Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Chesterfield

Our top choices for Chesterfield vacation rentals

Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (39)
"We enjoyed our stay!!"
The price is ￥59,044
￥88,377 total
includes taxes & fees
Oct 5 - Oct 6
Bear Creek Cabin
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Terrace/patio

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

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (223)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Fridge, microwave, oven, stovetop

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

9.2 out of 10, Wonderful, (14)
"Great property! Thank you for a wonderful stay."
The price is ￥24,109
￥50,867 total
includes taxes & fees
Oct 6 - Oct 7
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is ￥17,278
￥29,940 total
includes taxes & fees
Sep 29 - Sep 30
Lovely 2nd Floor Apartment
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (200)
"The property was beautiful and well maintained.The home where we stayed was perfect and cozy."
The Clearing - Quiet - Close To Nature
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Fridge, microwave, oven, stovetop

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (23)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (65)
"Great value, so much better than all the touristy motels in the area!"
The price is ￥19,927
￥30,645 total
includes taxes & fees
Sep 26 - Sep 27
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake
comfort, luxury, privacy
Fridge, microwave, oven, stovetop

comfort, luxury, privacy

9.8 out of 10, Exceptional, (71)
"The stay was very peaceful and the host were very helpful in terms of communication "
comfort, luxury, privacy
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"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. "
The price is ￥16,668
￥42,537 total
includes taxes & fees
Oct 21 - Oct 22
Charming Chicopee Getaway
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Fridge, microwave, oven, stovetop

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2.0 star property
10.0 out of 10, Exceptional, (11)
"My husband and I and our little dog had an amazing stay in Dalton. The space was clean, perfectly decorated and comfortable! We only stayed a few days and wanted to stay so much longer! Coffee for the humans and frog toys and treats for Sully! Very convenient to all the Berkshires has to offer. Communication with the owner was prompt and always helpful!! Highly recommend and hope to return. "
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Outdoor dining

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

10.0 out of 10, Exceptional, (2)
"Great location & unique charming place!"
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

9.8 out of 10, Exceptional, (30)
"Hindsale-perfect little hideaway, minutes from where we needed to be. Harrison’s little home was equipped with amenities/tasteful luxuries, and cozy nooks. We all loved the loft-could not believe how large the space was! Hot tub nights-perfect ending:) Thank you, Harrison."
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is ￥29,764
￥53,169 total
includes taxes & fees
Sep 28 - Sep 29
Big farmhouse in the foothills of the Berkshires
Amherst, Perfect Location, UMass, Smith, MHC!
Outdoor dining

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (17)
"Everything was clean and comfortable. It was a perfect getaway."
Amherst, Perfect Location, UMass, Smith, MHC!
Cozy Home in Holyoke with 3 bedrooms
Terrace/patio

Cozy Home in Holyoke with 3 bedrooms

9.6 out of 10, Exceptional, (9)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
The price is ￥19,189
￥47,816 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Home in Holyoke with 3 bedrooms
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub
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

Quality Inn West Springfield

Quality Inn West Springfield

10/10 Excellent
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
Danielle 1-night trip
Posted 1 day ago
Quality Inn West Springfield

Find out more about Chesterfield

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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?

Amore Estate - beautiful room with many places to explore and relax in.: Visitors like this Chesterfield vacation home rental. It offers an outdoor pool, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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. Chesterfield Public Library and Chesterfield Town Hall 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.