Windsor Holiday Rentals

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Holiday Rentals in Windsor

Fridge, microwave, oven, stovetop
Island Vibes Home
10.0 out of 10, Exceptional, (2)
"House was nice. It had a lot of character. Updated kitchen and bathrooms. Loved the grand piano, and stained glass window and light in the hallway. Neighborhood was quiet and yard was nice. There is a walking trail right next to the house that cuts through to the local high school. I would recommend as a nice comfortable place to stay."
Island Vibes Home
Fridge, microwave, oven, stovetop
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
The price is HK$2,340
per night
24 May - 25 May
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
Outdoor pool, a heated pool
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (15)
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
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Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (119)
"My wife and I and our daughter and dog spent the week. Everything we needed was provided. Nice quiet and relaxing time. Great location down the street from the AMC Noble View trails. We all had a wonderful hike and a wonderful week."
The price is HK$1,677
per night
22 May - 23 May
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (17)
"The property was perfect for our needs. Instructions for everything was provided fabulous rental. "
Newly Renovated Family House On Highland Lake with Dock
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (7)
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Property grounds
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
10.0 out of 10, Exceptional, (6)
"excellent"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
Property grounds
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
10.0 out of 10, Exceptional, (28)
"We booked this for my son’s UConn graduation.My family of 4 stayed and it was perfect!! The Bungalow is clean and meticulously decorated! We felt so at home and it had everything we needed. All the nice touches like water and complimentary bag were very generous. I would definitely recommend to all!"
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Property grounds
Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
10.0 out of 10, Exceptional, (31)
"We had a lovely weekend celebrating our son’s graduation from UConn. The Panorama was immaculate with beautiful decor and the most comfortable beds. The view of the lake is stunning. Everything was just perfect. I hope we have a reason to come back one day!"
Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
Interior
River Overlook - Check the view from your deck!
10.0 out of 10, Exceptional, (8)
"The location was just as promised. The view on the deck is beautiful and the apartment was clean and well stocked with anything you might need. The location is also walking distance to various shops, pizza, restaurants and bars. The river walk across the street is also great if you want to take a stroll. Carol was also great to work with. We’ll be back."
River Overlook - Check the view from your deck!
Microwave, oven, stovetop, dishwasher
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
10.0 out of 10, Exceptional, (2)
"My family and I enjoyed our stay here. We had lots of space for my 4yo to run around and each of my 3 kids had their own room. The house was very clean and the host was easily able to contact if I had questions or concerns. We would def. stay here again"
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Fridge, microwave, oven, stovetop
Upscaled Quiet Neighborhood- Modern 3 BDRM
10.0 out of 10, Exceptional, (20)
"Enjoyed our stay very much. We definitely recommend and stay again in near future. Management was quick with response and very helpful and kind."
Upscaled Quiet Neighborhood- Modern 3 BDRM
Property grounds
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
10.0 out of 10, Exceptional, (6)
"From the very beginning the hosts were fantastic. There was great communication and offered support. The property was super clean , well organized, and perfect for what we needed. I will be staying here again and truly recommend it !"
The price is HK$1,786
per night
28 May - 29 May
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Fridge, microwave, oven, stovetop
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
10.0 out of 10, Exceptional, (56)
"The place was nice and is clean. I knew it was a downstairs of a house. The owner does have a dog that barks from time to time in the evening and you can hear people above, but was not too much to handle. Overall was a nice place in a nice town."
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (47)
"Host was amazing 5 star all the way ... we walked right down the street and had some pizza everything we needed was just around the corner."
Fun Downtown Location
TV, DVD player, books, video library
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
9.8 out of 10, Exceptional, (44)
"Great experience over all. Would definitely recommend this cottage on the lake. Communication, check in, over all experience was great! Highly recommend!"
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
Fridge, microwave, oven, stovetop
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.6 out of 10, Exceptional, (24)
"Joe was very attentive and left the house very clean for us. Definitely worth the money"
The price is HK$1,350
per night
28 May - 29 May
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
Dining
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
9.6 out of 10, Exceptional, (28)
"It was nice stay!"
The price is HK$1,419
per night
2 Jun - 3 Jun
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.4 out of 10, Exceptional, (33)
"Very positive."
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Fridge, microwave, oven, stovetop
comfortable home away from home
9.2 out of 10, Wonderful, (5)
"This little house is tucked behind some bigger neighbors. It was comfortable and quiet! We had a ball watching the antics of a family of squirrels. It fit our needs perfectly!"
comfortable home away from home
Don't see what you're looking for?
See all available properties in Windsor
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.

Other types of properties in Windsor you may be interested in

Lobby sitting area
HYATT house Hartford North/Windsor
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Very friendly and helpful staff."
The price is HK$920
per night
29 May - 30 May
HYATT house Hartford North/Windsor
BBQ/picnic Area
Courtyard By Marriott Hartford/Windsor Airport
3.0 star property
9.0 out of 10, Wonderful, (947)
"Very friendly staff and clean rooms. "
The price is HK$1,256
per night
14 Jun - 15 Jun
Courtyard By Marriott Hartford/Windsor Airport
Meeting facility
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3.0 star property
8.8 out of 10, Excellent, (999)
"Overall a great team, great customer service except when we first arrived and checked in."
The price is HK$955
per night
27 May - 28 May
Hilton Garden Inn Hartford North/Bradley Int'l 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.

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 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?

The Bungalow at Eagleville Lake Under 3 miles to UCONN! : This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Windsor?

Expedia has 6 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 Vintage Radio and Communications Museum of Connecticut and Oliver Ellsworth Homestead.

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.

Recent reviews of Windsor properties
Expedia verified reviews

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

5/5 Excellent
"Very friendly and helpful staff."
A verified traveller stayed at HYATT house Hartford North/Windsor
Posted 21 hours ago
HYATT house Hartford North/Windsor