A mountainous landscape with a lake and dense forests.

West Stockbridge Holiday Rentals

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Our top choices for West Stockbridge holiday rentals

1. Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres
Stockbridge
10.0 out of 10, Exceptional, (20 reviews)
"Great home, warm and welcoming!! Hosts were great! Very attentive, enjoyed meeting Lisa. Plenty of room for our gathering, accommodations were excellent! "
United States
Amy M.
Historic Stockbridge Villa on 25 acres

2. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is NZ$525
includes taxes & fees
3 Sept - 4 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.

3. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is NZ$1,419
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape

4. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 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$675
includes taxes & fees
14 Sept - 15 Sept
stylish Berkshires Retreat

5. 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.
Spacious Central Berkshires Home for Groups

6. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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$541
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,073 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is NZ$219
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge

8. 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$2,154
includes taxes & fees
27 Aug - 28 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

9. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is NZ$3,678
includes taxes & fees
8 Sept - 9 Sept
Berkshires farm, 30+ guests, 50 acres

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$402
includes taxes & fees
19 Aug - 20 Aug
NEW RENO - Chalet-style farm loft near Tanglewood

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, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is NZ$933
includes taxes & fees
14 Sept - 15 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub

12. 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 NZ$916
includes taxes & fees
8 Sept - 9 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley

13. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is NZ$452
includes taxes & fees
13 Sept - 14 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

14. 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$1,090
includes taxes & fees
14 Sept - 15 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.

15. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveller
Renovated Downtown Great Barrington House

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is NZ$679
includes taxes & fees
25 Aug - 26 Aug
Home in Great Barrington

17. 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$680
includes taxes & fees
25 Aug - 26 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

18. 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 NZ$922
includes taxes & fees
14 Sept - 15 Sept
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

19. 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 NZ$397
includes taxes & fees
14 Sept - 15 Sept
1800s Carriage house in Berkshires / Hudson Valley

20. 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$952
includes taxes & fees
15 Sept - 16 Sept
Treetop Hideaway in Tyringham
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

Find out more about West Stockbridge

Everything you need to know about West Stockbridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the West Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect West Stockbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Stockbridge holiday rentals we have selected for you start as low as NZ$185 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Stockbridge rentals

At Expedia, we put the best West Stockbridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top West Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream West Stockbridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around West Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in West Stockbridge?

Yes, there are holiday rentals in West Stockbridge close to Hotchkiss Mobile Studio, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to West Stockbridge speak positively about the gardens and restaurants in this destination. Make sure you have time to check out the forests and lake views during your trip.

What are some of the best holiday rentals that West Stockbridge has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This highly rated holiday home rental in West Stockbridge is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in West Stockbridge?

With 21 Expedia holiday rentals, you're guaranteed to find just the right place for your West Stockbridge stay.

What can I see and do in West Stockbridge?

Family-friendly attractions include Hotchkiss Mobile Studio and Charles H. Baldwin & Sons, whereas Stockbridge Bowl is a spot to enjoy the outdoors. While here, Ebenezer II Gifts and Antiques and Hoffman's Pottery are other places worth a visit.

What are holiday rentals like in West Stockbridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in West Stockbridge. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.