Windsor Holiday Rentals

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Holiday Rentals in Windsor

Paper towels
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, (2)
"This was easily accessible to many places and the check-in process and communications with the owner were exceptional. Great place to stay."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Fridge, microwave, oven, stovetop
A “Wow” Experience
8.0 out of 10, Very good, (1)
"We had a great stay at this property. Beds were very comfortable, which is not usually the case with many rentals. Good clean and hot showers and towels. Property had everything you need including a BBQ for grilling. My family of 6 was comfortable and plenty of room and space for everyone."
The price is NZ$950
per night
28 May - 29 May
A “Wow” Experience
Fridge, microwave, oven, stovetop
Bungalow House - Free Parking - 10 mins to Hartford & Airport
9.0 out of 10, Wonderful, (17)
"We were able to stay @ this location for several days just before the holidays. The space was perfect for the running around we needed to do and was a solid base of operation. The kitchen, bedroom, and bathroom are well-appointed. We did not spend any time in the living room or outside areas. The water pressure in the shower is amazing and I could spend hours there. :) The home is on a busy road at commute times so take the owner's advice and K turn in the driveway to make exiting the home...
The price is NZ$388
per night
29 May - 30 May
Bungalow House - Free Parking - 10 mins to Hartford & Airport
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Fridge, microwave, stovetop, dishwasher
Charming Windsor Home w/ Private Backyard!
Charming Windsor Home w/ Private Backyard!
Private kitchen
Beautiful Spacious Loft Style Townhome, 10 mins from train station and airport!
Beautiful Spacious Loft Style Townhome, 10 mins from train station and airport!
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
Microwave, oven, stovetop, dishwasher
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
4.0 out of 10, (1)
"Location has the potential to be great but it is run down and needs A LOT of work. From first walking in, refrigerator was so dirty/dusty you could run your finger down it and have a film on your hand. Wood flooring in kitchen area is warped because of an obvious leak in the ceiling. Ceiling in the kitchen has brown water stains in the ceiling, floor tiles in the upstairs bathroom are cracked, ants kept coming in from outside, food left in the fridge and trash was left in and on the garbage can,...
The price is NZ$379
per night
28 May - 29 May
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Fridge, microwave, oven, stovetop
PICON COZY
8.0 out of 10, Very good, (43)
"Fidelis demonstrated exceptional professionalism throughout our interaction. He was remarkably accommodating, consistently honest, and promptly addressed any inquiries I had, usually within minutes. On the rare occasion that he couldn't respond immediately, he took the time to provide an explanation and offer his apologies. Recently, my son relocated to this area for work, and thanks to Fidelis, I can now rest assured that my 24-year-old son, who has yet to experience living on his own, is safe...
The price is NZ$279
per night
30 May - 31 May
PICON COZY
Interior
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
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 NZ$1,165
per night
29 May - 30 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
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 NZ$558
per night
29 May - 30 May
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (120)
"Wonderful place! Thoughtfully decorated, clean and incredibly comfortable. Would rent again."
The price is NZ$594
per night
24 Jun - 25 Jun
Big farmhouse in the foothills of the Berkshires
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
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (18)
"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)
"Our week stay at the Bungalow was exactly what we needed to celebrate our 54th wedding anniversary. We were able to relax, disconnect, and enjoy the peacefulness of the setting by the lake. The bungalow is beautifully decorated and provided everything we could have wanted and more. We were impressed with the cleanliness, the comfortable beds and the special touches throughout. Lisa was a thoughtful and considerate exceptional host. She kept in touch when appropriate and offered helpful...
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Exterior
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, (106)
"Very nice stay. Only disappointment was the lack of a hot tub. Otherwise a perfect venue for our group."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
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
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, (1005)
"My niece really liked the breakfast provided. I liked the room. It was really spacious and clean. Parking was great and the staff was polite and helpful"
The price is NZ$241
per night
24 Jun - 25 Jun
HYATT house Hartford North/Windsor
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 NZ$239
per night
9 Jun - 10 Jun
Hilton Garden Inn Hartford North/Bradley Int'l Airport
49-inch Smart TV with digital channels, TV, Netflix
Marriott Hartford/Windsor Airport
3.5 star property
8.4 out of 10, Very good, (1002)
"The rooms were very clean"
The price is NZ$337
per night
1 Jun - 2 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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.

Recent reviews of Windsor properties
Expedia verified reviews