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Our top choices for Stephentown vacation homes

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 2,041 total
includes taxes & fees
30 Apr - 1 May
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 1,237 total
includes taxes & fees
30 Apr - 1 May
Florida Mountain Log Cabin

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 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 1,155 total
includes taxes & fees
30 Apr - 1 May
Cozy Riverside Berkshires Retreat

Riverfront Rustic 1824 Mansion

Riverfront Rustic 1824 Mansion
Troy
8.8 out of 10, Excellent, (8 reviews)
"Loved the house! So much character and in a great location! "
United States
Alex V.
The price is AED 364
AED 882 total
includes taxes & fees
4 May - 5 May
Riverfront Rustic 1824 Mansion

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
30 Apr - 1 May
Cozy Home in Pownal VT

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
30 Apr - 1 May
North Getaway Cottage

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is AED 1,012
AED 1,755 total
includes taxes & fees
30 Apr - 1 May
Treat yourself at the stunning June Farms Wellness Huts!

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.
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 1,818 total
includes taxes & fees
30 Apr - 1 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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
30 Apr - 1 May
Comfortable Berkshires retreat on mtn resort, SISO

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
4 May - 5 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is AED 601
AED 1,874 total
includes taxes & fees
26 May - 27 May
Artists’ Hideaway in Old Chatham

Downtown 3BR duplex full kitchen parking off i-787

Downtown 3BR duplex full kitchen parking off i-787
Arbor Hill
10.0 out of 10, Exceptional, (5 reviews)
"The owners gave us fresh baked bread - twice. Also helped us get parking in a location with very few spots. Real nice owners for this property and would come back any time! "
United States
Victor
The price is AED 666
AED 1,110 total
includes taxes & fees
4 May - 5 May
Downtown 3BR duplex full kitchen parking off i-787

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.
The price is AED 562
AED 1,551 total
includes taxes & fees
30 Apr - 1 May
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 816
AED 1,437 total
includes taxes & fees
26 May - 27 May
The Greylock Cabin

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AED 643
AED 1,140 total
includes taxes & fees
4 May - 5 May
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AED 380
AED 874 total
includes taxes & fees
30 Apr - 1 May
Two Brooks Lodge

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking
Pine Hills
10.0 out of 10, Exceptional, (1 review)
"The house was nicely setup and clean. The location was very central to where we needed to be. The host was very responsive. "
United States
Elizabeth P.
Spacious 4 Bedroom Home • Sleeps 8 • Private Yard • Near Hopitals • FREE Parking

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 1,745
AED 3,163 total
includes taxes & fees
5 May - 6 May
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
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 Stephentown Hotel Reviews