West Stockbridge Holiday Rentals

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Check prices for these dates

Tonight
13 Jul - 14 Jul
Tomorrow
14 Jul - 15 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in West Stockbridge

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Cozy living room with a comfortable sofa, throw blanket, and fireplace.

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

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is HK$1,994
HK$4,016 total
includes taxes & fees
6 Aug - 7 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Enjoy al fresco dining and socializing on this tranquil outdoor deck, complete with a barbecue grill and comfortable seating.

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is HK$1,389
HK$3,262 total
includes taxes & fees
28 Jul - 29 Jul
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Relax on the covered porch with two comfortable rocking chairs overlooking a serene grassy area surrounded by trees.

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is HK$2,237
HK$4,323 total
includes taxes & fees
16 Jul - 17 Jul
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is HK$4,561
HK$7,821 total
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bedroom house in charming Lee with WiFi
Berkshire Village Carriage House - Super Private!!
Enjoy cooking in this well-equipped kitchen with a central island, sink, and ample seating for two.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
The price is HK$1,570
HK$2,297 total
includes taxes & fees
31 Jul - 1 Aug
Berkshire Village Carriage House - Super Private!!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a window with a view.

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is HK$3,132
HK$5,200 total
includes taxes & fees
4 Aug - 5 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Experience Timeless Elegance in The Edith Wharton Room!
Cozy retreat with a large bed, dresser, desk, and TV.

Experience Timeless Elegance in The Edith Wharton Room!

The price is HK$1,926
HK$2,766 total
includes taxes & fees
14 Jul - 15 Jul
Experience Timeless Elegance in The Edith Wharton Room!
Cozy Carriage House room with a double bed and private balcony
Cozy retreat with a neatly made bed, bedside table, and elegant mirror.

Cozy Carriage House room with a double bed and private balcony

The price is HK$2,178
HK$3,090 total
includes taxes & fees
14 Jul - 15 Jul
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Step outside to a serene outdoor space with a deck, Adirondack chairs, and a charming playhouse.

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is HK$2,303
HK$3,248 total
includes taxes & fees
14 Jul - 15 Jul
Historic Susan B. Anthony Room - Cozy & Charming Stay
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Relax in a serene bedroom with a tufted headboard, desk, and dresser, perfect for work and rest.

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is HK$2,741
HK$3,807 total
includes taxes & fees
21 Jul - 22 Jul
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Elegant Carriage House room with a queen bed and private patio.
Cozy retreat with a large bed, dresser, and table, set amidst classic floral wallpaper and a decorative ceiling.

Elegant Carriage House room with a queen bed and private patio.

The price is HK$2,366
HK$3,327 total
includes taxes & fees
31 Jul - 1 Aug
Elegant Carriage House room with a queen bed and private patio.
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Relax in this stylish living room with a lofted area, sofa, coffee table, and floor lamp, offering a comfortable space to unwind.

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is HK$3,496
HK$4,773 total
includes taxes & fees
14 Jul - 15 Jul
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Elegant suite with a king bed, fireplace, and kitchenette.
Relax in this stylish living room with a large coffee table, two sofas, and a fireplace.

Elegant suite with a king bed, fireplace, and kitchenette.

The price is HK$3,120
HK$4,291 total
includes taxes & fees
21 Jul - 22 Jul
Elegant suite with a king bed, fireplace, and kitchenette.
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Relax in a stylish room with a comfortable bed, a small table, and a dresser, plus a large mirror and artwork on the wall.

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is HK$3,120
HK$4,291 total
includes taxes & fees
4 Aug - 5 Aug
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Cheerful 3-bedroom cottage with woodstove
Relax in a serene outdoor space surrounded by lush greenery, featuring a wicker sofa set and a coffee table.

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is HK$2,096
HK$4,218 total
includes taxes & fees
31 Jul - 1 Aug
Cheerful 3-bedroom cottage with woodstove
Home in Great Barrington
Enjoy cooking in this well-lit kitchen with a large window offering a view of the outdoors.

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is HK$2,174
HK$3,271 total
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington
Great Barrington Get Away
Enjoy cooking in this kitchen with stainless steel appliances, a large window offering a view of the outdoors, and a convenient trash can.

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is HK$3,532
HK$5,761 total
includes taxes & fees
14 Jul - 15 Jul
Great Barrington Get Away
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Relax by the large pool in our outdoor space.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (70)
"We had a wonderful stay, thank you! "
The price is HK$2,057
HK$4,314 total
includes taxes & fees
14 Jul - 15 Jul
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable Berkshires retreat on mtn resort, SISO
Relax by the pool surrounded by lush views and shaded lounge areas.

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is HK$1,523
HK$4,125 total
includes taxes & fees
20 Jul - 21 Jul
Comfortable Berkshires retreat on mtn resort, SISO
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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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?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of West Stockbridge is located in a rural location, 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 18 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.