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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Stephentown vacation homes

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

1. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AED 804
AED 2,259 total
includes taxes & fees
6 Nov - 7 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 764 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

3. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AED 356
AED 875 total
includes taxes & fees
9 Nov - 10 Nov
1800s Carriage house in Berkshires / Hudson Valley
Pool

4. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is AED 591
AED 1,988 total
includes taxes & fees
25 Oct - 26 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A white two-story house with a porch, surrounded by trees and a hill.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AED 665
AED 1,642 total
includes taxes & fees
18 Nov - 19 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

6. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,310
AED 4,220 total
includes taxes & fees
27 Oct - 28 Oct
Hancock Village Inn Near Jiminy Peak
A wooden deck with a table and chairs, surrounded by a white railing.

7. 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
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AED 988
AED 1,810 total
includes taxes & fees
25 Oct - 26 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is AED 426
AED 753 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Home in Pownal VT
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

9. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (8 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 1,021
AED 2,109 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

10. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is AED 1,157
AED 2,538 total
includes taxes & fees
2 Nov - 3 Nov
Ellie’s Overlook, best view in the Berkshires!
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

11. 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 952
AED 1,689 total
includes taxes & fees
28 Oct - 29 Oct
Treat yourself at the stunning June Farms Wellness Huts!
A modern building with a wooden deck and a door.

12. 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, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 1,116
AED 2,273 total
includes taxes & fees
26 Oct - 27 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A cozy living room with a sofa, a fireplace, and large windows.

14. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Near Hudson With New Private Sauna
A cozy living room with a fireplace, red and striped furniture, and large windows offering a view of greenery.

15. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
Richmond
The price is AED 3,324
AED 4,633 total
includes taxes & fees
26 Oct - 27 Oct
Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AED 735
AED 1,259 total
includes taxes & fees
25 Oct - 26 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A kitchen with a wooden countertop, white cabinets, and red chairs. There is a staircase leading to another room.

17. Riverfront Rustic 1824 Mansion

Riverfront Rustic 1824 Mansion
Troy
8.4 out of 10, Very good, (15 reviews)
"Loved the house! So much character and in a great location! "
United States
Alex V.
The price is AED 367
AED 886 total
includes taxes & fees
28 Oct - 29 Oct
Riverfront Rustic 1824 Mansion
A kitchen with white cabinets, a wooden dining table, and pendant lights.

18. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 841
AED 1,768 total
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

19. 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)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is AED 1,067
AED 2,049 total
includes taxes & fees
19 Nov - 20 Nov
Treat yourself at the stunning June Farms Wellness Huts!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Good price, affordable, a lot of amenities. A little dated but nothing was in need of repair just an update. There’s free laundry, a pool, movie night, activity list for the week you’re there. It’s a good place to stay! I will say we did lose power for 9 hours and they kept us up to date but nothing was offered for the inconvenience which was a bit disappointing as we had food in the fridge. Overall, recommend!"
Madisson 7-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

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