West Stockbridge Holiday Rentals

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1 Dec - 2 Dec
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2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in West Stockbridge

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2157)
"Great views"
United States
Annalee
The price is HK$635
HK$794 total
includes taxes & fees
2 Dec - 3 Dec
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is HK$947
HK$1,058 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

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

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,135
HK$2,929 total
includes taxes & fees
2 Dec - 3 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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 HK$1,247
HK$3,071 total
includes taxes & fees
2 Dec - 3 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is HK$1,442
HK$1,611 total
includes taxes & fees
2 Dec - 3 Dec
Jiminy Peak Mountain Resort
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale
9.8 out of 10, Exceptional, (34)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Dining
Bright Boho Apt in 18th c Berkshire Farmhouse

Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough
9.0 out of 10, Wonderful, (22)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is HK$1,129
HK$1,712 total
includes taxes & fees
2 Dec - 3 Dec
Bright Boho Apt in 18th c Berkshire Farmhouse
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

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

Hancock
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is HK$817
HK$1,835 total
includes taxes & fees
3 Dec - 4 Dec
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$825
HK$1,768 total
includes taxes & fees
2 Dec - 3 Dec
Berkshires Apartment at the Stephentown Hotel
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is HK$2,328
HK$4,383 total
includes taxes & fees
2 Dec - 3 Dec
UNIQUE - 1BR Country Condo @ Jiminy Peak
TV, DVD player, books
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

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

Hancock
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is HK$817
HK$1,835 total
includes taxes & fees
2 Dec - 3 Dec
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

Hancock
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is HK$817
HK$1,835 total
includes taxes & fees
2 Dec - 3 Dec
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
The price is HK$1,268
HK$2,121 total
includes taxes & fees
2 Dec - 3 Dec
Home in Great Barrington
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

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 HK$1,051
HK$1,887 total
includes taxes & fees
4 Dec - 5 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds
All comforts of home

All comforts of home

Hudson
9.8 out of 10, Exceptional, (51)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$764
HK$1,030 total
includes taxes & fees
3 Dec - 4 Dec
All comforts of home
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

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.
The price is HK$817
HK$1,835 total
includes taxes & fees
3 Dec - 4 Dec
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
The price is HK$1,577
HK$2,318 total
includes taxes & fees
2 Dec - 3 Dec
Pet Friendly Riverfront Home in Great Barrington
Property grounds
All the comforts of home

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (28)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$827
HK$1,100 total
includes taxes & fees
2 Dec - 3 Dec
All the comforts of home
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is HK$1,207
HK$2,446 total
includes taxes & fees
2 Dec - 3 Dec
Charming 3-bedroom Cabin for nature lovers
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Hancock
9.8 out of 10, Exceptional, (18)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is HK$817
HK$1,835 total
includes taxes & fees
2 Dec - 3 Dec
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"We stayed over Thanksgiving and it did not disappoint. The customer service was great, the indoor pools were clean, there were tons of activities for kids even over the holiday. We will be back!"
Jenna 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about West Stockbridge

Search for holiday rentals in West Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in West Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in West Stockbridge
  • Use the map to find apartments and other holiday homes in the West Stockbridge neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in West Stockbridge while they last

Look no further and take a look at our great range of rental properties in West Stockbridge!

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 Hotchkiss Mobile Studio, 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.