Windsor Vacation Rentals

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In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Windsor

Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very Good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (8)
"We had a very nice time and the house is charming"
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

8.8 out of 10, Excellent, (19)
"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."
The price is ￥17,566
￥25,699 total
includes taxes & fees
Sep 25 - Sep 26
Lux Boutique Large Private LOFT Pratt St Hartford
Totally Private Cozy studio in awesome Hartford with WiFi, AC
WiFi, bed sheets

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.2 out of 10, Wonderful, (10)
"Great!"
The price is ￥16,975
￥25,020 total
includes taxes & fees
Sep 28 - Sep 29
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Cozy apartment in charming Hartford with AC, WiFi
Microwave

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (3)
"All was as advertised. The Xfinity INDOOR theatre us across the the street. Xfinity OUTDOOR theatre/ arena is only about a .8 mile walk away. We took an UBER there and walked back after our concert"
The price is ￥17,566
￥25,699 total
includes taxes & fees
Oct 1 - Oct 2
Cozy apartment in charming Hartford with AC, WiFi
New Furnished Apt in West Hartford w/ Parking and Central AC
Microwave, oven, stovetop, coffee/tea maker

New Furnished Apt in West Hartford w/ Parking and Central AC

6.8 out of 10, (3)
"Good communication with the manager, quiet place and extremely clean. I enjoyed it"
The price is ￥10,849
￥27,312 total
includes taxes & fees
Oct 1 - Oct 2
New Furnished Apt in West Hartford w/ Parking and Central AC
HOMEY HOMEY

HOMEY HOMEY

3.0 out of 10, (4)
"We did not even stay. The upstairs has access to the basement door so I did not at all feel comfortable. And there is a terrible mildew smell. "
The price is ￥10,628
￥24,617 total
includes taxes & fees
Oct 6 - Oct 7
HOMEY HOMEY
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Smart TV, fireplace, video games, books

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

9.8 out of 10, Exceptional, (36)
"Very clean, good host, well stocked kitchen, good location in Springfield, good beds and bathrooms, quiet. Living room and dining room have very unusual dramatic red furniture and a throne chair, but we enjoyed the eccentric touch. "
The price is ￥25,942
￥45,006 total
includes taxes & fees
Sep 30 - Oct 1
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
TV

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

10.0 out of 10, Exceptional, (5)
The price is ￥20,827
￥41,824 total
includes taxes & fees
Sep 28 - Sep 29
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Newly Beautiful renovated first floor apartment getaway
Fridge, microwave, oven, stovetop

Newly Beautiful renovated first floor apartment getaway

8.0 out of 10, Very Good, (2)
"We had an amazing time. This property was easy to find and very close to aloy of restaurants and shops! We had amazing chinese food! The apartment felt very homey. I love that it wasnt echo-y like past places I have stayed! I met Rose, the host, and she was super nice. She was very responsive and explained everything I needed to know before I arrived at the property. Also she lives near by and can address any problems or concerns you may have. The photography on the walls were gorgeous, the...
The price is ￥24,577
￥50,325 total
includes taxes & fees
Oct 1 - Oct 2
Newly Beautiful renovated first floor apartment getaway
3-bedroom house in perfect Springfield with WiFi, AC
TV

3-bedroom house in perfect Springfield with WiFi, AC

2.0 star property
9.2 out of 10, Wonderful, (5)
"Every question we had was quickly answered. The house was comfortable for us. Only a small hiccup in getting the door to lock when we left."
3-bedroom house in perfect Springfield with WiFi, AC
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Fridge, microwave, oven, stovetop

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

9.0 out of 10, Wonderful, (25)
"Check in was easy. This met all of our needs. "
The price is ￥55,952
￥101,324 total
includes taxes & fees
Oct 1 - Oct 2
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Cozy Safe Home
Fridge, microwave, oven, stovetop

Cozy Safe Home

The price is ￥25,906
￥48,244 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Safe Home
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Microwave, electric kettle, cookware/dishes/utensils, paper towels

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

10.0 out of 10, Exceptional, (3)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
The price is ￥17,566
￥32,083 total
includes taxes & fees
Sep 25 - Sep 26
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
The price is ￥14,466
￥40,779 total
includes taxes & fees
Sep 30 - Oct 1
Charming Chicopee Getaway
Conference Room Rental no sleeping arrangements
Interior

Conference Room Rental no sleeping arrangements

The price is ￥106,279
￥136,982 total
includes taxes & fees
Sep 25 - Sep 26
Conference Room Rental no sleeping arrangements
Charming 3 bed/2 bath town home with gorgeous back yard
Property grounds

Charming 3 bed/2 bath town home with gorgeous back yard

9.8 out of 10, Exceptional, (12)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
The price is ￥67,753
￥85,239 total
includes taxes & fees
Sep 25 - Sep 26
Charming 3 bed/2 bath town home with gorgeous back yard
PICON COZY
Smart TV

PICON COZY

7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is ￥11,071
￥25,121 total
includes taxes & fees
Oct 20 - Oct 21
PICON COZY
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (60)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is ￥42,659
￥72,417 total
includes taxes & fees
Oct 8 - Oct 9
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fully Furnished Private Loft Style Charm Trumbull Elevator
Private kitchen

Fully Furnished Private Loft Style Charm Trumbull Elevator

7.0 out of 10, Good, (2)
"Great place to stay. Lots of room compared to a hotel room and it's nice to have the kitchen area. We used the bonus spaces a lot and found the building to be very quiet from room to room. The noise from outside at night was mostly car noise and seemed pretty standard for being in a central location. Thank you!"
The price is ￥17,566
￥32,083 total
includes taxes & fees
Sep 28 - Sep 29
Fully Furnished Private Loft Style Charm Trumbull Elevator
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"A close, convenient and comfortable option when attending the Big E. "
John 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!: This vacation home rental outside of Windsor is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Windsor?

Expedia has 7 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.