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Compare 124 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 548
SAR 839 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is SAR 563
SAR 973 total
includes taxes & fees
1 Dec - 2 Dec
Cozy apartment located in quiet Williamsburg

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (15)
"Excellent communication with owner, answered all questions immediately via text when we were onsite. Well maintained property with great basement for hanging out as a family. "
Massachusetts Vacation Rental w/ Deck

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
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!

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (82)
"My mom and I did a mother/daughter trip to the Berkshires in October. Everything about this property is perfect! Location was 5/10 min from groceries/restaurants but felt like we were in the middle of nowhere. The house itself was very clean and so comfortable (the bed felt like a dream)! We spent our days exploring the surrounding towns and our evenings relaxing at he house. We saw deer in the mornings and 2 bald eagles! Thank you for the incredible stay!! "
Hearts Desire is a furnished whole house in a small, colorful garden center.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (19)
"This VRBO rental is adorable, clean, bright, and airy, and the location is perfect. The moment we opened the door, it felt right. The host, Kevin, did fantastic with the recent renovations, utilizing the space design and functionality. The home is equipped with all the amenities you need, items considered with comfort. I loved the designated coffee/tea nook area, offering both selections for your enjoyment. We sat outside on the deck off the kitchen and enjoyed the view of the fall foliage while...
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (82)
"Perry was awesome and easy to connect with. Beds were all very comfortable and there are 2 large bathrooms easy to share with a big family. Everything is labeled in the house and it makes it so easy to do everything. We will look forward to staying here in the future! "
Plainfield House in a 10,000 acre state forest and private pond

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"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

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (129)
"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "
Hadley Amherst Location.Explore the Valley Colleges!

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

9.8 out of 10, Exceptional, (95)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is SAR 545
SAR 776 total
includes taxes & fees
1 Dec - 2 Dec
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is SAR 721
SAR 1,326 total
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires

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

10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is SAR 676
SAR 1,053 total
includes taxes & fees
2 Dec - 3 Dec
The Creation Station is a cozy place so make yourself at home.

Spacious Historic Home in the Berkshires!

9.6 out of 10, Exceptional, (5)
"This lovely home was ideal for my family of 8: my children and their spouses, two grandchildren, myself and two pups. The beds were plentiful and comfortable. The house, while old, was newly remodeled, adding modern appliances to the charm of the original building. Very bright and spacious in a quiet neighborhood, convenient to Lenox, Tanglewood, and other special towns. I highly recommend this home to anyone looking for a pleasant retreat. We loved every minute!"
Spacious Historic Home in the Berkshires!

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

10.0 out of 10, Exceptional, (33)
"Nestled very quietly in the woods, this elegant home has everything you need for comfort."
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (12)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East

Lakeside 5-BR Home in Idyllic Berkshires

Lakeside 5-BR Home in Idyllic Berkshires

The Freckled Hen's Berkshire Nest

10.0 out of 10, Exceptional, (71)
"This is the 2nd time we stayed at this property, this time for 6 weeks. Property is conveniently located to major attractions, hiking, charming towns. The main bedroom is located on the first floor, perfect for us; our guests had complete privacy on the 2nd floor. The owner is responsive to guests’ needs and went as far as to order a step stool so i could reach the upper shelves. Prior to its arrival, i located one in the basement. Nancy even picked up our mail in the post office. "
The Freckled Hen's Berkshire Nest
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

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 548
SAR 839 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"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
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.