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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Hancock holiday homes

A heated pool

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 AU$789
includes taxes & fees
6 Aug - 7 Aug
Comfortable Berkshires retreat on mtn resort, SISO
Pool

2. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is AU$858
includes taxes & fees
5 Aug - 6 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Outdoor dining

3. Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"good"
United States
Ismael
The price is AU$1,048
includes taxes & fees
19 Aug - 20 Aug
Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Exterior

4. White Lily Lodge 50 acre estate with private lake

White Lily Lodge 50 acre estate with private lake
Cropseyville
The price is AU$1,589
includes taxes & fees
5 Aug - 6 Aug
White Lily Lodge 50 acre estate with private lake
Outdoor dining

5. 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, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AU$783
includes taxes & fees
5 Aug - 6 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Coffee/tea maker, fridge, microwave, stovetop

6. 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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$803
includes taxes & fees
5 Aug - 6 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Outdoor dining

7. 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$1,762
includes taxes & fees
11 Aug - 12 Aug
Hancock Village Inn Near Jiminy Peak
Coffee/tea maker, fridge, microwave, oven

8. 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 AU$299
includes taxes & fees
5 Aug - 6 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Dining

9. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 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 AU$294
includes taxes & fees
9 Aug - 10 Aug
Cozy Home in Pownal VT
TV, DVD player, books, video library

10. 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$356
includes taxes & fees
5 Aug - 6 Aug
1800s Carriage house in Berkshires / Hudson Valley
Exterior

11. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 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$769
includes taxes & fees
1 Sept - 2 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Exterior

12. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Hinsdale
10.0 out of 10, Exceptional, (9 reviews)
"Kendra was an excellent host! Very nice and welcoming and answered questions promptly. The house was beautiful and the country setting and lake was picturesque. "
United States
Joseph L.
The price is AU$849
includes taxes & fees
10 Aug - 11 Aug
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Smart TV

13. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$641
includes taxes & fees
12 Aug - 13 Aug
stylish Berkshires Retreat
Exterior

14. 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 AU$657
includes taxes & fees
31 Aug - 1 Sept
North Getaway Cottage
Property grounds

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

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is AU$482
includes taxes & fees
10 Aug - 11 Aug
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Exterior

16. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is AU$642
includes taxes & fees
25 Aug - 26 Aug
The Greylock Cabin
Terrace/patio

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 AU$786
includes taxes & fees
31 Aug - 1 Sept
Treat yourself at the stunning June Farms Wellness Huts!
Smart TV, books

18. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is AU$881
includes taxes & fees
1 Sept - 2 Sept
Spacious Central Berkshires Home for Groups
Exterior detail

19. 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, (4 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$1,000
includes taxes & fees
25 Aug - 26 Aug
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Outdoor dining

20. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AU$878
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hancock Hotel Reviews

Berkshires Untold

Berkshires Untold

8/10 Good
"This is a remodeled and upgraded Motel with a new look and outfit. The rooms are recently renovated with new bathrooms, beds, and AC. Everything is clean and easily accessible, parking is in front of the door. The main building has a bar with a seating area, and there is a patio with couches and gas fire pits. One can hear the traffic from route 7, though the windows block most of the noise in the rooms. We appreciated the bar and the menu which offered a variety of drinks and food choices. The staff was very nice and accommodating, particularly, the bartender, This is a great place for a short stay over, a combination of Motel with hotel-like service to hang out with drinks and food. Highly recommended."
Kai 1-night trip
Posted 6 hours ago
Berkshires Untold

Find out more about Hancock

Hancock Holiday Homes information

Number of reviews
205
Accommodation
263 Holiday Homes
Lowest Price
AU$294
Highest Price
AU$1,762