Windsor Vacation Rentals

Vacation Rentals in Windsor

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!
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 $300
$579 total
includes taxes & fees
Jun 11 - Jun 12
A “Wow” Experience
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 $107
$241 total
includes taxes & fees
Jun 12 - Jun 13
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!
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)
"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, (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 $75
$170 total
includes taxes & fees
Jun 10 - Jun 11
PICON COZY
Fun Downtown Location
9.8 out of 10, Exceptional, (49)
"Overall a good experience."
Fun Downtown Location
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 $183
$365 total
includes taxes & fees
Jun 9 - Jun 10
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, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
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, (15)
"Thank you for a lovely home to stay in during our family funeral weekend!"
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 $135
$304 total
includes taxes & fees
Jun 10 - Jun 11
Welcome to Honey Spot!
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
Beautiful retreat to the woods to enjoy the winter 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 to the woods to enjoy the winter season.
Thomas's Cozy Duplex - Centrally Located
8.0 out of 10, Very Good, (5)
"Enjoyed our weekend. Check in was easy, plenty of room for 4 adults. Good location near MGM/downtown Springfield."
The price is $110
$271 total
includes taxes & fees
Jun 11 - Jun 12
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 $220
$374 total
includes taxes & fees
Jul 8 - Jul 9
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
The getaway! Located in the downtown area.
10.0 out of 10, Exceptional, (7)
"This home was very nicely updated with new pillows, comfy bed and well stocked kitchen. Perfect location near the hospital"
The price is $157
$332 total
includes taxes & fees
Jul 2 - Jul 3
The getaway! Located in the downtown area.
Massive 5 Bedrooms: 3King 2Queen
The price is $354
$807 total
includes taxes & fees
Jun 11 - Jun 12
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."
The price is $100
$259 total
includes taxes & fees
Jun 18 - Jun 19
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
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 Vacation Rental Travel Info

Number of vacation rentals
3
Known landmarks
Xfinity Theatre, Connecticut Science Center 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, (1013)
"I had an amazing stay. I love the setup, look and feel of this hotel. The staff was welcoming and inviting. I will definitely stay here again."
The price is $137
$158 total
includes taxes & fees
Jun 26 - Jun 27
HYATT house Hartford North/Windsor
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3.0 star property
8.8 out of 10, Excellent, (1004)
"This property is great if you need a quiet, near the airport hotel.. Thanks"
The price is $127
$146 total
includes taxes & fees
Jun 16 - Jun 17
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Marriott Hartford/Windsor Airport
3.5 star property
8.6 out of 10, Excellent, (1001)
"The hotel is super clean. Easy quick check in very welcoming. "
The price is $179
$206 total
includes taxes & fees
Jul 1 - Jul 2
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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 vacation rentals in Windsor?

Yes, there are vacation rentals where you'll be just 13 mi (21 km) from Six Flags New England, providing a more remote option if you want peace and quiet. Visitors like the top-notch restaurants and shops in Windsor. Allow some time to check out the theme park during your trip.

What's the top vacation rental that Windsor has to offer?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This highly rated vacation home rental in Windsor has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Windsor?

Expedia has 7 vacation 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 vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

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