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

Holiday Homes in Hancock

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Hancock holiday 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 AU$718
includes taxes & fees
4 Nov - 5 Nov
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 AU$1,450
includes taxes & fees
4 Nov - 5 Nov
Hancock Village Inn Near Jiminy Peak

3. 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 AU$280
includes taxes & fees
16 Nov - 17 Nov
NEW RENO - Chalet-style farm loft near Tanglewood

4. 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 AU$795
includes taxes & fees
16 Nov - 17 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 AU$305
includes taxes & fees
16 Nov - 17 Nov
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 AU$658
includes taxes & fees
4 Nov - 5 Nov
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, (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 AU$279
includes taxes & fees
8 Nov - 9 Nov
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, (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 AU$583
includes taxes & fees
4 Nov - 5 Nov
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 AU$761
includes taxes & fees
22 Nov - 23 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

10. 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 AU$815
includes taxes & fees
16 Nov - 17 Nov
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

11. 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 AU$932
includes taxes & fees
7 Nov - 8 Nov
Ellie’s Overlook, best view in the Berkshires!

12. 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 AU$751
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

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 AU$665
includes taxes & fees
1 Dec - 2 Dec
Greylock Cabin

14. 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 AU$810
includes taxes & fees
9 Nov - 10 Nov
NEW RENO Historic Creamery in Berkshires w/hot tub

15. 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 AU$679
includes taxes & fees
9 Nov - 10 Nov
A roomy remodeled retreat close to MassMoCA

16. 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 AU$825
includes taxes & fees
17 Nov - 18 Nov
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

17. 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 AU$1,778
includes taxes & fees
4 Nov - 5 Nov
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

18. 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 AU$877
includes taxes & fees
9 Nov - 10 Nov
Secluded Family Home in Serene Stockbridge Woods

19. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is AU$1,777
includes taxes & fees
10 Nov - 11 Nov
Beautiful and Private Home Centrally Located in the Berkshires

20. 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 AU$933
includes taxes & fees
4 Nov - 5 Nov
Luxury Barn Near Hudson With New Private Sauna
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hancock Hotel Reviews

Find out more about Hancock

Hancock Holiday Homes information

Number of reviews
236
Accommodation
269 Holiday Homes
Lowest Price
AU$279
Highest Price
AU$1,778