Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Island Vibes Home

10.0 out of 10, Exceptional, (8)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

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

9.0 out of 10, Wonderful, (2)
"Great property and a great location. The host was more than welcoming and very easy to communicate to. This was our second visit to this location and we plan to stay again if availability allows. "
The price is €561
includes taxes & fees
2 Dec - 3 Dec
A “Wow” Experience everywhere there is something to stimulate your mind Interest

Bungalow House - Free Parking - 10 mins to Hartford & Airport

8.0 out of 10, Very good, (22)
"House was very clean. Everything was as described and the Owner was very responsive to our requests pre checkin."
Bungalow House - Free Parking - 10 mins to Hartford & Airport

Charming Windsor Home w/ Private Backyard!

8.0 out of 10, Very good, (2)
"This was the perfect location to celebrate graduation and enjoy time with family. It is an older home, but had plenty of room and nice central location. Beautiful flowers in front, peaceful backyard, thank you for sharing your home!"
Charming Windsor Home w/ Private Backyard!

136 Raymond · Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (20)
"Immaculate Victorian home wonderfully renovated for modern convenience. Perfect Location; easy on/off Interstate 84. Gracious host who was ultra responsive. Very pleasant stay. "
136 Raymond · Prime West Hartford Center Location: Historic Gem

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!

Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks

9.0 out of 10, Wonderful, (36)
"Wonderful host. Very thoughtful - lots provided in the house that you need to have a great stay. "
The price is €274
includes taxes & fees
2 Dec - 3 Dec
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is €168
includes taxes & fees
2 Dec - 3 Dec
PICON COZY

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

9.2 out of 10, Wonderful, (20)
"Brought the kids and grandkids to six flags. This rental was a short drive. We had a group of eight and everyone had plenty of room. The place was clean stocked and as advertised. If we are ever in the area again we will definitely stay again. "
The price is €534
includes taxes & fees
26 Nov - 27 Nov
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is €352
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (47)
"What a gem this cute house was on the lake! The owners didn’t skip a beat with the attention to detail. It had everything and was so clean. Communication was spot on. We will definitely book again the next time we come to CT! We already miss waking up with coffee and watching the sun come up over the lake. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (65)
"This property is a remodeled older house. With all that old house charm. It is spacious and has three bedrooms, each with a queen bed. The couch is extremely comfortable and it was great watching TV and sipping wine."
Fun Downtown Location 2nd flr

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very good, (8)
"Eunice was great to work with, and the place was fantastic for our family of four going to six flags."
The price is €267
includes taxes & fees
26 Nov - 27 Nov
Thomas's Cozy Duplex - Centrally Located

Exquisite Downtown Loft Apartment

8.0 out of 10, Very good, (6)
"Will stay again"
Exquisite Downtown Loft Apartment

Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

10.0 out of 10, Exceptional, (61)
"Went to the Big E for a few days, great location, 10-15 minute ride to the fair. Was perfect to come back and relax after a long day at the fair. Home was very clean and updated. Communication was great. Could use some pans that work with the cooktop. The bathroom setup was a little strange, you have to walk throught the master bedroom to get to the bathroom, so the second bedroom guest had to walk through our bedroom in the middle of the night to use the restroom. Ad states Oven, hot tub,...
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"Very nice and clean. Great location for proximity to our family"
Linny's Updated Lakeview Cottage - Cozy & Modern

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
River Overlook - Check the view from your deck!

Tastefully furnished repose home

6.0 out of 10, (3)
"The neighborhood is not safe at all. "
Tastefully furnished repose home
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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Other types of properties in Windsor you may be interested in

HYATT house Hartford North/Windsor

3.0 star property
9.0 out of 10, Wonderful, (1078)
"Nice staff, really helpful when I needed to get some documents printed."
The price is €112
includes taxes & fees
2 Dec - 3 Dec
HYATT house Hartford North/Windsor

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3.0 star property
8.8 out of 10, Excellent, (1063)
"Nice place. Gym was lacking. Staff is terrific. Nice balcony but all around the place is parking lot. "
The price is €130
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Marriott Hartford/Windsor Airport

3.5 star property
8.4 out of 10, Very good, (1043)
"The room was nice, the bed was very comfortable! The carpets throughout the hotel were refreshingly, very clean. The breakfast buffet was very good, and the staff was great. Our waitress, Nancy, was absolutely amazing! She took care of us and all of her guests, as if we were family! She loves her job and it shows. She’s a great representative of the company and the level of care she puts into her job is why people stay at Marriott hotels around the world! Great job Nancy!! "
The price is €164
includes taxes & fees
6 Dec - 7 Dec
Marriott Hartford/Windsor Airport
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.

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?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This highly rated holiday home rental in Windsor has air conditioning and WiFi 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 Farmington River and Northwest Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include SS&C SummerWind Performing Arts Center and Vintage Radio and Communications Museum of Connecticut.

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.