and fees

With a stay at this vacation home in South Windsor, you'll be within a 15-minute drive of Connecticut Convention Center and South Windsor Bark Park.

Air conditioning

Outdoor Space

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

Bristol CT

Located in Bristol, this vacation home is within a 5-minute drive of Casey Field and Wilson Playground.

Kitchen

Washer

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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.