Chesterfield Vacation Rentals

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Aug 3 - Aug 4
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Aug 4 - Aug 5
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Aug 8 - Aug 10
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Aug 15 - Aug 17

Vacation Rentals in Chesterfield

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Enjoy cooking in this well-lit kitchen with a central island, stainless steel appliances, and a brick backsplash.

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

9.0 out of 10, Wonderful, (6)
"Great property! Thank you for a wonderful stay."
The price is ￥27,711
￥55,322 total
includes taxes & fees
Aug 11 - Aug 12
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Easthampton Vacation Rental - Walk to Breweries!
Enter a cozy space with a comfortable room featuring a dresser and TV.

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (21)
"Our group had a wonderful time and we will not hesitate to book again in the future. The place was exceptionally clean, well appointed, and very comfortable. Overall it was a great experience! "
Easthampton Vacation Rental - Walk to Breweries!
The Clearing - Quiet - Close To Nature
Surrounded by a serene lawn and a tranquil pond, this peaceful setting offers a serene escape.

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (192)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Surrounded by lush trees, this cabin features a spacious porch and a covered area with multiple windows.

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (217)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is ￥17,113
￥29,654 total
includes taxes & fees
Aug 4 - Aug 5
Lovely 2nd Floor Apartment
Charming Chicopee Getaway
Kitchen features a white stove, cabinetry, and a coffee maker.

Charming Chicopee Getaway

The price is ￥18,867
￥45,227 total
includes taxes & fees
Sep 2 - Sep 3
Charming Chicopee Getaway
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is ￥14,593
￥19,593 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
comfort, luxury, privacy
Effortlessly prepare meals in this well-equipped kitchen featuring a refrigerator, dishwasher, microwave, and oven.

comfort, luxury, privacy

9.8 out of 10, Exceptional, (69)
"Clean and comfortable property! Perfect for visiting the Amherst area. It was easy to get to the Dickinson House and the Eric Carle Museum. Would definitely stay again. "
comfort, luxury, privacy
Charming Apt in 18th c Berkshire Farmhouse
Two single beds with bedside tables and lamps, set against a rustic wooden wall and a textured rug.

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (34)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is ￥19,899
￥30,602 total
includes taxes & fees
Aug 6 - Aug 7
Charming Apt in 18th c Berkshire Farmhouse
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is ￥29,480
￥53,596 total
includes taxes & fees
Aug 4 - Aug 5
Big farmhouse in the foothills of the Berkshires
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Relax in a spacious living area with a high ceiling and large windows offering views of the surrounding greenery.

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Escape to a secluded cabin surrounded by trees, with a picnic table and comfortable seating.

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

9.6 out of 10, Exceptional, (60)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Button's Modern Luxury Walkup Downtown Northampton
Oven, stovetop, dishwasher

Button's Modern Luxury Walkup Downtown Northampton

The price is ￥36,850
￥74,419 total
includes taxes & fees
Aug 5 - Aug 6
Button's Modern Luxury Walkup Downtown Northampton
Bear Creek Cabin
Situated in a forested area, this cabin features a spacious porch, large windows, and a steeply pitched roof.

Bear Creek Cabin

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
The price is ￥58,960
￥88,745 total
includes taxes & fees
Aug 11 - Aug 12
Bear Creek Cabin
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Relax in this serene room with a large bed, stone fireplace, and forest views.

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (43)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Situated in a wooded area, this cabin features a welcoming front porch and a serene, secluded environment.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Enjoy a functional kitchen with a central island, perfect for meal prep and dining.

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (80)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Amherst, Perfect Location, UMass, Smith, MHC!
Enjoy a quiet moment on the deck with a small table and two chairs, shaded by an umbrella.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (16)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!
Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great price for area with clean and spacious suites. Would be perfect if offered on site breakfast."
Barbara 1-night trip
Posted 4 hours ago
Berkshire Mountain Lodge

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?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : Visitors like this Chesterfield vacation home rental. It offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.