Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Chesterfield vacation rentals

Apartment (1 Bedroom) | Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
2.5 star property
Holyoke
The price is ￥10,811
￥37,230 total
includes taxes & fees
May 11 - May 12
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is ￥18,191
￥31,697 total
includes taxes & fees
May 11 - May 12
Lovely 2nd Floor Apartment
Exterior

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (2 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is ￥9,714
￥37,611 total
includes taxes & fees
May 11 - May 12
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
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)
"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."
United States
Kelly Z.
The price is ￥28,202
￥43,577 total
includes taxes & fees
May 18 - May 19
The Creation Station is a cozy place so make yourself at home.
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥30,741
￥72,841 total
includes taxes & fees
May 10 - May 11
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 ￥19,601
￥28,895 total
includes taxes & fees
May 11 - May 12
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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 ￥27,106
￥60,379 total
includes taxes & fees
May 12 - May 13
Cozy Home in Holyoke with 3 bedrooms
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 ￥22,844
￥58,945 total
includes taxes & fees
May 10 - May 11
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Smart TV, books

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, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is ￥25,100
￥60,939 total
includes taxes & fees
May 17 - May 18
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior detail

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is ￥18,614
￥43,194 total
includes taxes & fees
May 13 - May 14
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is ￥16,216
￥30,189 total
includes taxes & fees
May 10 - May 11
Rose room Victorian home queen bed private bath
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥18,802
￥33,427 total
includes taxes & fees
May 27 - May 28
Private bed with En-suite bathroom Marigold Room
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (78 reviews)
"Great stay!"
United States
Shawn L.
The price is ￥19,037
￥28,265 total
includes taxes & fees
May 10 - May 11
comfort, luxury, privacy
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, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is ￥31,336
￥56,970 total
includes taxes & fees
May 11 - May 12
Big farmhouse in the foothills of the Berkshires
TV

Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4 reviews)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
The price is ￥15,847
￥43,540 total
includes taxes & fees
May 10 - May 11
Charming Chicopee Getaway
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful house, immaculate and cool space! Perfect overnight after catching a show at Shea Theater."
United States
Nicole C.
The price is ￥19,742
￥25,552 total
includes taxes & fees
May 18 - May 19
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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)
"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 ￥32,856
￥70,162 total
includes taxes & fees
May 10 - May 11
Townhouse with Pool Table - Renovated w/ King Bed
Outdoor dining

Historic downtown apartment. Unscented products and sustainability practices.

Historic downtown apartment. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (11 reviews)
"Quite a find in pricey Northampton. Within easy walking distance to restaurants and shops. Small but very comfortable. We didn't spend much time in the apartment, but it was perfect for what we needed."
United States
Jessica B.
The price is ￥28,829
￥53,204 total
includes taxes & fees
May 11 - May 12
Historic downtown apartment. Unscented products and sustainability practices.
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥9,025
￥46,660 total
includes taxes & fees
May 27 - May 28
Real Estate: Therapy - Lake, Laundry, Love it
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (48 reviews)
"Our family and friends loved everything about this home. It is better than pictures and so convenient to mountain. Easy check-in and great communication with Erika and Casey. We will definitely be back and try some warm weather adventures. "
United States
Brandy G.
Spacious 5BR w/ Hot Tub & Games
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

Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

8/10 Good
"Issues with key cards from numerous people that night."
Jennifer 1-night trip
Posted 2 hours ago
Red Roof Inn PLUS+ South Deerfield – Amherst

Find out more about Chesterfield

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Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we have vacation rentals near popular attractions in Chesterfield, or you can go with a secluded option if you want a relaxing place to stay. Chesterfield is known for its restaurants and shopping. Make sure you have time to check out the parks while you're in the area.

What are some of the best vacation rentals in Chesterfield?

Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Westfield River are a couple of lovely local spots to get outside and enjoy nature. Silvio O. Conte National Fish and Wildlife Refuge and Chesterfield Public Library are other places to visit while you're in town.

What’s a vacation rental in Chesterfield like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.