A mountainous landscape with a lake and dense forests.

Holiday Homes in West Stockbridge

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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 West Stockbridge holiday homes

TV, fireplace, DVD player, books

1. Hudson Valley Multi-Unit Escape: Secluded + Scenic

Hudson Valley Multi-Unit Escape: Secluded + Scenic
Claverack
The price is NZ$1,769
includes taxes & fees
9 Aug - 10 Aug
Hudson Valley Multi-Unit Escape: Secluded + Scenic
Coffee/tea maker, fridge, microwave, stovetop

2. Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is NZ$1,933
includes taxes & fees
9 Aug - 10 Aug
Berkshire House Stay: 5BR/5BA
Interior

3. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is NZ$570
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Outdoor dining

4. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is NZ$1,043
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Smart TV

5. 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 NZ$763
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat
TV, fireplace, printers

6. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is NZ$2,116
includes taxes & fees
19 Aug - 20 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace, stereo

7. Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (51 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
Great Barrington, Cabin Sleeps 14, Walk To Town
Smart TV, books

8. 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 NZ$1,034
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups
3 bedrooms, iron/ironing board, WiFi, bed sheets

9. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is NZ$1,169
includes taxes & fees
1 Sept - 2 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Coffee/tea maker, fridge, microwave, oven

10. 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 NZ$410
includes taxes & fees
9 Aug - 10 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Interior

11. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is NZ$559
includes taxes & fees
26 Aug - 27 Aug
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor dining

12. 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, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is NZ$998
includes taxes & fees
6 Aug - 7 Aug
NEW RENO Historic Creamery in Berkshires w/hot tub
Exterior

13. 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 NZ$903
includes taxes & fees
1 Sept - 2 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
TV

14. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is NZ$1,046
includes taxes & fees
2 Sept - 3 Sept
Treetop Hideaway in Tyringham
Property grounds

15. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is NZ$689
includes taxes & fees
9 Aug - 10 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Coffee/tea maker, fridge, microwave, oven

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is NZ$693
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington
Outdoor dining

17. 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 NZ$2,100
includes taxes & fees
10 Aug - 11 Aug
Hancock Village Inn Near Jiminy Peak
Outdoor dining

18. 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 NZ$932
includes taxes & fees
8 Aug - 9 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

19. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is NZ$240
includes taxes & fees
9 Aug - 10 Aug
All the comforts of home
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 West Stockbridge Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"
judy 1-night trip
Posted 7 hours ago
The Red Lion Inn

Find out more about West Stockbridge

West Stockbridge Holiday Homes information

Number of reviews
173
Accommodation
496 Holiday Homes
Lowest Price
NZ$240
Highest Price
NZ$2,116