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Compare 164 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 842 total
includes taxes & fees
21 Apr - 22 Apr
Berkshire Village Carriage House - Super Private!!

Author Stephen Oates Once Owned

8.0 out of 10, Very Good, (1)
"The house is very close to Amherst on a quiet street. Plenty of room, comfortable beds, and well supplied. We’d stay again! "
The price is SAR 859
SAR 1,568 total
includes taxes & fees
21 Apr - 22 Apr
Author Stephen Oates Once Owned

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (98)
"We were in Amherst to watch college baseball. The place was very close to the college, super comfortable and well stocked. Communication with the owner was great and we greatly appreciated the complimentary snacks, including eggs and oatmeal for breakfast. We hope to come back next year. Thank you! "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

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

10.0 out of 10, Exceptional, (71)
"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

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"Beautiful house in idyllic setting. Great host- we’ll be back!"
Peace and quiet on the lake

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.8 out of 10, Exceptional, (11)
"Great overnight stay! "
The price is SAR 619
SAR 1,083 total
includes taxes & fees
27 Apr - 28 Apr
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.0 out of 10, Wonderful, (4)
"We were really only at the house for the late evenings, nights, and mornings. We found the kitchen well stocked to make breakfast (we bought the groceries). The beds were comfortable. Only a couple minor issues that we just handled. The temperature control was preprogrammed to go to 50 degrees in the evening and overnight. We couldn't seem to reprogram it; however, did get it to kick up warmer about midnight or so. The shower in the main floor bathroom was hard to get turned off so the...
Owl's Nest - Cozy Westfield Home w/ Fire Pit

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"
Mountain Blossom Retreat by Evergreen Home

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (7)
"Lovely, spacious farmhouse. Well appointed and comfortable. Highly recommend. "
Historic Farmhouse Near Mountains & Colleges!

Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

9.6 out of 10, Exceptional, (30)
"Great place to stay. House was spacious, very clean, and well maintained "
Granby Home w/ Deck < 1/2 Mi to Aldrich Lake!

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (2)
Lakeside 5-BR Home in Idyllic Berkshires

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (19)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is SAR 484
SAR 809 total
includes taxes & fees
22 Apr - 23 Apr
Lovely 2nd Floor Apartment

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (28)
"perfect size for group of 7 adults...Good location especially for snow shoeing....cross country sking...enjoyed being in berkshires..."
The Meadows House @ Otis Ridge w/ 7-person hot tub

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is SAR 893
SAR 1,727 total
includes taxes & fees
28 Apr - 29 Apr
Charming 4Bds+1crib house with patio Amherst Center
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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Other property types in Chesterfield

comfort, luxury, privacy

9.8 out of 10, Exceptional, (58)
"Our stay was great. The space was comfortable and cozy. Was nice to have a kitchen to cook a little and they included fresh eggs with other snacks to make it welcoming. "
comfort, luxury, privacy

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is SAR 409
SAR 541 total
includes taxes & fees
21 Apr - 22 Apr
Deluxe Queen Room with 2 Queen Beds

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature
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.