Chesterfield Holiday Rentals

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday Rentals in Chesterfield

Fridge, microwave, oven, stovetop
Charming Chicopee Getaway
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. "
United States
Tamara S.
The price is HK$777
HK$2,164 total
includes taxes & fees
11 Nov - 12 Nov
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.2 out of 10, Wonderful, (15)
"Great property! Thank you for a wonderful stay."
United States
David
The price is HK$1,014
HK$2,391 total
includes taxes & fees
22 Oct - 23 Oct
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms
Cozy Home in Holyoke with 3 bedrooms
9.6 out of 10, Exceptional, (10)
"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."
United States
Eric W.
The price is HK$1,010
HK$2,516 total
includes taxes & fees
27 Oct - 28 Oct
Cozy Home in Holyoke with 3 bedrooms
Fridge, microwave, oven, stovetop
Townhouse with Pool Table - Renovated w/ King Bed
Townhouse with Pool Table - Renovated w/ King Bed
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 HK$1,398
HK$2,988 total
includes taxes & fees
22 Oct - 23 Oct
Townhouse with Pool Table - Renovated w/ King Bed
Property grounds
The Creation Station is a cozy place so make yourself at home.
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (70)
"This was our second time staying here and we had a great time!"
United States
Andy L.
The price is HK$1,398
HK$2,178 total
includes taxes & fees
22 Oct - 23 Oct
The Creation Station is a cozy place so make yourself at home.
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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 HK$1,258
HK$3,098 total
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Interior
Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (40)
"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 HK$902
HK$1,580 total
includes taxes & fees
27 Oct - 28 Oct
Lovely 2nd Floor Apartment
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"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 HK$1,245
HK$3,056 total
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Private kitchen
Humble home with free breakfast
Humble home with free breakfast
7.0 out of 10, Good, (2)
The price is HK$1,041
HK$2,500 total
includes taxes & fees
17 Nov - 18 Nov
Humble home with free breakfast
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 HK$1,293
HK$3,302 total
includes taxes & fees
22 Oct - 23 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Dining
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Couples 2 Bedroom Retreat-Close to Shelburne Falls
10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
The price is HK$1,321
HK$2,890 total
includes taxes & fees
26 Oct - 27 Oct
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Property grounds
Big farmhouse in the foothills of the Berkshires
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!"
United States
Jon O.
The price is HK$1,554
HK$2,825 total
includes taxes & fees
22 Oct - 23 Oct
Big farmhouse in the foothills of the Berkshires
Oven, stovetop, dishwasher
Button's Modern Luxury Walkup Downtown Northampton
Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
United States
Meghan C.
The price is HK$1,942
HK$3,913 total
includes taxes & fees
4 Nov - 5 Nov
Button's Modern Luxury Walkup Downtown Northampton
Terrace/patio
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is HK$1,515
HK$2,209 total
includes taxes & fees
23 Oct - 24 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Fridge, microwave, oven, stovetop
Historic downtown house. Unscented products and sustainability practices.
Historic downtown house. Unscented products and sustainability practices.
10.0 out of 10, Exceptional, (5)
"It’s a beautiful home that worked for our stay as a family "
United States
Camilo W.
The price is HK$2,447
HK$4,729 total
includes taxes & fees
27 Oct - 28 Oct
Historic downtown house. Unscented products and sustainability practices.
Games room
Park Street Penthouse Apartment
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (12)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is HK$608
HK$1,521 total
includes taxes & fees
27 Oct - 28 Oct
Park Street Penthouse Apartment
Exterior
Bear Creek Cabin
Bear Creek Cabin
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,107
HK$4,651 total
includes taxes & fees
22 Oct - 23 Oct
Bear Creek Cabin
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is HK$2,331
HK$3,245 total
includes taxes & fees
22 Oct - 23 Oct
Bungalow in the Berkshires
Fridge, microwave, oven, stovetop
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
9.4 out of 10, Exceptional, (18)
"Great overnight stay! "
United States
Carrie M.
The price is HK$1,154
HK$2,073 total
includes taxes & fees
22 Oct - 23 Oct
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Fast and easy check in"
ALTIERI 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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

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.