Search Vacation Homes in Windsor

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 176 Vacation Homes in Windsor with updated reviews, rates, and availability.

Island Vibes Home

10.0 out of 10, Exceptional, (10)
"The home was clean and well cared for, and had everything we needed. The location was perfect for every where we wanted to go. We had shopping near by to keep us in groceries, and we had easy access to roads to get us to/from area sites and attractions. The one snow day we had, someone came and cleared the walkways and driveway so we didn't have to, that was a nice surprise, and they even rolled the garbage can out and back on pick up day. "
Island Vibes Home

15mins to Hartford, Home in Manchester w/ King Bed

2.0 star property
7.0 out of 10, Good, (2)
"We stay in rental all the time. This was definitely the worst that we have ever seen. There was no booklet of information left to give you instructions for the house. There were no labels on switches, instructions on how to use the fireplace, photograph of the supplies in the kitchen were not the same as what you Experienced. Made it very difficult to cook, so we just didn’t. The pots and pans were old and scratched, and not the kind of thing that anybody should be using and they should be...
15mins to Hartford, Home in Manchester w/ King Bed

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (1)
"Enjoyed one night in this 3Br property. It was comfortable, secure and easy to locate. Great parking, kitchen, tv and wash/dry facilities. Would recommend."
The price is SAR 492
SAR 1,118 total
includes taxes & fees
20 Jan - 21 January 2025
Beautiful 3BR, Rare Find, Clean & Guest Favorite

PICON COZY

7.8 out of 10, Good, (55)
"Todo limpio y con buena ubicacion"
The price is SAR 282
SAR 639 total
includes taxes & fees
2 Jan - 3 January 2025
PICON COZY

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (129)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is SAR 808
SAR 1,433 total
includes taxes & fees
29 Dec - 30 Dec
Big farmhouse in the foothills of the Berkshires

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.6 out of 10, Exceptional, (11)
"Our visit at this VRBO was almost excellent… the only issue we had was with theTVs. We could not get the TVs in the bedroom to work. Cleanliness was exceptional! Availability of food/meal supplies was great. It was nice that there was ice already made for us. The towel and wash cloths were fluffy and absorbent. The queen bed and pillows were very comfortable. We cannot say there was anything that did not meet expectations! Anyone would be comfortable there. We would book again. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
The price is SAR 1,427
SAR 2,575 total
includes taxes & fees
28 Dec - 29 Dec
A “Wow” Experience everywhere there is something to stimulate your mind Interest

Cozy newly remodeled home close to major amenities in Connecticut a

8.4 out of 10, Very Good, (17)
"I love staying here. Each visit I bring something new from Louisiana and leave it for the next guest. The cooking supplies are admirable for a home, and especially so for a home away-from-home. We couldn't find a better place to stay. The beds are super comfy, though the furniture requires extra padding. Fortunately there are lots of blankets to use as cishioning."
Cozy newly remodeled home close to major amenities in Connecticut a

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (55)
"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"
Linny's Updated Lakeview Cottage - Cozy & Modern

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

8.4 out of 10, Very Good, (6)
"I was a bit nervous after booking and ready some of the reviews about being a noisy location as I’m a light sleeper. It is a very active neighborhood directly behind large shopping with a railroad track nearby and a flight path directly overhead. However I just played some white noise music on my phone and it was fine. We didn’t spend much time at the house as we were on business leaving around 5am daily and coming back after 9pm. It’s too bad because it has a huge nice backyard. Plenty of off...
The price is SAR 376
SAR 1,095 total
includes taxes & fees
26 Dec - 27 Dec
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Grammy's Lake House w/ Private Waterfront Access

9.8 out of 10, Exceptional, (8)
"We enjoyed our time at the cottage. We had an air conditioning issue when we arrived, and Niles took care of it by the next day. We did not spend a lot of time there because we were with family, but we had everything we needed."
Grammy's Lake House w/ Private Waterfront Access

The Lake House

9.8 out of 10, Exceptional, (8)
"Wonderful place to camp for a large family, particularly in summertime. Great view of the lake and the best sunsets. "
The Lake House

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (7)
"Very enjoyable weekend. Summer coming to an end so crisp mornings and pool water a little cold. Farm animals fun for children’s entertainment. Host was a great historian for the area."
Charming Farmhouse w/ Pool & Fishing Pond!

Linny’s Cozy Lakeside Family Friendly Home with dock

9.8 out of 10, Exceptional, (18)
"Cozy little cottage for peace and relaxation. "
Linny’s Cozy Lakeside Family Friendly Home with dock

Spacious Tolland Home w/ Deck + Screened Porch!

9.6 out of 10, Exceptional, (4)
"Great communication; well supplied home; beautiful and peaceful surroundings; some items in need of repair; lovely stay overall"
Spacious Tolland Home w/ Deck + Screened Porch!

Stylish & Luxurious 3 BDR Home with Play Station

9.8 out of 10, Exceptional, (7)
"We had an issue getting into the house, but the host answered the phone immediately and helped us gain access. His communication was excellent. We chose this location because of the proximity to our family and it worked out perfectly."
Stylish & Luxurious 3 BDR Home with Play Station

Beautiful Luxury 2 Bedroom

Beautiful Luxury 2 Bedroom

The Congamond Cottages: Private Lakefront Cottage

8.4 out of 10, Very Good, (5)
"This was the perfect place to stay during the big E. It was very peaceful and helpful during the bustle of the fair. We hope to book again next year."
The Congamond Cottages: Private Lakefront Cottage
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windsor

Island Vibes Home

10.0 out of 10, Exceptional, (10)
"The home was clean and well cared for, and had everything we needed. The location was perfect for every where we wanted to go. We had shopping near by to keep us in groceries, and we had easy access to roads to get us to/from area sites and attractions. The one snow day we had, someone came and cleared the walkways and driveway so we didn't have to, that was a nice surprise, and they even rolled the garbage can out and back on pick up day. "
Island Vibes Home

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.6 out of 10, Exceptional, (11)
"Our visit at this VRBO was almost excellent… the only issue we had was with theTVs. We could not get the TVs in the bedroom to work. Cleanliness was exceptional! Availability of food/meal supplies was great. It was nice that there was ice already made for us. The towel and wash cloths were fluffy and absorbent. The queen bed and pillows were very comfortable. We cannot say there was anything that did not meet expectations! Anyone would be comfortable there. We would book again. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
The price is SAR 1,427
SAR 2,575 total
includes taxes & fees
28 Dec - 29 Dec
A “Wow” Experience everywhere there is something to stimulate your mind Interest
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.