Chesterfield Vacation Rentals

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"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "

CA $328 total

includes taxes & fees

Jan 14 - Jan 15

"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"

"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...

"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."

CA $297 total

includes taxes & fees

Jan 12 - Jan 13

"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. "

"Great stay. Host lives to the right. Good spacious place. Quite. Clean. Easy to find from the road. We enjoyed our stay. Very comfortable. "

CA $412 total

includes taxes & fees

Jan 25 - Jan 26

"As advertised "

"Very nice place, clean, great communication. "

"Great location near restaurants and stores. House is "

CA $654 total

includes taxes & fees

Feb 7 - Feb 8

"Convenient location, comfortable."

CA $365 total

includes taxes & fees

Jan 11 - Jan 12

"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. "

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."

CA $549 total

includes taxes & fees

Jan 11 - Jan 12

"Highly recommend this house. Wonderful location, plenty of beds for a group. Great communication with the host."

"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "

"It was gorgeous, and we had a wonderful cozy time. "

Fridge, dishwasher, cookware/dishes/utensils, paper towels

"We had a lovely time staying here as a group for a birthday weekend, the location is great! "

"We enjoyed a long weekend at this beautiful home. We had plenty of room for us to spread out. The kitchen is well stocked. They had games in the basement which were an added bonus. The beds were comfortable. We enjoyed relaxing on the porch in the evenings. We would definitely stay here again."

"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "

"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!"