130+ Vacation Rentals Near Chesterwood |
  1. USA
  2. Massachusetts
  3. West Stockbridge
  4. Chesterwood

Sell Off Cruises - Vacation Rentals in Chesterwood

Tranquil 3 BR Stockbridge House w/Private Deck! in Stockbridge From US $412
         

10.0 (97 Reviews)
House
Tranquil 3 BR Stockbridge House w/Private Deck!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Too Good AKA 2 Goodrich St in Stockbridge From US $600
         

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10.0 (2 Reviews)
House
Too Good AKA 2 Goodrich St
  • Air Conditioner
  • View
  • Security/Safety

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The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood in Stockbridge From US $399
         

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9.2 (114 Reviews)
Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
  • Air Conditioner
  • Parking
  • Pool

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Completely Renovated Historic Home in the Heart of the Berkshires in Glendale From US $467
         

10.0 (15 Reviews)
House
Completely Renovated Historic Home in the Heart of the Berkshires
  • Air Conditioner
  • Parking
  • TV

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Beautiful House in the Woods, Huge Yard, Hot Tub in Great Barrington From US $360
         

10.0 (1 Review)
House
Beautiful House in the Woods, Huge Yard, Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Red Lion Inn in Stockbridge From US $233
         

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8.8 (1016 Reviews)
Hotel
The Red Lion Inn
  • Air Conditioner
  • Parking
  • Pool

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Stockbridge Village in Summer in Stockbridge From US $317
         

9.2 (22 Reviews)
House
Stockbridge Village in Summer
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tranquil 3 BR Stockbridge House w/Private Deck! in Stockbridge From US $379
         

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9.5 (2 Reviews)
House
Tranquil 3 BR Stockbridge House w/Private Deck!
  • Parking
  • Pet Friendly
  • Security/Safety

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Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires! in Stockbridge From US $368
         

10.0 (70 Reviews)
House
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
  • Air Conditioner
  • Parking
  • TV

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Walk into town, soak up sun on enclosed porch & steps away from nature trails! in Stockbridge From US $856
         

10.0 (39 Reviews)
House
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
  • Air Conditioner
  • Parking
  • TV

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Classic Stockbridge Cottage in Stockbridge From US $574
         

10.0 (19 Reviews)
House
Classic Stockbridge Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stockbridge pied-à-terre in Stockbridge From US $338
         

10.0 (15 Reviews)
House
Stockbridge pied-à-terre
  • Air Conditioner
  • Parking
  • TV

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Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests in Stockbridge From US $845
         

10.0 (12 Reviews)
House
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
  • Air Conditioner
  • Parking
  • TV

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Beautiful House in the Woods: Huge Yard, Hot Tub in Great Barrington From US $722
         

10.0 (10 Reviews)
House
Beautiful House in the Woods: Huge Yard, Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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8 Mi to Tanglewood & Butternut Ski: Spacious Home! in Housatonic From US $659
         

10.0 (7 Reviews)
House
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Serene and Refined Berkshires Retreat, Close to Kripalu, Gardens & 3 Ski Resorts in Stockbridge From US $840
         

10.0 (6 Reviews)
House
Serene and Refined Berkshires Retreat, Close to Kripalu, Gardens & 3 Ski Resorts
  • Air Conditioner
  • Parking
  • TV

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Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge in Stockbridge From US $617
         

10.0 (5 Reviews)
Apartment
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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1 Mi to Dtwn: Cottage w/Large Yard in Stockbridge in Stockbridge From US $382
         

10.0 (4 Reviews)
Cottage
1 Mi to Dtwn: Cottage w/Large Yard in Stockbridge
  • Air Conditioner
  • Parking
  • TV

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Lakeshore cabin with beach and dock in Stockbridge From US $371
         

10.0 (4 Reviews)
Cabin
Lakeshore cabin with beach and dock
  • Parking
  • TV
  • Security/Safety

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Sunset River Views, SIP, Spotless, Sleeps 8 in Housatonic From US $603
         

10.0 (3 Reviews)
House
Sunset River Views, SIP, Spotless, Sleeps 8
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pixley Forest | 15 Mins To Tanglewood Fireplace in West Stockbridge From US $389
         

10.0 (1 Review)
House
Pixley Forest | 15 Mins To Tanglewood Fireplace
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hearth House | Prime Location! in Stockbridge From US $331
         

10.0 (1 Review)
House
Hearth House | Prime Location!
  • Air Conditioner
  • Parking
  • TV

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A Grand property in Historic Stockbridge in Stockbridge From US $1,576
         

9.8 (107 Reviews)
House
A Grand property in Historic Stockbridge
  • Air Conditioner
  • Parking
  • TV

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Stockbridge Village Cottage With Mountain View’s and walk to town in Stockbridge From US $602
         

9.8 (66 Reviews)
House
Stockbridge Village Cottage With Mountain View’s and walk to town
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Selloffcruises makes it easy to compare the best listings on Selloffcruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selloffcruises homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chesterwood.

Weather in Chesterwood

View the weather forecast for Chesterwood before booking your Chesterwood Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chesterwood, MA

Selloffcruises offers a large selection of top attractions around Chesterwood. Research things to do on your vacation before you visit Chesterwood.


Tanglewood Music Center Ski Butternut Catamount Ski Area Norman Rockwell Museum National Shrine of the Divine Mercy Lee Prime Outlets Bousquet Ski Area Cranwell Golf Club Jacob's Pillow Berkshire Museum Hancock Shaker Village Pittsfield State Forest October Mountain State Forest Beartown State Forest The Mount Shakespeare and Company Taconic State Park Kennedy Park Naumkeag Colonial Theater

Chesterwood Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Chesterwood?

Currently, the total number of properties listed in 2026 is over 130 in the Chesterwood area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesterwood.