A road lined with autumn-colored trees, a green house, and a mountain in the background.

Hancock Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Hancock vacation homes

1. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is CA $224
CA $755 total
includes taxes & fees
Sep 7 - Sep 8
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

2. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is CA $244
CA $784 total
includes taxes & fees
Sep 10 - Sep 11
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

3. 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 $871
CA $1,592 total
includes taxes & fees
Sep 30 - Oct 1
Hancock Village Inn Near Jiminy Peak
A wooden deck with a table and chairs, surrounded by a white railing.

4. 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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is CA $435
CA $765 total
includes taxes & fees
Sep 5 - Sep 6
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

5. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is CA $136
CA $332 total
includes taxes & fees
Sep 10 - Sep 11
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

6. 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 $120
CA $311 total
includes taxes & fees
Sep 14 - Sep 15
1800s Carriage house in Berkshires / Hudson Valley
A white two-story house with a porch, surrounded by trees and a hill.

7. 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 CA $350
CA $742 total
includes taxes & fees
Sep 9 - Sep 10
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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, (7 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 CA $149
CA $268 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Home in Pownal VT
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

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 $403
CA $827 total
includes taxes & fees
Sep 16 - Sep 17
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A two-story house with a front porch, a small staircase leading to the door, and a pathway flanked by bushes and a lamp post.

10. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 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 CA $312
CA $652 total
includes taxes & fees
Sep 30 - Oct 1
North Getaway Cottage
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

11. 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, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is CA $336
CA $742 total
includes taxes & fees
Sep 14 - Sep 15
NEW RENO Historic Creamery in Berkshires w/hot tub
A kitchen with white cabinets, a wooden dining table, and pendant lights.

12. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is CA $318
CA $672 total
includes taxes & fees
Sep 9 - Sep 10
A roomy remodeled retreat close to MassMoCA
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

13. The Greylock Cabin

The 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 $430
CA $694 total
includes taxes & fees
Sep 3 - Sep 4
The Greylock Cabin
A rustic wooden cabin with a chimney, surrounded by a forest.

14. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is CA $263
CA $476 total
includes taxes & fees
Sep 9 - Sep 10
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

15. 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 CA $403
CA $686 total
includes taxes & fees
Sep 24 - Sep 25
Treat yourself at the stunning June Farms Wellness Huts!
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

16. 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, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is CA $639
CA $1,189 total
includes taxes & fees
Sep 28 - Sep 29
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

17. 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 $404
CA $777 total
includes taxes & fees
Sep 15 - Sep 16
Treat yourself at the stunning June Farms Wellness Huts!
A wooden cabin with a curved roof, two windows, and a door, surrounded by a garden and forest.

18. 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 CA $404
CA $786 total
includes taxes & fees
Sep 13 - Sep 14
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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Top Hancock Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"this grand old hotel is warm and welcoming — a real hub of Bershires life and history"
James 2-night trip
Posted 5 hours ago
The Red Lion Inn

Find out more about Hancock

Hancock Vacation Homes information

Number of reviews
153
Accommodation
258 Vacation Homes
Lowest Price
CA $268
Highest Price
CA $1,592

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