Hancock Vacation Rentals

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Our top choices for Hancock vacation homes

1. 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 CA $459
CA $988 total
includes taxes & fees
Nov 15 - Nov 16
Comfortable Berkshires retreat on mtn resort, SISO

2. 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 CA $897
CA $1,556 total
includes taxes & fees
Nov 17 - Nov 18
Hancock Village Inn Near Jiminy Peak

3. 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)
"Great property and the host was extremely responsive and helpful."
United States
Robbie S.
The price is CA $290
CA $817 total
includes taxes & fees
Nov 15 - Nov 16
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

4. 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 CA $100
CA $278 total
includes taxes & fees
Nov 16 - Nov 17
NEW RENO - Chalet-style farm loft near Tanglewood

5. 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 CA $121
CA $299 total
includes taxes & fees
Nov 15 - Nov 16
1800s Carriage house in Berkshires / Hudson Valley

6. 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 CA $384
CA $674 total
includes taxes & fees
Nov 15 - Nov 16
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

7. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (15 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 CA $166
CA $277 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Home in Pownal VT

8. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (6 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 CA $231
CA $582 total
includes taxes & fees
Nov 18 - Nov 19
1789 Shaker Farmhouse in Berkshires/Hudson Valley

9. 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 CA $385
CA $780 total
includes taxes & fees
Nov 29 - Nov 30
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

10. Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit
Averill Park
10.0 out of 10, Exceptional, (1 review)
""Love it! I've booked a lot of houses over the years, and this one is at the top of the list. Everything in the description and photos was spot on. The owner communicated well and responded promptly to any questions. It was the perfect fall getaway, and we look forward to coming back in the summer!""
United States
Mark R.
The price is CA $464
CA $850 total
includes taxes & fees
Nov 15 - Nov 16
Lakefront Retreat Hot Tub, Dock, Kayaks, & Firepit

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 CA $354
CA $694 total
includes taxes & fees
Nov 19 - Nov 20
Treat yourself at the stunning June Farms Wellness Huts!

12. 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 CA $449
CA $839 total
includes taxes & fees
Nov 15 - Nov 16
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

13. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is CA $436
CA $674 total
includes taxes & fees
Dec 15 - Dec 16
Greylock Cabin

14. 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 CA $353
CA $689 total
includes taxes & fees
Dec 7 - Dec 8
A roomy remodeled retreat close to MassMoCA

15. 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 CA $358
CA $826 total
includes taxes & fees
Nov 30 - Dec 1
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

16. 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 CA $409
CA $792 total
includes taxes & fees
Dec 9 - Dec 10
NEW RENO Historic Creamery in Berkshires w/hot tub

17. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is CA $487
CA $877 total
includes taxes & fees
Nov 16 - Nov 17
Secluded Family Home in Serene Stockbridge Woods

18. 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 CA $534
CA $919 total
includes taxes & fees
Nov 18 - Nov 19
Luxury Barn Near Hudson With New Private Sauna

19. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is CA $453
CA $862 total
includes taxes & fees
Nov 15 - Nov 16
Sun Filled Lenox Retreat - Minutes to Tanglewood!

20. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is CA $1,106
CA $1,803 total
includes taxes & fees
Nov 30 - Dec 1
Beautiful and Private Home Centrally Located in the Berkshires
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.

Learn more about Hancock

Ski the family-friendly slopes at Jiminy Peak Mountain Resort, where summer brings mountain biking and an alpine slide. Explore the historic Hancock Shaker Village nearby in Pittsfield to see restored buildings and learn about this unique religious community's craftsmanship.

A white building with a sign reading "Hancock Town Hall 1850" in front of a forested hillside.

Top reviews in Hancock

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