Holiday Homes in Windsor
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Our top choices for Windsor holiday homes
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of MassachusettsCummington
10.0 out of 10, Exceptional, (3 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
Mary D.
The price is AU$200
includes taxes & fees
1 July - 2 July
Unique and Eclectic Small Town Suite Rental in Massachusetts
Unique and Eclectic Small Town Suite Rental in MassachusettsCummington
10.0 out of 10, Exceptional, (1 review)
"So cozy and welcoming. It was a great spot to enjoy all the beauty the Berkshire Mountains have to offer."
CJ L.
The price is AU$201
includes taxes & fees
29 June - 30 June
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is AU$686
includes taxes & fees
13 July - 14 July
Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (3 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
Jess M.
The price is AU$296
includes taxes & fees
2 July - 3 July
stylish Berkshires Retreat
stylish Berkshires RetreatLee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
Donna K.
The price is AU$682
includes taxes & fees
6 July - 7 July
5BR Berkshire Home Mins To The Mountain
5BR Berkshire Home Mins To The MountainCharlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
Jason F.
The price is AU$908
includes taxes & fees
28 June - 29 June
The Greylock Cabin
The Greylock CabinFlorida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
Anonymous traveller
The price is AU$578
includes taxes & fees
21 July - 22 July
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
Frank M.
The price is AU$631
includes taxes & fees
29 June - 30 June
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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Top Windsor Hotel Reviews
Berkshires Untold
10/10 Excellent
Find out more about Windsor
Windsor Holiday Homes information
Number of reviews | 106 |
|---|---|
Accommodation | 290 Holiday Homes |
Lowest Price | AU$200 |
Highest Price | AU$1,335 |