Short-Term Rentals in Chesterwood, MA: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Short-Term Rentals
  3.  USA

  4.  Massachusetts

  5.  West Stockbridge
  6.  Chesterwood

Refine your search

Price per night

Amenity Filter

Rating

235 Best Short-Term Rentals in Chesterwood (Starting from $203)

Classic Stockbridge Cottage
Classic Stockbridge Cottage
House
Stockbridge, MA, USA
0.4k from Chesterwood center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
Check Availability
Peaceful Woodland Home in the Heart of the Berkshires
Peaceful Woodland Home in the Heart of the Berkshires
House
Glendale, MA, 01229, United States
0.2k from Chesterwood center

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

3 Bedrooms8 Guests
9.8

Exceptional

52 reviews

$355
Average price / night
Check Availability
Tranquil 3 BR Stockbridge House with Private Deck!
Tranquil 3 BR Stockbridge House with Private Deck!
House
Stockbridge, MA, USA
1.4k from Chesterwood 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
Check Availability
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
0.3k from Chesterwood center

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

2 Bedrooms4 Guests
10.0

Exceptional

14 reviews

$357
Average price / night
Check Availability
1 Mi to Dtwn Cottage with Large Yard in Stockbridge
1 Mi to Dtwn Cottage with Large Yard in Stockbridge
House
Stockbridge, MA, USA
2.5k from Chesterwood center

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

4 Bedrooms8 Guests
New to Booking
$354
Average price / night
Check Availability
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
2.6k from Chesterwood center

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

6 Bedrooms14 Guests
New to Booking
$474
Average price / night
Check Availability
Modern Cottage in the heart of the Berkshires with new exterior flex space!
Modern Cottage in the heart of the Berkshires with new exterior flex space!
House
Stockbridge, MA, 01262, United States
1.3k from Chesterwood center

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

3 Bedrooms8 Guests
10.0

Exceptional

97 reviews

$521
Average price / night
Check Availability
8 Mi to Tanglewood and Butternut Ski Spacious Home!
8 Mi to Tanglewood and Butternut Ski Spacious Home!
House
Housatonic, MA, USA
2.6k from Chesterwood 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
Check Availability
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
1.4k from Chesterwood center

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

4 Bedrooms8 Guests
New to Booking
$398
Average price / night
Check Availability
Stockbridge Retreat with Pool and Hot Tub!
Stockbridge Retreat with Pool and Hot Tub!
House
Stockbridge, MA, USA
2.7k from Chesterwood center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms10 Guests
New to Booking
$1413
Average price / night
Check Availability
Tranquil 3 BR Stockbridge House w/ Private Deck!
Tranquil 3 BR Stockbridge House w/ Private Deck!
House
Stockbridge, MA, 01262, United States
1.4k from Chesterwood center

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

3 Bedrooms6 Guests
10.0

Exceptional

95 reviews

$307
Average price / night
Check Availability
Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires
Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires
House
Stockbridge, MA, USA
2.7k from Chesterwood center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$351
Average price / night
Check Availability
Pixley Forest | 15 Mins To Tanglewood • Fireplace
Pixley Forest | 15 Mins To Tanglewood • Fireplace
House
West Stockbridge, MA, 01236, United States
1.8k from Chesterwood center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$512
Average price / night
Check Availability
Woodland Zen by AvantStay Modern Design Patio
Woodland Zen by AvantStay Modern Design Patio
House
Stockbridge, MA, USA
2.7k from Chesterwood center

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

1 Bedroom6 Guests
New to Booking
$1342
Average price / night
Check Availability
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
1.8k from Chesterwood center

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

4 Bedrooms9 Guests
New to Booking
$852
Average price / night
Check Availability
Steps to Downtown Stockbridge Home with Patio!
Steps to Downtown Stockbridge Home with Patio!
House
Stockbridge, MA, USA
2.8k from Chesterwood center

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

2 Bedrooms5 Guests
New to Booking
$260
Average price / night
Check Availability
Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge Woods
House
Stockbridge, MA, 01262, United States
1.8k from Chesterwood center

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

3 Bedrooms8 Guests
10.0

Exceptional

23 reviews

$454
Average price / night
Check Availability
2 Mi to Norman Rockwell Museum Stockbridge Apt!
2 Mi to Norman Rockwell Museum Stockbridge Apt!
Apartment
Stockbridge, MA, USA
2.9k from Chesterwood center

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

1 Bedroom2 Guests
New to Booking
$203
Average price / night
Check Availability
Special Spring Rate!\nClassic Berkshire Retreat
Special Spring Rate!\nClassic Berkshire Retreat
House
Stockbridge, MA, 01262, United States
2.0k from Chesterwood center

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

3 Bedrooms10 Guests
9.6

Exceptional

10 reviews

$360
Average price / night
Check Availability
Too Good AKA 2 Goodrich St
Too Good AKA 2 Goodrich St
House
Stockbridge, MA, USA
2.9k from Chesterwood center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

8 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$499
Average price / night
Check Availability
A Charming Mid 1800's Stockbridge Farmhouse.
A Charming Mid 1800's Stockbridge Farmhouse.
House
Stockbridge, MA, 01263, United States
2.0k from Chesterwood center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms6 Guests
10.0

Exceptional

34 reviews

$359
Average price / night
Check Availability
Beautiful House in the Woods, Huge Yard, Hot Tub
Beautiful House in the Woods, Huge Yard, Hot Tub
House
Great Barrington, MA, USA
4.4k from Chesterwood center

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

1 Bedroom8 Guests
New to Booking
$360
Average price / night
Check Availability
Serene and Refined Berkshires Retreat, Close to Kripalu, Gardens & 3 Ski Resorts
Serene and Refined Berkshires Retreat, Close to Kripalu, Gardens & 3 Ski Resorts
House
Stockbridge, MA, 01262, United States
2.3k from Chesterwood center

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

4 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$630
Average price / night
Check Availability
Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay
Forest Views, Enclosed Patio in Secluded Modern Home | Woodland Zen by AvantStay
House
Stockbridge, MA, 01262, United States
2.3k from Chesterwood center

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

3 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$311
Average price / night
Check Availability
Fabulous Tanglewood Getaway!
Fabulous Tanglewood Getaway!
Cottage
Stockbridge, MA, 01262, United States
2.3k from Chesterwood center

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

1 Bedroom4 Guests
10.0

Exceptional

14 reviews

$259
Average price / night
Check Availability
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Cottage
Stockbridge, MA, 01262, United States
2.5k from Chesterwood center

AC, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space, Patio

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$442
Average price / night
Check Availability
Beautifully Restored 1860's Stockbridge Farmhouse- short walk to downtown!
Beautifully Restored 1860's Stockbridge Farmhouse- short walk to downtown!
House
Stockbridge, MA, 01262, United States
2.5k from Chesterwood center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$479
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 Short-Term Rentals in Chesterwood.

Chesterwood Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 235 verified short-term rentals in Chesterwood, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Chesterwood vary depending on location, property size, and travel dates. Rates typically start from around $203 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Chesterwood include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Chesterwood, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Chesterwood often include amenities such as Fireplace/Heating, Internet, and Pet Friendly, providing a comfortable and convenient stay.

Short-term rentals in Chesterwood are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.