Chesterfield Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chesterfield Vacation Homes

Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is CA $159
CA $276 total
includes taxes & fees
Aug 13 - Aug 14
Lovely 2nd Floor Apartment
Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Step out onto the porch and enjoy the fresh air from the comfort of two chairs and a small table.

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

9.8 out of 10, Exceptional, (107)
"Booked this on a college tour with my daughters. Close to Amherst and easy to get to, clean, and cozy. Loved the homemade bread and fresh eggs left for us in the fridge!"
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is CA $275
CA $504 total
includes taxes & fees
Aug 10 - Aug 11
Big farmhouse in the foothills of the Berkshires
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Stunning two-story home with a gabled roof and inviting front porch.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (12)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Spacious Private Retreat Near Holyoke State Park!
Enjoy meals in the kitchen with a dining area featuring a table and chairs.

Spacious Private Retreat Near Holyoke State Park!

10.0 out of 10, Exceptional, (9)
"We stayed for a guys hunting trip and the place was what we needed after a long day"
Spacious Private Retreat Near Holyoke State Park!
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Enjoy meals and games in this kitchen with a central island and pool table.

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is CA $234
CA $511 total
includes taxes & fees
Aug 13 - Aug 14
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Situated in a wooded area, this cabin features a welcoming front porch and a serene, secluded environment.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Enjoy a functional kitchen with a central island, perfect for meal prep and dining.

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (81)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Quiet Cabin On Over 12 Acres Of Woods!
Cozy living space with a central island kitchen, spiral staircase, and comfortable seating area.

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (11)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Quiet Cabin On Over 12 Acres Of Woods!
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Relax in a serene outdoor space with a shaded table and chairs surrounded by lush greenery.

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
StrautmanHaus - All-Season Chalet at Berkshire East
Enjoy meals in this kitchen with an oven, microwave, and stove, adjacent to a dining area with a large window offering a view of the outdoors.

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (12)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East
Cabin Retreat in the Berkshire Woods
Cozy living area with a central staircase, comfortable seating, and dining space.

Cabin Retreat in the Berkshire Woods

Cabin Retreat in the Berkshire Woods
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
Situated on a lush lawn, this charming house features a wrap-around porch and a prominent gable roof.

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (27)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
The Creation Station is a cozy place so make yourself at home.
Explore the serene surroundings of this peaceful outdoor space, featuring a tranquil pond and lush greenery.

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

10.0 out of 10, Exceptional, (66)
"This was our second time staying here and we had a great time!"
The price is CA $247
CA $377 total
includes taxes & fees
Aug 18 - Aug 19
The Creation Station is a cozy place so make yourself at home.
Amore Estate - beautiful room with many places to explore and relax in.
Enjoy cooking in this well-equipped kitchen with a central island, white cabinetry, and a stainless steel range hood.

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (25)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Relax in a spacious living area with a high ceiling and large windows offering views of the surrounding greenery.

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Cozy Home in Holyoke with 3 bedrooms
Exterior detail

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (7)
"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "
The price is CA $247
CA $528 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Home in Holyoke with 3 bedrooms
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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Very clean room & bathrooms. Comfortable beds and bedding. "
Caitlin 1-night trip
Posted 19 hours ago
Tru by Hilton Chicopee Springfield