Vacation Rentals in West Stockbridge, MA: Compare 10+ Sites & Save

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208 Best Vacation Rentals in West Stockbridge (Starting from $203)

Tranquil 3 BR Stockbridge House with Private Deck!
Tranquil 3 BR Stockbridge House with Private Deck!
House
Stockbridge, MA, USA
3.2k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$265
Average price / night
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Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests
Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests
House
West Stockbridge, MA, 01266, United States
1.1k from West Stockbridge center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
8.6

Fabulous

12 reviews

$541
Average price / night
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Classic Stockbridge Cottage
Classic Stockbridge Cottage
House
Stockbridge, MA, USA
4.1k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
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Cozy Home on 17 acres in W Stockbridge. Close to the Pike, Slopes, Tanglewood
Cozy Home on 17 acres in W Stockbridge. Close to the Pike, Slopes, Tanglewood
House
West Stockbridge, MA, 01236, United States
1.3k from West Stockbridge center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms10 Guests
New to Booking
$330
Average price / night
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Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods
Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods
House
West Stockbridge, MA, USA
4.9k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

6 Bedrooms14 Guests
New to Booking
$474
Average price / night
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Crossbridge: Vintage Charm + Unique Character.
Crossbridge: Vintage Charm + Unique Character.
House
West Stockbridge, MA, 01266, United States
1.9k from West Stockbridge center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms11 Guests
New to Booking
$1023
Average price / night
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8 Mi to Tanglewood and Butternut Ski Spacious Home!
8 Mi to Tanglewood and Butternut Ski Spacious Home!
House
Housatonic, MA, USA
4.9k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

6 Bedrooms14 Guests
8.0

Good

1 reviews

$406
Average price / night
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6 Mi to Tanglewood Peaceful Berkshire Apt!
6 Mi to Tanglewood Peaceful Berkshire Apt!
Apartment
Richmond, MA, USA
5.0k from West Stockbridge center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$300
Average price / night
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Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home
Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home
House
West Stockbridge, MA, 01266, United States
2.6k from West Stockbridge center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms9 Guests
New to Booking
$852
Average price / night
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Wellspring by AvantStay Indoor Pool Views
Wellspring by AvantStay Indoor Pool Views
House
Richmond, MA, USA
5.2k from West Stockbridge center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$960
Average price / night
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Pixley Forest | 15 Mins To Tanglewood • Fireplace
Pixley Forest | 15 Mins To Tanglewood • Fireplace
House
West Stockbridge, MA, 01236, United States
2.8k from West Stockbridge center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$512
Average price / night
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Woodland Zen by AvantStay Modern Design Patio
Woodland Zen by AvantStay Modern Design Patio
House
Stockbridge, MA, USA
5.4k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$1342
Average price / night
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Sunny West Stockbridge, Main floor Primary!
Sunny West Stockbridge, Main floor Primary!
House
West Stockbridge, MA, 01266, United States
3.0k from West Stockbridge center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, No Smoking, TV, Washer

3 Bedrooms6 Guests
New to Booking
$621
Average price / night
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Cozy Stockbridge Cabin - Walk to Beach and Lake!
Cozy Stockbridge Cabin - Walk to Beach and Lake!
House
Stockbridge, MA, USA
5.6k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$224
Average price / night
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
House
West Stockbridge, MA, 01266, United States
3.1k from West Stockbridge center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

76 reviews

$398
Average price / night
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Steps to Downtown Stockbridge Home with Patio!
Steps to Downtown Stockbridge Home with Patio!
House
Stockbridge, MA, USA
6.1k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms5 Guests
New to Booking
$260
Average price / night
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Tranquil 3 BR Stockbridge House w/ Private Deck!
Tranquil 3 BR Stockbridge House w/ Private Deck!
House
Stockbridge, MA, 01262, United States
3.2k from West Stockbridge center

AC, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

95 reviews

$307
Average price / night
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2 Mi to Norman Rockwell Museum Stockbridge Apt!
2 Mi to Norman Rockwell Museum Stockbridge Apt!
Apartment
Stockbridge, MA, USA
6.1k from West Stockbridge center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$203
Average price / night
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Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge Woods
House
Stockbridge, MA, 01262, United States
3.4k from West Stockbridge center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$454
Average price / night
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Beautiful House in the Woods, Huge Yard, Hot Tub
Beautiful House in the Woods, Huge Yard, Hot Tub
House
Great Barrington, MA, USA
6.1k from West Stockbridge center

Security/Safety, Balcony/Terrace, Barbecue/Outdoor Cooking, Air Conditioner, Pet Friendly, Parking, View

1 Bedroom8 Guests
New to Booking
$360
Average price / night
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Completely Renovated Historic Home in the Heart of the Berkshires
Completely Renovated Historic Home in the Heart of the Berkshires
House
Glendale, MA, 01229, United States
3.6k from West Stockbridge center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

14 reviews

$357
Average price / night
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1 Mi to Dtwn Cottage with Large Yard in Stockbridge
1 Mi to Dtwn Cottage with Large Yard in Stockbridge
House
Stockbridge, MA, USA
6.2k from West Stockbridge center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$354
Average price / night
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Peaceful Woodland Home in the Heart of the Berkshires
Peaceful Woodland Home in the Heart of the Berkshires
House
Glendale, MA, 01229, United States
3.7k from West Stockbridge center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms8 Guests
9.8

Exceptional

52 reviews

$355
Average price / night
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Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
House
West Stockbridge, MA, 01266, United States
4.0k from West Stockbridge center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$545
Average price / night
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Stockbridge house 17 minutes from Tanglewood.  Four bedroom, three bathroom.
Stockbridge house 17 minutes from Tanglewood. Four bedroom, three bathroom.
House
Stockbridge, MA, 01229, United States
4.1k from West Stockbridge center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$398
Average price / night
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Elegant & private light-filled privacy
Elegant & private light-filled privacy
House
stockbridge, MA, 01262, United States
4.1k from West Stockbridge center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms5 Guests
2.0

Review score

1 reviews

$667
Average price / night
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Shaker Pine Cabin: your cozy Berkshires retreat in the middle of it all!
Shaker Pine Cabin: your cozy Berkshires retreat in the middle of it all!
Cabin
West Stockbridge, MA, 01266, United States
4.2k from West Stockbridge center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

4 Bedrooms9 Guests
New to Booking
$708
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in West Stockbridge.

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Frequently Asked Questions

You can explore 208 verified vacation rentals in West Stockbridge. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in West Stockbridge vary depending on the season, property size, and location. Rates typically start from around $203 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in West Stockbridge include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in West Stockbridge welcome pets. Currently, 39 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in West Stockbridge often include amenities such as Fireplace/Heating, Internet, and Pet Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.