Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chesterfield vacation homes

Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (14 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is CA $178
CA $452 total
includes taxes & fees
Mar 19 - Mar 20
Cozy Home in Holyoke with 3 bedrooms
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is CA $159
CA $277 total
includes taxes & fees
Mar 1 - Mar 2
Lovely 2nd Floor Apartment
3 bedrooms, desk, iron/ironing board, travel crib

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (12 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is CA $274
CA $565 total
includes taxes & fees
Mar 15 - Mar 16
Townhouse with Pool Table - Renovated w/ King Bed
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is CA $246
CA $467 total
includes taxes & fees
Mar 6 - Mar 7
Big farmhouse in the foothills of the Berkshires
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is CA $246
CA $417 total
includes taxes & fees
Mar 2 - Mar 3
3-bedroom house in beautiful Berkshires, close to amenities!
Fridge, microwave, oven, stovetop

Colrain Spring into Adventure HotTub AirHockey Firepit

Colrain Spring into Adventure HotTub AirHockey Firepit
Colrain
9.8 out of 10, Exceptional, (47 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is CA $387
CA $888 total
includes taxes & fees
Mar 2 - Mar 3
Colrain Spring into Adventure HotTub AirHockey Firepit
Smart TV, books

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is CA $243
CA $570 total
includes taxes & fees
Mar 19 - Mar 20
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is CA $368
CA $677 total
includes taxes & fees
Feb 28 - Mar 1
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Dining

Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat
Charlemont
The price is CA $467
CA $905 total
includes taxes & fees
Mar 2 - Mar 3
Charlemont Chalet - A 15 Acre Private Retreat
Interior

Luxury Retreat inAmherst

Luxury Retreat inAmherst
Amherst
10.0 out of 10, Exceptional, (1 review)
"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."
United States
Robert
The price is CA $739
CA $1,161 total
includes taxes & fees
Mar 2 - Mar 3
Luxury Retreat inAmherst
Smart TV, fireplace, books

Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat

Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is CA $352
CA $887 total
includes taxes & fees
Mar 1 - Mar 2
Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is CA $219
CA $582 total
includes taxes & fees
Mar 2 - Mar 3
Riverbend Berkshire East Basecamp - 3 bedrooms available
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is CA $354
CA $755 total
includes taxes & fees
Mar 2 - Mar 3
Treetop Hideaway in Tyringham
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is CA $246
CA $626 total
includes taxes & fees
Mar 1 - Mar 2
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Dining

King Bed w/ Game Room near Massmutual w/ Riverview

King Bed w/ Game Room near Massmutual w/ Riverview
Chicopee
The price is CA $427
CA $813 total
includes taxes & fees
Mar 1 - Mar 2
King Bed w/ Game Room near Massmutual w/ Riverview
Dining

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass

Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Amherst
10.0 out of 10, Exceptional, (9 reviews)
"Perfect location, clean house, great for families with kids!"
United States
Emily Robustelli K.
The price is CA $614
CA $1,263 total
includes taxes & fees
Mar 1 - Mar 2
Spacious 5-Bedroom Home with Game Room in Amherst - Mins to UMass
Interior

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, attentive host. Location is as peaceful as can be. "
United States
Rick M.
The price is CA $470
CA $859 total
includes taxes & fees
Mar 2 - Mar 3
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Overall pleasant stay; great facilities, staff, and location"
Casey 2-night trip
Posted 3 days ago
Berkshire Mountain Lodge

Find out more about Chesterfield

Chesterfield Vacation Homes information

Number of reviews
295
Accommodation
148 Vacation Homes
Lowest Price
CA $277
Highest Price
CA $1,263

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