West Stockbridge Holiday Rentals

  • 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
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for West Stockbridge holiday rentals

Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,128
HK$5,320 total
includes taxes & fees
12 Mar - 13 Mar
Guesthouse Cabin vacation rentals in Berkshire County
Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is HK$1,533
HK$4,329 total
includes taxes & fees
13 Mar - 14 Mar
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,295 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is HK$813
HK$994 total
includes taxes & fees
12 Mar - 13 Mar
Vacation Village in the Berkshires
Exterior

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (139 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is HK$1,016
HK$1,138 total
includes taxes & fees
28 Mar - 29 Mar
Micosta Leisure Inn
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,972
HK$4,186 total
includes taxes & fees
1 Apr - 2 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
TV, fireplace, printers

Holiday Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (4 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 HK$4,429
HK$10,392 total
includes taxes & fees
12 Mar - 13 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

Holiday Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$1,754
HK$4,319 total
includes taxes & fees
15 Mar - 16 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor dining

Holiday Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
7.8 out of 10, Good, (7 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 HK$2,104
HK$3,871 total
includes taxes & fees
24 Mar - 25 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Smart TV, books

Holiday Home in Sherwood Forest

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,253
HK$3,085 total
includes taxes & fees
23 Mar - 24 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Outdoor pool, a heated pool

Holiday Home in Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
9.8 out of 10, Exceptional, (30 reviews)
"The home was as described. Exceptional. It was immaculate and well stocked."
United States
judy h.
The price is HK$4,772
HK$8,576 total
includes taxes & fees
12 Mar - 13 Mar
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Exterior detail

Holiday Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is HK$1,513
HK$2,485 total
includes taxes & fees
23 Mar - 24 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
Daily to-go breakfast for a fee

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,154
HK$1,290 total
includes taxes & fees
10 Apr - 11 Apr
Jiminy Peak Mountain Resort
Interior

Holiday Home in Becket

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, attentive host. Location is as peaceful as can be. "
United States
Rick M.
The price is HK$2,761
HK$5,023 total
includes taxes & fees
24 Mar - 25 Mar
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Interior

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,584
HK$2,478 total
includes taxes & fees
12 Mar - 13 Mar
Family Ski Getaway in the Berkshires
Property grounds

Apartment in Hudson

All comforts of home
9.6 out of 10, Exceptional, (54 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$767
HK$1,034 total
includes taxes & fees
18 Mar - 19 Mar
All comforts of home
TV

Holiday Home in Monterey

Treetop Hideaway in Tyringham
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,065
HK$4,364 total
includes taxes & fees
24 Mar - 25 Mar
Treetop Hideaway in Tyringham
Property grounds

Holiday Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,853
HK$3,948 total
includes taxes & fees
24 Mar - 25 Mar
Cheerful 3-bedroom cottage with woodstove
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,173
HK$1,489 total
includes taxes & fees
12 Mar - 13 Mar
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,296
HK$2,155 total
includes taxes & fees
15 Mar - 16 Mar
Home in Great Barrington
Fridge, microwave, oven, stovetop

Holiday Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$2,641
HK$5,370 total
includes taxes & fees
18 Mar - 19 Mar
Spacious 5-bedroom house in charming Lee with WiFi
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 West Stockbridge Hotel Reviews

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Clean, good service "
Heather 1-night trip
Posted 2 hours ago
Courtyard by Marriott Lenox Berkshires

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 5 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 19 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.