Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Chesterfield vacation homes

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
The price is CA $162
CA $283 total
includes taxes & fees
Jun 17 - Jun 18
Lovely 2nd Floor Apartment
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is CA $182
CA $265 total
includes taxes & fees
Jun 11 - Jun 12
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $203
CA $525 total
includes taxes & fees
Jun 10 - Jun 11
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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, (17 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is CA $236
CA $527 total
includes taxes & fees
Jun 22 - Jun 23
Cozy Home in Holyoke with 3 bedrooms
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $167
CA $299 total
includes taxes & fees
Jun 11 - Jun 12
Private bed with En-suite bathroom Marigold Room
1 bedroom, desk, iron/ironing board, travel crib

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (75 reviews)
"Host was very accommodating."
United States
Christopher K.
The price is CA $251
CA $393 total
includes taxes & fees
Jun 22 - Jun 23
The Creation Station is a cozy place so make yourself at home.
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $223
CA $550 total
includes taxes & fees
Jun 10 - Jun 11
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Outdoor dining

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is CA $114
CA $453 total
includes taxes & fees
Jun 17 - Jun 18
Real Estate: Therapy - Lake, Laundry, Love it
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, (16 reviews)
"The house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
The price is CA $304
CA $645 total
includes taxes & fees
Jun 15 - Jun 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, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is CA $251
CA $476 total
includes taxes & fees
Jun 28 - Jun 29
Big farmhouse in the foothills of the Berkshires
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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 $403
CA $820 total
includes taxes & fees
Jun 10 - Jun 11
Treetop Hideaway in Tyringham
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 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 $330
CA $862 total
includes taxes & fees
Jun 10 - Jun 11
5BR Berkshire Home Mins To The Mountain
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (49 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is CA $364
CA $861 total
includes taxes & fees
Jun 10 - Jun 11
Spacious 5BR w/ Hot Tub & Games
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 $438
CA $772 total
includes taxes & fees
Jun 11 - Jun 12
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"It was a lovely four day stay. There was everything we needed in the large kitchen. The livingroom was comfortable and spacious. We especially enjoyed the back deck and the view of the mountains. If we return to the area, we'll definitely stay here again."
United States
Marianne B.
The price is CA $282
CA $645 total
includes taxes & fees
Jun 12 - Jun 13
Riverbend Berkshire East Basecamp - 3 bedrooms available
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
"rented for 2 nights. Apt was clean and climate control worked as expected. Nicely equipped location is good."
Andrew 2-night trip
Posted 2 hours ago
Berkshire Mountain Lodge

Find out more about Chesterfield

Chesterfield Vacation Homes information

Number of reviews
383
Accommodation
151 Vacation Homes
Lowest Price
CA $265
Highest Price
CA $862

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