Windsor Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Windsor

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
Charming Windsor Home w/ Private Backyard!
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!
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 HK$926
HK$1,355 total
includes taxes & fees
13 Oct - 14 Oct
Cozy apartment in charming Hartford with AC, WiFi
Lux Boutique Large Private LOFT Pratt St Hartford
Iron/ironing board, WiFi, bed sheets

Lux Boutique Large Private LOFT Pratt St Hartford

8.4 out of 10, Very good, (21)
"Location was great. Lots of things to do and many nearby options for eating and drinks. View was disappointing—dark and one window facing a brick wall. Biggest complaint was neighbors and noise—first two nights there was loud music and parties until early morning hours."
The price is HK$848
HK$1,265 total
includes taxes & fees
13 Oct - 14 Oct
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 HK$817
HK$1,230 total
includes taxes & fees
13 Oct - 14 Oct
Totally Private Cozy studio in awesome Hartford with WiFi, AC
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
3 bedrooms, iron/ironing board, WiFi, bed sheets

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

5.4 out of 10, (3)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
The price is HK$1,323
HK$1,693 total
includes taxes & fees
16 Oct - 17 Oct
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
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

9.6 out of 10, Exceptional, (4)
"Cozy, clean, comfortable. Location is excellent and accessible to restaurants and venues. Highly recommended. "
The price is HK$817
HK$1,566 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Newly Renovated 2 floor Getaway
Full-sized fridge, microwave, oven, dishwasher

Newly Renovated 2 floor Getaway

3.5 star property
The price is HK$3,565
HK$5,212 total
includes taxes & fees
12 Oct - 13 Oct
Newly Renovated 2 floor Getaway
Enjoyable and Spacious 3 bedroom apartment in Springfield
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Enjoyable and Spacious 3 bedroom apartment in Springfield

Enjoyable and Spacious 3 bedroom apartment in Springfield
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, (26)
"Check in was easy. This met all of our needs. "
The price is HK$2,950
HK$5,342 total
includes taxes & fees
17 Oct - 18 Oct
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
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. "
The price is HK$910
HK$2,459 total
includes taxes & fees
13 Oct - 14 Oct
Private Apartment in Berlin
Cozy Safe Home
Fridge, microwave, oven, stovetop

Cozy Safe Home

The price is HK$1,807
HK$3,058 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Safe Home
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 HK$560
HK$1,298 total
includes taxes & fees
15 Oct - 16 Oct
HOMEY HOMEY
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
The price is HK$864
HK$1,928 total
includes taxes & fees
12 Oct - 13 Oct
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
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 HK$1,136
HK$2,248 total
includes taxes & fees
3 Nov - 4 Nov
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
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 HK$3,572
HK$4,573 total
includes taxes & fees
19 Oct - 20 Oct
Charming 3 bed/2 bath town home with gorgeous back yard
Stylish Downtown Business| Hospital | WD | GYM
TV

Stylish Downtown Business| Hospital | WD | GYM

8.6 out of 10, Excellent, (4)
"Central to everything in downtown Hartford! "
The price is HK$895
HK$1,940 total
includes taxes & fees
12 Oct - 13 Oct
Stylish Downtown Business| Hospital | WD | GYM
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 HK$1,296
HK$2,653 total
includes taxes & fees
10 Oct - 11 Oct
Newly Beautiful renovated first floor apartment getaway
Conference Room Rental no sleeping arrangements
Interior

Conference Room Rental no sleeping arrangements

The price is HK$5,603
HK$7,175 total
includes taxes & fees
10 Oct - 11 Oct
Conference Room Rental no sleeping arrangements
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 HK$554
HK$1,291 total
includes taxes & fees
23 Oct - 24 Oct
PICON COZY
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"We had a great room with a beautiful view of the Hartford Capital! Room was ckean and comfortable and clean. Staff was friendly. Would recommend. "
Mary 1-night trip
Posted 3 days ago
The Capitol Hotel

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Windsor?

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

What are some of the best holiday rentals that Windsor has to offer?

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay: This holiday home rental outside of Windsor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Windsor?

Expedia has 7 holiday 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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.