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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 SAR 394
SAR 637 total
includes taxes & fees
24 Nov - 25 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, (2)
"Beautiful & well-maintained historic home.... everything was perfect! Amendies were first class! We will be back:)"
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 SAR 282
SAR 639 total
includes taxes & fees
16 Nov - 17 Nov
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 SAR 702
SAR 1,379 total
includes taxes & fees
21 Nov - 22 Nov
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 SAR 939
SAR 1,504 total
includes taxes & fees
18 Nov - 19 Nov
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)
"This was a fantastic home, property and location. Great places to eat close by. Property was fully fenced with plenty of space for kids and pets. 1 slight issue which was quickly rectified even at 11PM in the evening. Great communication!!"
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 SAR 1,859
SAR 4,048 total
includes taxes & fees
16 Nov - 17 Nov
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 SAR 938
SAR 2,399 total
includes taxes & fees
19 Nov - 20 Nov
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
10.0 out of 10, Exceptional, (1)
"Pictures are accurate . The place was more than I expected."
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 SAR 1,078
SAR 2,094 total
includes taxes & fees
17 Nov - 18 Nov
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
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
Our open concept living room makes the small home feel spacious and comfortable
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
9.8 out of 10, Exceptional, (54)
"Enjoyed our stay. "
Lakeview Cottage, 5 minute walk to the beach. Southwick, MA
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

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 SAR 1,078
SAR 2,094 total
includes taxes & fees
17 Nov - 18 Nov
A “Wow” Experience everywhere there is something to stimulate your mind Interest
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!
Bungalow House - Free Parking - 10 mins to Hartford & Airport
Living area
Bungalow House - Free Parking - 10 mins to Hartford & Airport
8.0 out of 10, Very Good, (22)
"House was very clean. Everything was as described and the Owner was very responsive to our requests pre checkin."
Bungalow House - Free Parking - 10 mins to Hartford & 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.