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Our top choices for Stephentown vacation homes

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 746
AED 2,087 total
includes taxes & fees
3 Nov - 4 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 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 719 total
includes taxes & fees
3 Nov - 4 Nov
NEW RENO - Chalet-style farm loft near Tanglewood

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 312
AED 778 total
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley

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 1,886 total
includes taxes & fees
3 Nov - 4 Nov
Comfortable Berkshires retreat on mtn resort, SISO

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 617
AED 1,508 total
includes taxes & fees
3 Nov - 4 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley

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 2,117
AED 3,771 total
includes taxes & fees
3 Nov - 4 Nov
Hancock Village Inn Near Jiminy Peak

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
8.6 out of 10, Excellent, (11 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 1,654 total
includes taxes & fees
3 Nov - 4 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 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 716 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Home in Pownal VT

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
The price is AED 1,157
AED 2,393 total
includes taxes & fees
7 Nov - 8 Nov
Ellie’s Overlook, best view in the Berkshires!

10. 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)
"It was a great stay! Centrally located in the Berkshire, very comfortable beds, amazing amenities!"
United States
Molly K.
The price is AED 1,087
AED 2,068 total
includes taxes & fees
9 Nov - 10 Nov
NEW RENO Historic Creamery in Berkshires w/hot tub

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)
"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 952
AED 1,819 total
includes taxes & fees
3 Nov - 4 Nov
Treat yourself at the stunning June Farms Wellness Huts!

12. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is AED 3,324
AED 4,634 total
includes taxes & fees
4 Nov - 5 Nov
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

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 1,017
AED 2,027 total
includes taxes & fees
22 Nov - 23 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

14. 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.
The price is AED 988
AED 2,189 total
includes taxes & fees
16 Nov - 17 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

15. 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.
The price is AED 1,405
AED 2,289 total
includes taxes & fees
3 Nov - 4 Nov
Luxury Barn Near Hudson With New Private Sauna

16. Riverfront Rustic 1824 Mansion

Riverfront Rustic 1824 Mansion
Troy
8.2 out of 10, Very good, (16 reviews)
"We loved our stay in this beautiful home! The hosts were easy to communicate with and very friendly! This is a must see historic home in Troy!"
United States
Tracey S.
The price is AED 367
AED 833 total
includes taxes & fees
5 Nov - 6 Nov
Riverfront Rustic 1824 Mansion

17. 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 1,197 total
includes taxes & fees
3 Nov - 4 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

18. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Pownal
10.0 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."
United States
Claudette R.
The price is AED 1,311
AED 2,382 total
includes taxes & fees
3 Dec - 4 Dec
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

19. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 448
AED 1,080 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

20. June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often

June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often
West Sand Lake
9.8 out of 10, Exceptional, (9 reviews)
"We loved our stay here - it was beautiful, well appointed, and relaxing!"
United States
LauraS
The price is AED 1,071
AED 1,964 total
includes taxes & fees
10 Nov - 11 Nov
June Farms is like no place else on earth! "My New Happy Place" is a comment we hear quite often
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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