Windsor Holiday Rentals

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Holiday Rentals in Windsor

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, 2 reviews
"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!
A “Wow” Experience
8.0 out of 10, Very good, 1 review
"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 AU$884
includes taxes & fees
6 June - 7 June
A “Wow” Experience
Bungalow House - Free Parking - 10 mins to Hartford & Airport
9.0 out of 10, Wonderful, 17 reviews
"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 AU$366
includes taxes & fees
12 June - 13 June
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 review
"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!
Beautiful Spacious Loft Style Townhome, 10 mins from train station and airport!
Beautiful Spacious Loft Style Townhome, 10 mins from train station and airport!
Island Vibes Home
10.0 out of 10, Exceptional, 2 reviews
"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
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, 2 reviews
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
Fun Downtown Location
9.8 out of 10, Exceptional, 48 reviews
"Nice space with 3 roomy bedrooms. Plenty of storage for clothes. Bathroom is small but not untypical of this era home. Steps to second floor are steep, so consider this. Kitchen has what you need for a short stay."
Fun Downtown Location
PICON COZY
8.0 out of 10, Very good, 43 reviews
"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 AU$259
includes taxes & fees
2 June - 3 June
PICON COZY
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, 15 reviews
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.6 out of 10, Exceptional, 25 reviews
"Joe was very attentive and left the house very clean for us. Definitely worth the money"
The price is AU$542
includes taxes & fees
3 June - 4 June
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, 106 reviews
"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
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, 8 reviews
"Beautiful, quiet, private yet convenient setting, perfect room setup and accommodations/amenities, along with a gracious and helpful host. Based on my stay experience, I would recommend this property unconditionally and look forward to a longer stay in the future. Thanks!"
The price is AU$580
includes taxes & fees
30 June - 1 July
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Massive 5 Bedrooms: 3King 2Queen
The price is AU$1,240
includes taxes & fees
5 June - 6 June
Massive 5 Bedrooms: 3King 2Queen
Welcome to Honey Spot!
10.0 out of 10, Exceptional, 24 reviews
"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 AU$464
includes taxes & fees
3 June - 4 June
Welcome to Honey Spot!
Privacy, entertainment, comfort galore 2 BR LR 1BA Home Theater, Pool Table
10.0 out of 10, Exceptional, 56 reviews
"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
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, 7 reviews
"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!
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
7.0 out of 10, Good, 2 reviews
"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 AU$355
includes taxes & fees
2 June - 3 June
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
lakefront estate
3.8 out of 10, 8 reviews
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
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.

Windsor Holiday Home Travel Info

Number of holiday homes
3
Known landmarks
Xfinity Theatre, Connecticut Science Centre and Nomads Adventure Quest
International airport
Hartford, CT (BDL-Bradley Intl.)

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, 1,005 reviews
"Returned to this hotel because how nice it is"
The price is AU$183
includes taxes & fees
1 July - 2 July
HYATT house Hartford North/Windsor
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3.0 star property
8.8 out of 10, Excellent, 1,001 reviews
"Always stay here when i have a flight out of hartford. They offer extended parking and free shuttle to the airport"
The price is AU$219
includes taxes & fees
9 June - 10 June
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Marriott Hartford/Windsor Airport
3.5 star property
8.6 out of 10, Excellent, 1,003 reviews
"Clean hotel, nice restaurant and bar area, clean rooms, soft bed. Pool is small but nice, good fitness center"
The price is AU$309
includes taxes & fees
1 July - 2 July
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, 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 favourite 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 depend 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 AU$259 per night. Entering your travel dates in the search wizard might find you 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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Expedia verified reviews