Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Chesterfield vacation rentals

Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is ￥18,181
￥31,505 total
includes taxes & fees
Jan 8 - Jan 9
Lovely 2nd Floor Apartment
Private kitchen
Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is ￥18,792
￥52,945 total
includes taxes & fees
Jan 14 - Jan 15
Welcoming 3-bedroom house- Gardner home
Fridge, microwave, oven, stovetop
Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (13)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is ￥20,358
￥50,378 total
includes taxes & fees
Jan 9 - Jan 10
Cozy Home in Holyoke with 3 bedrooms
Living area
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is ￥18,166
￥38,134 total
includes taxes & fees
Jan 8 - Jan 9
Penthouse Apartment on Park Street
Property grounds
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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, (35)
"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 ￥25,369
￥65,596 total
includes taxes & fees
Jan 8 - Jan 9
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
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 ￥22,832
￥58,914 total
includes taxes & fees
Jan 8 - Jan 9
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amherst
9.2 out of 10, Wonderful, (19)
"Great property! Thank you for a wonderful stay."
United States
David
The price is ￥35,094
￥65,963 total
includes taxes & fees
Jan 8 - Jan 9
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Desk, iron/ironing board, travel crib, WiFi
The Creation Station is a cozy place so make yourself at home.

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, (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 ￥28,188
￥43,381 total
includes taxes & fees
Jan 8 - Jan 9
The Creation Station is a cozy place so make yourself at home.
Living area
Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (2)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ￥21,767
￥31,800 total
includes taxes & fees
Jan 8 - Jan 9
Cozy 2-bedroom apartment in Chicopee
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
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 ￥25,087
￥61,782 total
includes taxes & fees
Jan 12 - Jan 13
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
3 bedrooms, desk, iron/ironing board, travel crib
Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (11)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is ￥28,188
￥60,227 total
includes taxes & fees
Jan 11 - Jan 12
Townhouse with Pool Table - Renovated w/ King Bed
Interior
Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (2)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ￥51,521
￥94,458 total
includes taxes & fees
Jan 11 - Jan 12
Button's Modern Luxury Walkup Downtown Northampton
Terrace/patio
Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is ￥35,235
￥73,994 total
includes taxes & fees
Jan 11 - Jan 12
Terrific 3-bedroom unit in charming Leverett with AC
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

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Granby
9.0 out of 10, Wonderful, (22)
"Great overnight stay! "
United States
Carrie M.
The price is ￥23,255
￥41,795 total
includes taxes & fees
Jan 8 - Jan 9
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails
Exterior
Bear Creek Cabin

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥62,640
￥93,760 total
includes taxes & fees
Jan 8 - Jan 9
Bear Creek Cabin
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (1)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ￥25,056
￥66,121 total
includes taxes & fees
Jan 8 - Jan 9
Riverbend Berkshire East Basecamp - 3 bedrooms available
Smart TV, books
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is ￥28,188
￥72,067 total
includes taxes & fees
Jan 8 - Jan 9
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Exterior detail
3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ￥31,148
￥51,760 total
includes taxes & fees
Jan 10 - Jan 11
3-bedroom house in beautiful Berkshires, close to amenities!
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

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

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is ￥13,781
￥27,463 total
includes taxes & fees
Jan 11 - Jan 12
2 Twin beds on 1st floor with En-suite bathroom.
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

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Room was great. Overnight staff that checked us in was so cheerful and kind."
Min Ji 1-night trip
Posted 10 hours ago
Comfort Inn & Suites

Find out more about 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 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Chesterfield vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Krug Sugarbush 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.