Chesterfield Vacation Rentals

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Check prices for these dates

Tonight
Jun 16 - Jun 17
Tomorrow
Jun 17 - Jun 18
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Chesterfield

comfort, luxury, privacy
Fridge, microwave, oven, stovetop

comfort, luxury, privacy

9.8 out of 10, Exceptional, (60)
"My wife and I were only there for one night but will definitely stay at this property again in the future, communication was quick and friendly and the apartment was clean and cozy!!!"
comfort, luxury, privacy
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is ￥17,144
￥22,368 total
includes taxes & fees
Jun 22 - Jun 23
Deluxe Queen Room with 2 Queen Beds
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (30)
"Perfect place to stay while skiing Berkshire East! Clean, spacious, and beautiful surroundings!"
The price is ￥57,628
￥84,326 total
includes taxes & fees
Jun 22 - Jun 23
Bear Creek Cabin
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (4)
"Great property! Thank you for a wonderful stay."
The price is ￥35,873
￥65,818 total
includes taxes & fees
Jun 17 - Jun 18
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Charming 1-bedroom apartment in wonderful Lenox Dale
Exterior

Charming 1-bedroom apartment in wonderful Lenox Dale

10.0 out of 10, Exceptional, (1)
"I was thru-hiking the AT and had to get out of some bad weather. This place isn’t trail adjacent but it was worth the cab ride. Quiet, clean, laundry, easy check-in, well-stocked amenities, comfortable bed. Much better option than nearby hotels. Lucky to have found it when I needed it. "
Charming 1-bedroom apartment in wonderful Lenox Dale
The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (189)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Cozy Home in Holyoke with 3 bedrooms
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (6)
"Wonderful stay. Veronica was so kind and super responsive. The house was a great size and have everything we needed. We stayed there with 2 adults and 2 toddlers under 3. It was plenty of space. And a great location to all the area had to offer, museums, fun restaurants in North Hampton, etc. Would definitely stay again. "
The price is ￥18,729
￥46,670 total
includes taxes & fees
Jun 23 - Jun 24
Cozy Home in Holyoke with 3 bedrooms
Charming Apt in 18th c Berkshire Farmhouse
Miscellaneous

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (32)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is ￥19,449
￥29,910 total
includes taxes & fees
Jun 17 - Jun 18
Charming Apt in 18th c Berkshire Farmhouse
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (57)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Easthampton Apartment Near Breweries & Rail Trail!
Interior

Easthampton Apartment Near Breweries & Rail Trail!

9.6 out of 10, Exceptional, (14)
"Really cute house with all the amenities needed for our stay. "
Easthampton Apartment Near Breweries & Rail Trail!
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior

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

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Fireplace, books

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

9.6 out of 10, Exceptional, (32)
"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
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (215)
"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
Berkshire Lake at the Pillow, and EV!
Fridge, microwave, oven, stovetop

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."
Berkshire Lake at the Pillow, and EV!
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
1 bedroom, WiFi

Elm Suite with a Private Bathroom in front of Smith College Quadrangle

9.8 out of 10, Exceptional, (16)
"We really enjoyed staying at Elm Street. It convenient to the events we wanted to go to. It was clean bright and cheerful. Easy to enterHost was helpful and responsiveLove to stay there again"
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is ￥19,449
￥52,463 total
includes taxes & fees
Jun 17 - Jun 18
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
The Creation Station is a cozy place so make yourself at home.
Outdoor dining

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

10.0 out of 10, Exceptional, (65)
"This was our second time staying here and we had a great time!"
The price is ￥25,933
￥39,911 total
includes taxes & fees
Jun 18 - Jun 19
The Creation Station is a cozy place so make yourself at home.
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
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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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?

Deluxe Queen Room with 2 Queen Beds: Visitors like this Chesterfield vacation home rental. It is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay.

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 Gorge Reservation and Silvio O. Conte National Fish and Wildlife Refuge 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.