Holiday Rentals in Chesterfield

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Holiday Rentals in Chesterfield

Charming Chicopee Getaway

Chicopee
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. "
United States
Tamara S.
The price is €239
includes taxes & fees
2 Dec - 3 Dec
Charming Chicopee Getaway

Cozy Home in Holyoke with 3 bedrooms

Holyoke
9.6 out of 10, Exceptional, (10)
"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!! "
United States
Carrie M.
The price is €287
includes taxes & fees
13 Nov - 14 Nov
Cozy Home in Holyoke with 3 bedrooms

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (43)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is €179
includes taxes & fees
9 Nov - 10 Nov
Lovely 2nd Floor Apartment

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Perfect take out cafe across the street, was very comfortable would stay again for sure"
United States
Christopher
Cozy Rustic Apt in 18th c Berkshire Farmhouse

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

Easthampton Ma.
10.0 out of 10, Exceptional, (70)
"A very short but a really fun stay. Great location to just relax and get away from it all."
United States
Naseem P.
The price is €248
includes taxes & fees
10 Nov - 11 Nov
The Creation Station is a cozy place so make yourself at home.

Humble home with free breakfast

Chicopee
5.4 out of 10, (3)
"This host cancelled my booking 3 hours after our check in time. We had already arrived and were left stranded with no where to stay."
United States
Kathleen D.
The price is €287
includes taxes & fees
1 Dec - 2 Dec
Humble home with free breakfast

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

Greenfield
10.0 out of 10, Exceptional, (1)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is €183
includes taxes & fees
12 Nov - 13 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Townhouse with Pool Table - Renovated w/ King Bed

Chicopee
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
The price is €341
includes taxes & fees
13 Nov - 14 Nov
Townhouse with Pool Table - Renovated w/ King Bed

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

Hinsdale
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is €371
includes taxes & fees
10 Nov - 11 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"
United States
Jennifer F.
The price is €285
includes taxes & fees
6 Dec - 7 Dec
Home in the Woods

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €335
includes taxes & fees
18 Nov - 19 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Granby
9.4 out of 10, Exceptional, (18)
"Clean and easy to check in. Nick was easy to communicate with."
United States
Jeff M.
The price is €237
includes taxes & fees
13 Nov - 14 Nov
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

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

Amherst
9.2 out of 10, Wonderful, (15)
"Great spot. Super close to UMass Amherst which is where we were commuting back and forth from for tournament. Felt very private and appliances and games were amazing! "
United States
Kate B.
The price is €309
includes taxes & fees
10 Nov - 11 Nov
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Penthouse Apartment on Park Street

2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"We had a wonderful relaxing stay in this gorgeous place. The listing is just as described, natural light filled, high ceilings, on the top floor, comfortable bedding, and a thoughtful host. Lea left the A/C on, a bottle of water in the fridge, lots of good coffee, and even some hot cocoa packets for our son. The boba shop right downstairs was awesome and had fun gift items. There is a diner next door and some fantastic restaurants 15-20 minutes away. Very convenient to Mass MOCA and...
United States
Teresa M.
Penthouse Apartment on Park Street

2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls
2 Twin beds on 1st floor with En-suite bathroom.

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (9)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is €348
includes taxes & fees
19 Nov - 20 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Couples 2 Bedroom Retreat-Close to Shelburne Falls

Colrain
10.0 out of 10, Exceptional, (4)
"We had everything we needed for a fun and relaxing family get away. We loved how close it was to great restaurants and activities like rafting, zip lining, and the mountain coaster. The kitchen is fully stocked and everything was clean and well organized.Erica and Casey were great hosts and so helpful in answering any and all of our questions before check in. We will definitely be back! "
United States
Heather B.
The price is €333
includes taxes & fees
11 Nov - 12 Nov
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (141)
"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."
United States
Nicole K.
The price is €323
includes taxes & fees
9 Nov - 10 Nov
Big farmhouse in the foothills of the Berkshires

Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough
9.0 out of 10, Wonderful, (22)
"Very nice. Attending a wedding in the area and really needed a place to get dressed and return to sleep. This fit the bill perfectly. Clean and comfortable we enjoyed our visit. Need to come back and visit the many sites in the area."
United States
Margaret K.
Bright Boho Apt in 18th c Berkshire Farmhouse

Cozy Valley View Post & Beam Villa!

Whately
10.0 out of 10, Exceptional, (7)
"Thanks for a great stay"
United States
Andrea M.
Cozy Valley View Post & Beam Villa!
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

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as €179 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chesterfield has to offer?

Amore Estate - beautiful room with many places to explore and relax in.: This holiday home rental outside of Chesterfield offers an outdoor pool, a BBQ 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 that 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 holiday rental in Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family getaway.