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Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home in Williamsburg
Hilltown Studio
Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.
$110 per night
Cabin in Williamsburg
A Peaceful Cabin minutes from Northampton
Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley and Amherst, then this cabin is perfect. Within walking distance you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.
$133 per night
Rental unit in Easthampton
Private Farm Apartment, Close to Everything - 1BR
Our farm is a quiet, 5+ acre haven one mile from the center of Easthampton and 8-12 minutes to Smith College/Northampton. It's a great base from which to explore all the restaurants, cultural and outdoor activities offered in the beautiful Pioneer Valley. The private apartment is on the first level of our rustic farmhouse and offers a kitchenette, living room, queen bedroom and bathroom. (An additional bedroom is also available-see separate listing for 2BR).
$82 per night

Other great vacation rentals in Chesterfield

Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
$225 per night
Home in Easthampton
Private Home~Old World Charm, Modern Conveniences
$125 per night
Cottage in Williamsburg
Charming Lakefront Front Cottage With Private Dock
$198 per night
Guesthouse in Northampton
Mill River Cottage (pet friendly!)
$105 per night
Private room in Huntington
Ancient Colony
$55 per night
Private room in Northampton
Warm Country Home Minutes from Town
$50 per night
Rental unit in Westhampton
1800’s farmhouse with beautiful outdoor area
$145 per night
Guest suite in Williamsburg
Happy Maples!
$119 per night
Barn in Northampton
E. Slate Carriage House
$89 per night
Private room in Williamsburg
A Place for Peace - suite w/full bath
$75 per night
Guest suite in Northampton
Separate apt, 1 mile from downtown, 1 guest only
$84 per night
Private room in Sunderland
Bright private suite minutes to Five College area
$82 per night