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Our top choices for Windsor vacation homes

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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 AED 731
AED 1,872 total
includes taxes & fees
22 Apr - 23 Apr
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

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, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is AED 588
AED 1,449 total
includes taxes & fees
4 May - 5 May
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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 AED 536
AED 1,382 total
includes taxes & fees
4 May - 5 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AED 675
AED 1,253 total
includes taxes & fees
4 May - 5 May
Florida Mountain Log Cabin

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (48 reviews)
"Our crew stayed here while working on a job in the area, they absolutely loved it, cleanliness was outstanding! Host provided great information about the area which was very helpful. Amenities are great! Would recommend 100% "
United States
Maureen A.
The price is AED 1,010
AED 2,322 total
includes taxes & fees
22 Apr - 23 Apr
Spacious 5BR w/ Hot Tub & Games

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 775 total
includes taxes & fees
26 Apr - 27 Apr
Private bed with En-suite bathroom Marigold Room

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 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 AED 744
AED 1,647 total
includes taxes & fees
22 Apr - 23 Apr
North Getaway Cottage

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 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 AED 426
AED 749 total
includes taxes & fees
22 Apr - 23 Apr
Cozy Home in Pownal VT

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is AED 628
AED 1,514 total
includes taxes & fees
26 Apr - 27 Apr
Near Tanglewood: Historic Summer Retreat

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 294
AED 411 total
includes taxes & fees
19 May - 20 May
Real Estate: Therapy - Lake, Laundry, Love it

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AED 628
AED 1,526 total
includes taxes & fees
27 Apr - 28 Apr
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 AED 988
AED 1,814 total
includes taxes & fees
23 Apr - 24 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AED 1,319
AED 2,667 total
includes taxes & fees
22 Apr - 23 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 1,997 total
includes taxes & fees
25 Apr - 26 Apr
Comfortable Berkshires retreat on mtn resort, SISO

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is AED 868
AED 1,495 total
includes taxes & fees
4 May - 5 May
The Greylock Cabin

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (3 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AED 765
AED 1,720 total
includes taxes & fees
2 May - 3 May
Riverbend Berkshire East Basecamp - 3 bedrooms available

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
Spacious 5-bedroom house in charming Lee with WiFi

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.8 out of 10, Exceptional, (7 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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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