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

Airportexpresshotel - Vacation Rentals in Chesterwood

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 $374
         

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9.2 (107 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 $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 $269
         

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

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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 $200
         

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8.8 (1014 Reviews)
Hotel
The Red Lion Inn
  • Air Conditioner
  • Pool
  • TV

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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 $64
         

6.8 (1005 Reviews)
Hotel
Pleasant Valley Motel West 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 $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 $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 $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 $1,413
         

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New
House
Stockbridge Retreat with Pool and Hot Tub!
  • Parking
  • Pool
  • View

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Property Image From $1,342
         

New
House
Woodland Zen by AvantStay Modern Design Patio
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $474
         

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New
House
Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The Woods
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $360
         

New
House
Beautiful House in the Woods, Huge Yard, Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $354
         

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New
House
1 Mi to Dtwn Cottage with Large Yard in Stockbridge
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $308
         

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New
House
Classic Stockbridge Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $260
         

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New
House
Steps to Downtown Stockbridge Home with Patio!
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $203
         

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New
Apartment
2 Mi to Norman Rockwell Museum Stockbridge Apt!
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $308
         

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8.1 (288 Reviews)
Hotel
The Red Lion Inn
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $79
         

5.4 (116 Reviews)
Hotel
Pleasant Valley Motel West Stockbridge
  • Air Conditioner
  • Parking
  • Security/Safety

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

Airportexpresshotel 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