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

Visittheus - Vacation Rentals in Chesterwood

Property Image From $356
         

10.0 (90 Reviews)
House
Tranquil 3 BR Stockbridge House w/Private Deck!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $351
         

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10.0 (2 Reviews)
House
Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $322
         

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10.0 (93 Reviews)
House
148 m² House ∙ 3 bedrooms ∙ 6 guests
  • 1593 ft² House
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $374
         

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9.2 (105 Reviews)
Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $357
         

10.0 (13 Reviews)
House
Completely Renovated Historic Home in the Heart of the Berkshires
  • Air Conditioner
  • Parking
  • TV

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Property Image From $499
         

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10.0 (1 Review)
House
Too Good AKA 2 Goodrich St
  • Air Conditioner
  • View
  • Security/Safety

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Property Image From $1,227
         

10.0 (3 Reviews)
House
362 m² House ∙ 4 bedrooms ∙ 10 guests
  • 3896 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $269
         

6.4 (22 Reviews)
Bed & Breakfast
Tanglewood Suites
  • Air Conditioner
  • Parking
  • TV

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Property Image From $283
         

9.0 (18 Reviews)
House
Stockbridge Village in Summer
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $265
         

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9.5 (2 Reviews)
House
Tranquil 3 BR Stockbridge House with Private Deck!
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $331
         

10.0 (1 Review)
Cottage
157 m² Cabin ∙ 4 bedrooms ∙ 8 guests
  • 1689 ft² Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $222
         

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8.8 (1006 Reviews)
Hotel
The Red Lion Inn
  • Air Conditioner
  • Pool
  • TV

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Property Image From $454
         

10.0 (128 Reviews)
House
Location! Location! Berkshire Glamour (and comfort) Meets Town And Country
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $314
         

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9.3 (9 Reviews)
Bed & Breakfast
Stockbridge Country Inn
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $1,180
         

10.0 (102 Reviews)
House
A Grand property in Historic Stockbridge
  • Air Conditioner
  • Parking
  • TV

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Property Image From $224
         

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9.0 (2 Reviews)
House
Cozy Stockbridge Cabin - Walk to Beach and Lake!
  • Parking
  • View
  • Ocean View

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Property Image From $335
         

10.0 (64 Reviews)
House
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $407
         

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8.0 (1 Review)
House
8 Mi to Tanglewood and Butternut Ski Spacious Home!
  • Parking
  • Pet Friendly
  • Security/Safety

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Property Image From $424
         

10.0 (29 Reviews)
House
Stockbridge Home, Come Experience The Berkshires!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $310
         

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7.4 (6 Reviews)
House
Lakefront Berkshires Retreat with Deck, Dock and Boat!
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $640
         

10.0 (27 Reviews)
House
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $259
         

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5.4 (63 Reviews)
Bed & Breakfast
The Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $588
         

10.0 (22 Reviews)
House
Secluded Family Home in Serene Stockbridge Woods
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $430
         

10.0 (16 Reviews)
House
Classic Stockbridge Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Visittheus makes it easy to compare the best listings on Visittheus homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Visittheus 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

Visittheus 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