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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

Our top choices for Spencertown vacation homes

Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is AED 390
AED 519 total
includes taxes & fees
11 Jun - 12 Jun
All the comforts of home
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 1,163 total
includes taxes & fees
9 Jun - 10 Jun
Cozy Riverside Berkshires Retreat
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is AED 585
AED 1,396 total
includes taxes & fees
15 Jun - 16 Jun
stylish Berkshires Retreat
Outdoor dining

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is AED 783
AED 1,268 total
includes taxes & fees
9 Jun - 10 Jun
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Exterior

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 532
AED 1,402 total
includes taxes & fees
9 Jun - 10 Jun
Near Tanglewood: Historic Summer Retreat
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AED 735
AED 1,242 total
includes taxes & fees
9 Jun - 10 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AED 1,058
AED 2,151 total
includes taxes & fees
9 Jun - 10 Jun
Treetop Hideaway in Tyringham
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
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AED 643
AED 2,053 total
includes taxes & fees
9 Jun - 10 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is AED 876
AED 1,340 total
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington
Exterior detail

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is AED 896
AED 2,053 total
includes taxes & fees
11 Jun - 12 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Pool

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (6 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is AED 826
AED 1,921 total
includes taxes & fees
9 Jun - 10 Jun
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Interior

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is AED 646
AED 1,986 total
includes taxes & fees
22 Jun - 23 Jun
Charles Cottage Near Warren St New Renovation
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 871
AED 1,855 total
includes taxes & fees
9 Jun - 10 Jun
Cheerful 3-bedroom cottage with woodstove
Interior

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 588
AED 1,474 total
includes taxes & fees
9 Jun - 10 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Private kitchen

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.
The price is AED 645
AED 1,553 total
includes taxes & fees
10 Jun - 11 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
Property grounds

Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit
Athens
The price is AED 865
AED 1,875 total
includes taxes & fees
9 Jun - 10 Jun
Larkspire I Sleepy Hollow Lake I Beach & Firepit
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 AED 1,154
AED 2,027 total
includes taxes & fees
9 Jun - 10 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is AED 1,293
AED 2,596 total
includes taxes & fees
15 Jun - 16 Jun
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,102
AED 1,957 total
includes taxes & fees
9 Jun - 10 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop

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.
The price is AED 1,736
AED 3,153 total
includes taxes & fees
14 Jun - 15 Jun
Spacious 5-bedroom house in charming Lee with WiFi
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 Spencertown Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Very spacious and a good spot if you like to cook for yourself. Decor is dated but it's clean and good value."
Barbara 1-night trip
Posted 9 hours ago
Berkshire Mountain Lodge