Search the Best Cabins in Chesterfield

Upfront pricing

Our total price for your stay includes taxes and fees

Treat yourself

Save 10% or more on over 100,000 hotels worldwide with Member Prices

Learn about One Key

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Cabin Rentals in Chesterfield

Cozy cabin with a wrap-around porch and large windows offering a serene wooded setting.

"Loved our stay. "

Situated among lush greenery, this charming cabin offers a peaceful retreat with a porch and staircase leading to the entrance.

"Great"

Situated in a wooded area, this charming house features a front porch and a small garden with plants and a decorative pumpkin.

"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"

Surrounded by lush trees, this cabin features a spacious porch and a covered area with multiple windows.

"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! "

Escape to a serene forest retreat with a cozy cabin-style hotel, blending seamlessly into its natural surroundings.

"Adorable cabin with a central location to see everything in the Pioneer Valley/ Berkshires/Greater Springfield areas. The cabin is perfect for playing games, fishing, exploring the nearby lake and state parks or just plain relaxing! Be sure to bring marshmallows for toasting in the fire pit. Enjoy!"

Stylish log cabin with a central entrance and two windows on each side, set amidst a well-manicured lawn.

"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"

Situated in a secluded forest, this cabin offers a simple, two-story retreat with a flat roof and a small porch.

"We had a wonderful stay. The cabin was clean and comfortable! "

Situated in a forested area, this cabin features a spacious porch, large windows, and a steeply pitched roof.

"Enjoyed our stay"

$539 nightly

Aug 11 - Aug 12

Total includes taxes and fees

Situated in a forested area, this cabin-style building features a triangular roof and large windows, surrounded by a grassy landscape with scattered leaves.

"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "

"Great location and nice house "

Situated in a forested area, this cabin features a balcony for outdoor relaxation and a gravel pathway leading to the entrance.

"We had a wonderful stay in this adorable a frame!! Super cozy :)"

Cozy cabin nestled among the trees, offering a peaceful retreat with a prominent chimney and large windows.

"Lovely cottage. Very clean. Everything we needed. We had a great time!"

"Our host was a great communicator and very generous with the amenities (i.e., coffee pods, kayaks, life jackets, activities for kids... I could go on.) Check in was a breeze and flexible. The accommodations were clean and comfortable. There was an info board with helpful info for our stay. Our family loved the lake access and spent hours swimming and jumping off the floating dock. Neighbors we met at the beach were also super friendly. We def will come again. "

Surrounded by lush trees, this cabin offers a serene escape amidst nature.

"Wonderful accommodation."

"The cabin is charming, rustic, and a perfect getaway for a birthday or romantic weekend trip.The pollinator garden is truly a delight, and I loved watching them in the morning. The garden has even motivated my partner and I to start one at home.I wish that the mosquitoes were not present as well, but they are to be expected during the summer in MA.Overall, the stay was amazing. Marci was super sweet and left some nice gifts for my birthday. I definitely want to have another stay here again!"

Surrounded by lush greenery and tall trees, this serene stone structure offers a peaceful retreat.

Cozy cabin with a front porch and grill area, perfect for outdoor cooking and relaxation.

"The Shelburne cabin was a great home base for a getaway in the Berkshires. The cabin offered a great kitchen space, ample sleeping for a family of 5 and a wonderful field for hiking. Although very private, my family with three teenage girls would have been more comfortable if there was a shade in the bathroom and rear sleeping area."