Villa Bay - Vacation Rentals in Chesterwood

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From US $320

         

10.0 (92 Reviews)

House

Tranquil 3 BR Stockbridge House w/Private Deck!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Glendale

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From US $351

         

|

10.0 (2 Reviews)

House

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Stockbridge

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From US $462

         

|

9.2 (110 Reviews)

Bed & Breakfast

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Glendale

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From US $357

         

10.0 (13 Reviews)

House

Completely Renovated Historic Home in the Heart of the Berkshires

• Air Conditioner
• Parking
• TV

• Massachusetts
• Glendale

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From US $499

         

|

10.0 (1 Review)

House

Too Good AKA 2 Goodrich St

• Air Conditioner
• View
• Security/Safety

• Massachusetts
• Stockbridge

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From US $219

         

6.4 (22 Reviews)

Bed & Breakfast

Tanglewood Suites

• Air Conditioner
• Parking
• TV

• Massachusetts
• Stockbridge

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From US $316

         

9.0 (20 Reviews)

House

Stockbridge Village in Summer

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Stockbridge

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From US $265

         

|

9.5 (2 Reviews)

House

Tranquil 3 BR Stockbridge House with Private Deck!

• Parking
• Pet Friendly
• Accessibility

• Massachusetts
• Glendale

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From US $206

         

|

8.8 (1001 Reviews)

Hotel

The Red Lion Inn

• Air Conditioner
• Pool
• TV

• Massachusetts
• Stockbridge

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From US $450

         

10.0 (135 Reviews)

House

Location! Location! Berkshire Glamour (and comfort) Meets Town And Country

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• West Stockbridge

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From US $1,321

         

10.0 (104 Reviews)

House

A Grand property in Historic Stockbridge

• Air Conditioner
• Parking
• TV

• Massachusetts
• Stockbridge

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From US $285

         

10.0 (70 Reviews)

House

Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

• Air Conditioner
• Parking
• TV

• Massachusetts
• West Stockbridge

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From US $387

         

10.0 (30 Reviews)

House

Stockbridge Home, Come Experience The Berkshires!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Stockbridge

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From US $840

         

10.0 (29 Reviews)

House

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Stockbridge

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From US $454

         

10.0 (23 Reviews)

House

Secluded Family Home in Serene Stockbridge Woods

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Glendale

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From US $433

         

10.0 (17 Reviews)

House

Classic Stockbridge Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Glendale

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From US $271

         

10.0 (14 Reviews)

House

Stockbridge pied-à-terre

• Air Conditioner
• Parking
• TV

• Massachusetts
• Stockbridge

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From US $442

         

10.0 (13 Reviews)

House

Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay

• Air Conditioner
• Parking
• TV

• Massachusetts
• Housatonic

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From US $763

         

10.0 (11 Reviews)

House

Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

• Air Conditioner
• Parking
• TV

• Massachusetts
• Stockbridge

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From US $492

         

10.0 (8 Reviews)

House

Spacious & Modern Berkshires Getaway

• Air Conditioner
• Parking
• Balcony/Terrace

• Massachusetts
• Glendale

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From US $541

         

10.0 (4 Reviews)

House

Premier Stockbridge Retreat Near 3 Ski Resorts, Dining, Norman Rockwell & Lenox

• Air Conditioner
• Parking
• TV

• Massachusetts
• Stockbridge

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From US $443

         

10.0 (4 Reviews)

Cottage

1 Mi to Dtwn: Cottage w/Large Yard in Stockbridge

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Glendale

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From US $516

         

10.0 (3 Reviews)

House

Beautiful House in the Woods: Huge Yard, Hot Tub

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Glendale

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From US $440

         

10.0 (3 Reviews)

House

8 Mi to Tanglewood & Butternut Ski: Spacious Home!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Housatonic

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