Vacation Homes in Windsor, CT

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Top Vacation Homes in Windsor

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

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

$267 nightly
The price is $303 total per night
$303 total
Oct 5 - Oct 6
Total with taxes and fees
A water park and a gym are featured at this smoke-free vacation home. Families will appreciate the playground and onsite laundry facilities. A garden and barbecue grills are also provided.
Kitchen
Washer
New!Quaint & Convenient Hideaway: Great Location

New!Quaint & Convenient Hideaway: Great Location

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Stay at this vacation home in East Hartford. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Xfinity Theatre and Cabela's are located nearby.
Kitchen
Air conditioning
Prime West Hartford Center Location: Historic Gem

Prime West Hartford Center Location: Historic Gem

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC

2 out of 5
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Stay at this vacation home in Springfield. Enjoy air conditioning. Popular attractions MGM Springfield and Naismith Memorial Basketball Hall of Fame are located nearby.
Air conditioning
Parking available
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

$250 nightly
The price is $283 total per night
$283 total
Oct 5 - Oct 6
Total with taxes and fees
A gym is featured at this vacation home, along with laundry facilities.
Washer
Dryer
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

$479 nightly
The price is $544 total per night
$544 total
Oct 5 - Oct 6
Total with taxes and fees
This vacation home features laundry facilities.
Kitchen
Washer
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

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

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This vacation home features laundry facilities.
Kitchen
Washer
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

$260 nightly
The price is $295 total per night
$295 total
Oct 7 - Oct 8
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.
Kitchen
Washer
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

$338 nightly
The price is $357 total per night
$357 total
Oct 5 - Oct 6
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Newly Renovated 4 Bedroom House

Newly Renovated 4 Bedroom House

$414 nightly
The price is $435 total per night
$435 total
Oct 12 - Oct 13
Total with taxes and fees
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Linny's Lakeview Cottage - Cozy, fun & updated

Linny's Lakeview Cottage - Cozy, fun & updated

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Family Stays: Middletown, CT

Family Stays: Middletown, CT

$186 nightly
The price is $211 total per night
$211 total
Oct 14 - Oct 15
Total with taxes and fees
This vacation home features a garden, laundry facilities, and barbecue grills.
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.

Top hotels in Windsor

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

200 Corporate Dr, Windsor, CT
$138 nightly
The price is $159 total per night from Oct 30 to Oct 31
$159 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)

Find the Best Vacation Homes in Windsor

Why book a vacation home in Windsor?

Vacation homes in Windsor make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Windsor?

Private Windsor rental homes range between $127 - $544 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Windsor vacation home rentals. You might look for Windsor rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Windsor offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Windsor?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Windsor. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Windsor hotels and vacation homes that best suit your stay. We also have deals for flights, and Windsor car rentals. You’ll save even more when you bundle your items into a Windsor vacation package!

How many vacation homes are available to book in Windsor?

There are 210 rental homes in Windsor. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Windsor?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

Windsor Vacation Homes essential information

Accommodation
210 Vacation Homes
Lowest Price
$127
Highest Price
$544
Popular accommodation
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!, New!Quaint & Convenient Hideaway: Great Location, Prime West Hartford Center Location: Historic Gem, 3-bedroom house in perfect Springfield with WiFi, AC, Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds, Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford, Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield, Lakefront - King - W&D - Fire Pit - Kayaks - SUPs, Big farmhouse in the foothills of the Berkshires, Newly Renovated 4 Bedroom House, Linny's Lakeview Cottage - Cozy, fun & updated, Family Stays: Middletown, CT

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More places to stay in Windsor