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Compare 162 Vacation Homes in Windsor with updated reviews, rates, and availability.

Charming 2-bedroom townhome
Room

Charming 2-bedroom townhome

2.0 star property
9.6 out of 10, Exceptional, (5)
"The home was beautiful and I would stay there again."
The price is AED 533
AED 806 total
includes taxes & fees
27 Nov - 28 Nov
Charming 2-bedroom townhome
Historic Farmhouse Near Mountains & Colleges!
Westfield Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (3)
"A group of us traveled quite a distance and were so happy to see the great place for us to stay. The house was beautifully restored and tastefully decorated. We felt at home immediately. There were enough room for all of us to spread out and do work or school studies without interrupting others and the back yard was big enough for the kids to blow off steam. The enclosed sunroom was the most popular room in the entire place. This place was top notch! Absolutely perfect!!"
Historic Farmhouse Near Mountains & Colleges!
PICON COZY
Private kitchen

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is AED 275
AED 625 total
includes taxes & fees
2 Dec - 3 Dec
PICON COZY
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beautiful 5BR Lake House on Highland Lake

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

10.0 out of 10, Exceptional, (90)
"Beautiful spot on the lake. Great house. "
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
15mins to Hartford, Home in Manchester w/ King Bed
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very spacious location. Ideal fit for our plans. "
The price is AED 687
AED 1,359 total
includes taxes & fees
3 Dec - 4 Dec
15mins to Hartford, Home in Manchester w/ King Bed
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Kitchen

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (29)
"It was nice stay!"
The price is AED 687
AED 1,171 total
includes taxes & fees
6 Dec - 7 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!
Family House On Highland Lake with Dock
Front of home

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Living Room

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
Pet-Friendly Farmhouse: Cozy with Large Yard
Interior

Pet-Friendly Farmhouse: Cozy with Large Yard

10.0 out of 10, Exceptional, (1)
"House has lots of room and a super nice screened in porch. Plants everywhere add a nice touch. Large fireplace, all upgraded appliances, big eat in kitchen. Property is on a busier road but backyard although clearly still a kind of cluttered farm setting Is quiet. "
Pet-Friendly Farmhouse: Cozy with Large Yard
NEW-Another Fun Downtown Location 1st floor
Exterior detail

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
Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame
Welcome to the Chateau Loches at Longmeadow,The home of vacation entertainment.

Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame

9.2 out of 10, Wonderful, (5)
"Several colleagues and I stayed here for a conference in Springfield. While the location was fairly convenient and the house was very clean, there were areas that could be improved upon. We loved having several bathrooms but there was only one roll of toilet paper in each bathroom and no extras for replacements. We ended up having to buys some. Instead of having king beds in every room, it would be nice to have one king bedroom and to have multiple beds in the other bedrooms. The basement is...
The price is AED 1,818
AED 3,959 total
includes taxes & fees
30 Nov - 1 Dec
Château at Longmeadow, Luxurious Home, 5 min from MGM & Basketball Hall of Fame
Beautiful Home - 3 King & 2 Queen - Rare Find
Living area

Beautiful Home - 3 King & 2 Queen - Rare Find

2.0 star property
The price is AED 1,033
AED 2,523 total
includes taxes & fees
9 Dec - 10 Dec
Beautiful Home - 3 King & 2 Queen - Rare Find
Pet-Friendly Westfield Home w/ Fenced Yard!
Westfield Vacation Rental | 4BR | 2BA | Steps to Enter | 1,500 Sq Ft

Pet-Friendly Westfield Home w/ Fenced Yard!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Property worked well for us "
Pet-Friendly Westfield Home w/ Fenced Yard!
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

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

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Firepit overlooking the lake.

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (47)
"What a gem this cute house was on the lake! The owners didn’t skip a beat with the attention to detail. It had everything and was so clean. Communication was spot on. We will definitely book again the next time we come to CT! We already miss waking up with coffee and watching the sun come up over the lake. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Exterior

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

9.0 out of 10, Wonderful, (2)
"Great property and a great location. The host was more than welcoming and very easy to communicate to. This was our second visit to this location and we plan to stay again if availability allows. "
The price is AED 1,091
AED 2,097 total
includes taxes & fees
2 Dec - 3 Dec
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Cozy newly remodeled home close to major amenities in Connecticut a
Living room

Cozy newly remodeled home close to major amenities in Connecticut a

8.4 out of 10, Very Good, (16)
"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
Exterior

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"Very nice and clean. Great location for proximity to our family"
Linny's Updated Lakeview Cottage - Cozy & Modern
Hilda’s Riverside Retreat
Property grounds

Hilda’s Riverside Retreat

9.8 out of 10, Exceptional, (24)
"This is a great place to stay. Clean and cozy and the hosts were great to work with. We had a breaker trip and Kelly was here within 10 min to fix it."
Hilda’s Riverside Retreat
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Pool

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (5)
"Wow"
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
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.
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Other property types in Windsor

Island Vibes Home
Living area

Island Vibes Home

10.0 out of 10, Exceptional, (8)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

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

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Exterior

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

9.0 out of 10, Wonderful, (2)
"Great property and a great location. The host was more than welcoming and very easy to communicate to. This was our second visit to this location and we plan to stay again if availability allows. "
The price is AED 1,091
AED 2,097 total
includes taxes & fees
2 Dec - 3 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.