Search the Best Cabins in Chesterfield

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23

Cabin Rentals in Chesterfield

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (224)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (39)
"We enjoyed our stay!!"
$536 nightly
The price is $599
Oct 4 - Oct 5
Total with taxes and fees
Bear Creek Cabin
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Exterior

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

9.8 out of 10, Exceptional, (30)
"Hindsale-perfect little hideaway, minutes from where we needed to be. Harrison’s little home was equipped with amenities/tasteful luxuries, and cozy nooks. We all loved the loft-could not believe how large the space was! Hot tub nights-perfect ending:) Thank you, Harrison."
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Exterior

Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum

9.8 out of 10, Exceptional, (57)
"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Berkshires Cabin steps from Lake
Exterior

Berkshires Cabin steps from Lake

9.6 out of 10, Exceptional, (4)
"For a winter visit, the A-frame and cedar panelling were welcoming and cozy. The 3-season room in the back would be great for a warm weather visit. Host was accessible and responsive by text. A really nice stay."
Berkshires Cabin steps from Lake
Serene Acreage - Pond - Hiking Trails Nearby
Exterior

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires
Property grounds

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires
Cozy 2-bedroom cabin in charming Becket with WiFi, AC
Exterior

Cozy 2-bedroom cabin in charming Becket with WiFi, AC

Cozy 2-bedroom cabin in charming Becket with WiFi, AC
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Everything seemed brand new. Pleasantly surprised with everything about this place. Will definitely go back!"
Lauren 1-night trip
Posted 1 day ago
Comfort Inn & Suites

Find out more about Chesterfield

Find out more about Chesterfield

Chesterfield Cabin Rentals information

Number of reviews
366
Accommodation
18 Cabin Rentals
Lowest Price
$599
Highest Price
$599

Explore a world of travel with Expedia

Explore a world of travel with Expedia