Holiday Rentals in Windsor

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Holiday Rentals in Windsor

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.6 out of 10, Exceptional, (4)
"The location was great to get to and from the airport. Lynn was great with responding to any of my questions. We would stat again when visiting family."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
A “Wow” Experience everywhere there is something to stimulate your mind Interest
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."
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Bungalow House - Free Parking - 10 mins to Hartford & Airport
9.0 out of 10, Wonderful, (18)
"House was very clean. Everything was as described and the Owner was very responsive to our requests pre checkin."
The price is €233
per night
26 Jun - 27 Jun
Bungalow House - Free Parking - 10 mins to Hartford & Airport
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Charming Windsor Home w/ Private Backyard!
10.0 out of 10, Exceptional, (1)
"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!
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
PICON COZY
8.0 out of 10, Very good, (44)
"Perfect little house 20 minutes from six flags. Bathroom looks like it was recently updated as well as kitchen appliances. it's a little dated but who cares the price was right. Much more relaxing and comfy than a hotel room."
The price is €163
per night
2 Jul - 3 Jul
PICON COZY
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, (51)
"Great property for our family trip. We had lots of fun. Owner was responsive and communicative. Hope to be back some day!"
Fun Downtown Location 2nd flr
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.6 out of 10, Exceptional, (26)
"Great place, very clean, and as described! Thanks for a great experience!"
The price is €384
per night
21 Jul - 22 Jul
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
10.0 out of 10, Exceptional, (3)
"Everything from check in to check out was a breeze. The house is clean, cozy and comfortable. Managers are very responsive and kind. We needed to extend our stay due to a medical issue, they were very gracious and were happy to help anyway possible. I would most definitely book again. Only thing i would like to share is the flight of stairs to get to main floor of the house could be difficult for some people, just keep that in mind. We were fine with it and were traveling with my mother in law...
Spacious three bedroom house with pool and hot tub near Historic Suffield Center
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (17)
"We enjoyed meeting and spending time with all the lovely animals on this quaint farm. Apartment was so lovely and spacious. Highly recommend stopping by for a stay."
Mountaintop Horse Farm with Heated Pool
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Welcome to Honey Spot!
10.0 out of 10, Exceptional, (24)
"We loved this property! Had everything we needed and we didn't have time to use or enjoy everything. The beds were SO COMFY!!! Loved having 2 bathrooms also. Great communication with the host! We would love to come back!"
The price is €291
per night
2 Jul - 3 Jul
Welcome to Honey Spot!
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, (107)
"A number of friends and I stayed here to be nearby our friends wake and memorial service. It was a really nice homely, quiet space that had plenty of room for everyone and the view over the river is gorgeous. Would love to come back sometime for more uplifting circumstances"
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Beautiful retreat in a lake community to the enjoy the summer season.
10.0 out of 10, Exceptional, (31)
"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."
Beautiful retreat in a lake community to the enjoy the summer season.
Thomas's Cozy Duplex - Centrally Located
8.4 out of 10, Very good, (6)
"Cute place, nice neighbors"
The price is €244
per night
22 Jul - 23 Jul
Thomas's Cozy Duplex - Centrally Located
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, (8)
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is €286
per night
15 Jul - 16 Jul
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
The getaway! Located in the downtown area.
9.0 out of 10, Wonderful, (8)
"This home was very nicely updated with new pillows, comfy bed and well stocked kitchen. Perfect location near the hospital"
The price is €259
per night
9 Jul - 10 Jul
The getaway! Located in the downtown area.
Massive 5 Bedrooms: 3King 2Queen
The price is €778
per night
9 Jul - 10 Jul
Massive 5 Bedrooms: 3King 2Queen
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
7.0 out of 10, Good, (2)
"We enjoyed our stay at this home. It was clean, beds were comfy and it was spacious. One small thing was that there was only one tv and it did not work."
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (8)
"We were there for a family event in Glastonbury for just a couple of days, and so we didn't go to the lake. However, the cottage was perfect for our needs -- quiet, allowed for contemplation, and privacy that we needed. We hope to perhaps and experience the beautiful lake."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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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

HYATT house Hartford North/Windsor
3.0 star property
9.0 out of 10, Wonderful, (1005)
"Loved everything about it, wished we could have stayed longer"
The price is €153
per night
7 Jul - 8 Jul
HYATT house Hartford North/Windsor
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3.0 star property
8.8 out of 10, Excellent, (999)
"Wasn’t aware that the pool is no longer open and with kids that made it hard . "
The price is €136
per night
1 Jul - 2 Jul
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Marriott Hartford/Windsor Airport
3.5 star property
8.4 out of 10, Very good, (1000)
"It was pretty clean; there was something going on with the shower the floor got soaking wet and the air conditioning was a little wonky."
The price is €192
per night
3 Jul - 4 Jul
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.

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €163 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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