Chesterfield Holiday Rentals

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Chesterfield holiday rentals

Interior
Peace and quiet on the lake

Holiday Home in Sherwood Forest

Peace and quiet on the lake
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Interior
Lovely 2nd Floor Apartment

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is HK$903
HK$1,566 total
includes taxes & fees
17 Dec - 18 Dec
Lovely 2nd Floor Apartment
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Holiday Home in Lanesborough

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
10.0 out of 10, Exceptional, (8)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Exterior detail
Hearts Desire is a furnished whole house in a small, colorful garden center.

Holiday Home in Lanesborough

Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (97)
"This was our third time at this property. We still love it and look forward to returning again."
United States
Lisa P.
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior detail
Elm Suite with a Private Bathroom in front of Smith College Quadrangle

Apartment in Northampton

Elm Suite with a Private Bathroom in front of Smith College Quadrangle
9.8 out of 10, Exceptional, (23)
"Gorgeous building, clean and cozy spot to stay. "
United States
Grace
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Terrace/patio
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Holiday Home in Amherst

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (111)
"Check in was easy breezy, communication with host was timely and helpful. It was perfect for our two day stay. Fresh eggs and homemade bread and Cushman's cafe close by wwre added treats!"
United States
Kelly S.
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Property grounds
Experience Three Sisters Sanctuary in Goshen, MA

Holiday Home in Goshen

Experience Three Sisters Sanctuary in Goshen, MA
2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
Fridge, microwave, oven, stovetop
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Apartment in Amherst

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.4 out of 10, Exceptional, (18)
"Great property! Thank you for a wonderful stay."
United States
David
The price is HK$1,744
HK$3,269 total
includes taxes & fees
17 Dec - 18 Dec
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Exterior
Bear Creek Cabin

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,113
HK$4,642 total
includes taxes & fees
17 Dec - 18 Dec
Bear Creek Cabin
Fridge, microwave, oven, stovetop
comfort, luxury, privacy

Apartment in Amherst

comfort, luxury, privacy
9.8 out of 10, Exceptional, (72)
"Great stay!"
United States
Shawn L.
comfort, luxury, privacy
Outdoor pool
The Clearing - Quiet - Close To Nature

Cottage in Cummington

The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (211)
"This was the perfect little home for my husband and I to stay for a few days while we visited the area. Loved it."
Canada
Andrea F.
The Clearing - Quiet - Close To Nature
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Holiday Home in Lenox

Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Fireplace, books
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

Holiday Home in Cummington

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
9.6 out of 10, Exceptional, (40)
"My friends and I had the most beautiful rainy weekend here to celebrate my 40th birthday. The spot was perfect for the 5 of us and the river was such a wonderful bonus to our peaceful trip!"
United States
Sarah R.
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,135
HK$2,910 total
includes taxes & fees
18 Dec - 19 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10)
"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$1,247
HK$2,975 total
includes taxes & fees
18 Dec - 19 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Property grounds
Hadley Amherst Location.Explore the Valley Colleges!

Holiday Home in Hadley

Hadley Amherst Location.Explore the Valley Colleges!
10.0 out of 10, Exceptional, (132)
"Such a wonderful property and amazing host! A convenient location to the area as well as shopping and beautiful bike/walking trail!Thank you Colleen!"
United States
John M.
Hadley Amherst Location.Explore the Valley Colleges!
Property grounds
The Creation Station is a cozy place so make yourself at home.

Holiday Home in Easthampton Ma.

The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,401
HK$2,156 total
includes taxes & fees
22 Dec - 23 Dec
The Creation Station is a cozy place so make yourself at home.
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Holiday Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
The price is HK$1,245
HK$3,234 total
includes taxes & fees
14 Jan - 15 Jan 2026
Riverbend Berkshire East Basecamp - 3 bedrooms available
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (34)
"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$1,324
HK$3,331 total
includes taxes & fees
17 Dec - 18 Dec
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Terrace/patio
Quintessential 6-BR Berkshires Lodge

Holiday Home in Becket

Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (17)
"Great weekend away. Thank you!"
United States
Karen P.
Quintessential 6-BR Berkshires Lodge
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
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
Dwight 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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  • 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 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?

Peace and quiet on the lake: This holiday home rental outside of Chesterfield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Chesterfield Gorge Reservation are a couple of lovely local spots to get outside and enjoy nature. Chesterfield Public Library and Westfield River 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.