Default HTG hotel image

Holiday Homes in Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Windsor holiday homes

Property grounds

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 Massachusetts
Cummington
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."
United States
Mary D.
The price is €124
includes taxes & fees
29 Jun - 30 Jun
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Property grounds

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
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."
United States
CJ L.
The price is €124
includes taxes & fees
2 Jul - 3 Jul
Unique and Eclectic Small Town Suite Rental in Massachusetts
Interior

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."
United States
Sharon K.
The price is €429
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
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."
United States
Jess M.
The price is €183
includes taxes & fees
29 Jun - 30 Jun
Cozy Home in Pownal VT
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
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."
United States
Donna K.
The price is €421
includes taxes & fees
6 Jul - 7 Jul
stylish Berkshires Retreat
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
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! "
United States
Jason F.
The price is €546
includes taxes & fees
28 Jun - 29 Jun
5BR Berkshire Home Mins To The Mountain
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is €360
includes taxes & fees
21 Jul - 22 Jul
The Greylock Cabin
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €382
includes taxes & fees
29 Jun - 30 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is €124
includes taxes & fees
26 Jun - 27 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is €486
includes taxes & fees
28 Jun - 29 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (25 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is €388
includes taxes & fees
29 Jun - 30 Jun
North Getaway Cottage
Exterior

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is €485
includes taxes & fees
8 Jul - 9 Jul
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (50 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
Spacious 5BR w/ Hot Tub & Games
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is €827
includes taxes & fees
8 Jul - 9 Jul
Riverbend Berkshire East Basecamp - 3 bedrooms available
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is €646
includes taxes & fees
2 Jul - 3 Jul
Comfortable Berkshires retreat on mtn resort, SISO
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is €477
includes taxes & fees
29 Jun - 30 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

Historic, Waterfront Suite Rental close to Boston, Massachusetts

Historic, Waterfront Suite Rental close to Boston, Massachusetts
Cummington
The price is €124
includes taxes & fees
26 Jun - 27 Jun
Historic, Waterfront Suite Rental close to Boston, Massachusetts
Property grounds

Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts

Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts
Cummington
The price is €124
includes taxes & fees
29 Jun - 30 Jun
Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"I usually stay here and yes staff are nice and rooms are decent but I’ve seen a decline in amenities. Maybe the expense of things - bathrobe in room, water and snacks were what I was used to seeing .in the room."
Kimberly 1-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
15,024
Accommodation
274 Holiday Homes
Lowest Price
€61
Highest Price
€201