Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Windsor

Fridge, microwave, oven, stovetop
A “Wow” Experience everywhere there is something to stimulate your mind Interest

A “Wow” Experience everywhere there is something to stimulate your mind Interest

Windsor
9.2 out of 10, Wonderful, (10)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
United States
Michael L.
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Downtown Hartford
8.4 out of 10, Very Good, (23)
"Very clean and spacious! Loved all the amenities. Room itself was a bit echoey, but nice and quiet."
United States
Kiara
$135 nightly
The price is $152
Dec 1 - Dec 2
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

Downtown Hartford
9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveler
$218 nightly
The price is $247
Nov 18 - Nov 19
Total with taxes and fees
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC

Downtown Hartford
8.6 out of 10, Excellent, (11)
"Great!"
United States
Sahai S.
$135 nightly
The price is $152
Nov 26 - Nov 27
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Full-size fridge, microwave, oven, dishwasher
Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway

3.5 star property
Forest Park
$589 nightly
The price is $649
Dec 15 - Dec 16
Total with taxes and fees
Newly Renovated 2 floor Getaway
Smart TV, fireplace, video games, books
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!

Forest Park
9.8 out of 10, Exceptional, (36)
"We were traveling to a horse show for 2 nights and this was a close and safe home. Comfortable beds and amazing water pressure in the shower! Very clean as well."
United States
Amy M.
$293 nightly
The price is $332
Dec 1 - Dec 2
Total with taxes and fees
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$281 nightly
The price is $318
Nov 16 - Nov 17
Total with taxes and fees
Private Apartment in Berlin
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

New Britain
10.0 out of 10, Exceptional, (7)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
$218 nightly
The price is $246
Nov 16 - Nov 17
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
HOMEY HOMEY

HOMEY HOMEY

Sixteen Acres
2.8 out of 10, (5)
"We checked out early. The place had mold/mildew. Power went out and the place was dark. Not suitable for human use without major renovations and updates."
United States
Shorayi M.
$147 nightly
The price is $167
Nov 15 - Nov 16
Total with taxes and fees
HOMEY HOMEY
Microwave, oven, stovetop, dishwasher
Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.

Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.

2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"Beautifully renovated and easy travels to many family and adult attractions locally. Parking is street side and we never had an issue parking our 2 vehicles out front of the home."
United States
Molly S.
Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.
Microwave, oven, stovetop
Cozy 2-bedroom apartment Near Six Flags & Attractions

Cozy 2-bedroom apartment Near Six Flags & Attractions

Forest Park
7.0 out of 10, Good, (2)
"The apartment is clean. Not the best of neighborhoods. Not a place I would walk around at night."
United States
Gary L.
Cozy 2-bedroom apartment Near Six Flags & Attractions
Fridge, microwave, oven, stovetop
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

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

Bloomfield
9.0 out of 10, Wonderful, (11)
"It was a comfortable stay "
United States
heidi L.
$534 nightly
The price is $605
Nov 17 - Nov 18
Total with taxes and fees
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Interior
Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements

Cromwell
$815 nightly
The price is $923
Nov 15 - Nov 16
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Fridge, microwave, stovetop, electric kettle
Modern Private Furnished Studio Downtown Hartford

Modern Private Furnished Studio Downtown Hartford

Downtown Hartford
4.0 out of 10, (1)
"Bed was uncomfortable, shower did not drain properly, shower ran out of hot water after a few minutes, and stove and TV did not work. Check-in was confusing: instructions for main acess was wrong."
United States
Jasmin S.
$135 nightly
The price is $152
Nov 16 - Nov 17
Total with taxes and fees
Modern Private Furnished Studio Downtown Hartford
TV
3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
Pine Point
9.6 out of 10, Exceptional, (7)
"The whole experience was great. The host was very nice and the place is comfy and enjoyable to stay at. Highly recommend. "
United States
Joel K.
3-bedroom house in perfect Springfield with WiFi, AC
Exterior
Beautiful retreat in a lake community to the enjoy the summer season.

Beautiful retreat in a lake community to the enjoy the summer season.

Tolland
10.0 out of 10, Exceptional, (44)
"It was a very nice home with a great sitting area. The screened in porch was another nice area."
United States
Susan D.
Beautiful retreat in a lake community to the enjoy the summer season.
Dining
The Serene Skyway Retreat

The Serene Skyway Retreat

Windsor Locks
8.8 out of 10, Excellent, (11)
"This home was perfect for my family, friends and I. Very accommodating and cozy. Quiet, safe location. close to stores and Bradley International Airport."
United States
Zarghona S.
$265 nightly
The price is $283
Nov 19 - Nov 20
Total with taxes and fees
The Serene Skyway Retreat
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Charming Chicopee Getaway

Chicopee
6.0 out of 10, (2)
"The apartment didn't look anything like the pictures. It was dingy and had a smell to it that we couldn't tolerate and that lingered in our nostrils for hours after we left. The kitchen area was unusable -- what passed for a table was at the same level as the chair seats, which made it impossible to use. Finally, we had to move a big trash bag full of trash out of the way before even being able to get in the door. We left within minutes after arriving and went to a hotel. "
United States
Kenneth M.
$222 nightly
The price is $259
Nov 17 - Nov 18
Total with taxes and fees
Charming Chicopee Getaway
Microwave
Cozy apartment in charming Hartford with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi

Downtown Hartford
9.0 out of 10, Wonderful, (7)
"Very nice for one night"
United States
Jack
$135 nightly
The price is $152
Nov 16 - Nov 17
Total with taxes and fees
Cozy apartment in charming Hartford with AC, WiFi
Interior
The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery

Plainville
8.8 out of 10, Excellent, (24)
"Pleasure staying here. "
United States
Jesse H.
$257 nightly
The price is $275
Nov 21 - Nov 22
Total with taxes and fees
The Sun Filled Cozy Creamery
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.
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Top Windsor Hotel Reviews

MGM Springfield

MGM Springfield

10/10 Excellent
"Room was clean and quiet. Staff was wonderful. Casino was clean."
Patricia 1-night trip
Posted 1 day ago
MGM Springfield

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, there are vacation rentals where you'll be just 13 mi (21 km) from Six Flags New England, providing a more remote option if you want peace and quiet. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What's the top vacation rental that Windsor has to offer?

Private Apartment in Berlin: This vacation home rental outside of Windsor is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Expedia has 6 vacation rentals for your stay in Windsor.

What can I see and do in Windsor?

Cultural attractions include Windsor Arts Center and Windsor Historical Society, whereas Keney Park and Northwest Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Loomis Chaffee School and Farmington River.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.