Best price vacation rentals in Chesterfield, MA, USA • 150 Listings
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Chesterfield, MA, USA Vacation Rentals | 

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5.0 (39)
Designer Guest Suite on Historic New England Homestead
Up to 5 guests
Airbnb$314
Vrbo$328
Average Nightly Rate
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5.0 (3)
A cozy rest in tiny home of a nest (downtown Northampton)
Up to 3 guests
Airbnb$90
Vrbo$96
Average Nightly Rate
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5.0 (38)
Low-scent, Northampton historic mill house
Up to 5 guests
Airbnb$218
Vrbo$244
Average Nightly Rate
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5.0 (182)
Bamboo: Spacious with Cedar Wet-room.
Up to 2 guests
Airbnb$150
Vrbo$150
Average Nightly Rate
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5.0 (274)
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Up to 6 guests
Airbnb$210
Vrbo$210
Average Nightly Rate
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5.0 (133)
Mountain View: Comfort and Calm.
Up to 4 guests
Airbnb$200
Vrbo$200
Average Nightly Rate
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4.9 (170)
Plainfield House in a 10,000 acre state forest and private pond
Up to 10 guests
Vrbo$237
Airbnb$270
Average Nightly Rate

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4.9 (43)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Up to 8 guests
Vrbo$480
Airbnb$490
Average Nightly Rate
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4.9 (44)
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Up to 6 guests
Airbnb$244
Vrbo$244
Average Nightly Rate

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4.6 (40)
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Up to 6 guests
Vrbo$272
Airbnb$276
Average Nightly Rate
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3.6 (17)
Historic Huntington Home - Walk to Westfield River
Up to 7 guests
Airbnb$214
Vrbo$217
Average Nightly Rate
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0.0 (0)
Furnished Rental monthly/weekly rental with discount!
Up to 5 guests
Airbnb$161
Vrbo$161
Average Nightly Rate
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5.0 (85)
Country Luxury in the Heart of the Berkshires
Up to 8 guests
Airbnb$76
Average Nightly Rate
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5.0 (74)
Beautiful Secluded Country House
Up to 12 guests
Airbnb$370
Average Nightly Rate
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5.0 (27)
Private Northampton Area Home on 8 Lush Acres
Up to 6 guests
Vrbo$116
Average Nightly Rate
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5.0 (66)
Haley House
Up to 8 guests
Airbnb$225
Average Nightly Rate
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5.0 (90)
Wood, sunshine & movies in best downtown location
Up to 5 guests
Airbnb$189
Average Nightly Rate
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5.0 (72)
The Glow Room at Indian Hollow
Up to 4 guests
Airbnb$250
Average Nightly Rate
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5.0 (160)
Clean, Sunny, Open Floor Plan near Smith College
Up to 6 guests
Airbnb$211
Average Nightly Rate
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5.0 (75)
Starlight Llama Bed & Breakfast - Solar Powered!
Up to 2 guests
Airbnb$130
Average Nightly Rate
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5.0 (141)
Lovely 1 Bedroom w private entrance
Up to 3 guests
Airbnb$82
Average Nightly Rate
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5.0 (20)
3 room suite with breakfast facilities in home
Up to 2 guests
Airbnb$90
Average Nightly Rate
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5.0 (91)
Upstairs at Deer Hill House
Up to 4 guests
Airbnb$100
Average Nightly Rate
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5.0 (227)
The Cottage Room Studio Apartment
Up to 2 guests
Airbnb$134
Average Nightly Rate
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5.0 (202)
Large Quirky Sunny Farmhouse Apartment
Up to 3 guests
Airbnb$99
Average Nightly Rate
  1. United States
  2. Massachusetts
  3. Chesterfield Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Chesterfield, MA, USA

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