West Stockbridge Holiday Rentals

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Holiday Rentals in West Stockbridge

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2134)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is NZ$209
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (985)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
The price is NZ$284
includes taxes & fees
16 Nov - 17 Nov
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
The price is NZ$664
includes taxes & fees
16 Nov - 17 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
The price is NZ$363
includes taxes & fees
16 Nov - 17 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
The price is NZ$417
includes taxes & fees
17 Nov - 18 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is NZ$694
includes taxes & fees
16 Nov - 17 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is NZ$619
includes taxes & fees
16 Nov - 17 Nov
UNIQUE - 1BR Country Condo @ Jiminy Peak

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Our stay exceeded our expectations! The property is beautiful with a cute patio and modern furnishings/appliances. It had a homey and clean vibe and Dillon was nice enough to provide snacks, oatmeal, coffee, creamer, toothbrushes, etc. Everything we could need! We brought our two dogs and they seemed right at home and love going on walks through the fall leaves. Would definitely recommend for those with dogs, small children, or just traveling on their own!"
United States
Anja H.
The price is NZ$380
includes taxes & fees
23 Nov - 24 Nov
Berkshires Apartment at the Stephentown Hotel

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock
10.0 out of 10, Exceptional, (3)
"Great spot. Great communication. Comfortable suite."
United States
Samuel
The price is NZ$417
includes taxes & fees
17 Nov - 18 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock
10.0 out of 10, Exceptional, (8)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
United States
Kevin K.
The price is NZ$415
includes taxes & fees
17 Nov - 18 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is NZ$415
includes taxes & fees
17 Nov - 18 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is NZ$692
includes taxes & fees
3 Dec - 4 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
The price is NZ$468
includes taxes & fees
16 Nov - 17 Nov
Home in Great Barrington

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is NZ$427
includes taxes & fees
17 Nov - 18 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is NZ$256
includes taxes & fees
16 Nov - 17 Nov
Micosta Leisure Inn

The Brooks Motel: Exceptional Suite

Hillsdale
9.2 out of 10, Wonderful, (5)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
United States
Susan S.
The price is NZ$353
includes taxes & fees
16 Nov - 17 Nov
The Brooks Motel: Exceptional Suite

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (27)
"Peaceful, friendly, clean, wish I had more time to explore and hope to return one day! Thank you!!"
United States
Barbara V.
The price is NZ$249
includes taxes & fees
16 Nov - 17 Nov
All the comforts of home

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is NZ$531
includes taxes & fees
17 Nov - 18 Nov
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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$209 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 Charles H. Baldwin & Sons, 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 20 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 Charles H. Baldwin & Sons and Ebenezer II Gifts and Antiques, whereas Stockbridge Bowl is a spot to enjoy the outdoors. While here, Hotchkiss Mobile Studio 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.