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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Cabin Rentals in Chester

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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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
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
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LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

10.0 out of 10, Exceptional, (15)
"Everything we hoped for and more. Throwback cabin, quaint, comfortable, character. "
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"This cottage never disappoints! Great place to relax, refresh and spend time with friends and family. Decor is perfect and the view and dock are off the charts. "
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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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
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (129)
"5 stars all around very relaxing and a great location. John is a great host too very accommodating!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Artist's Camp on Lake Mahkeenac
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Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (19)
"The best feature was being on the far side of Tanglewood! Getting in and out was very easy! My husband enjoyed the town beach as well"
Artist's Camp on Lake Mahkeenac
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
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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
Great Family Cabin in the woods on a lake.
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Great Family Cabin in the woods on a lake.

10.0 out of 10, Exceptional, (3)
"The cabin and lake were even better than we expected. The cabin is fully equipped with almost everything you can think of for a comfortable stay. The lake water is very clean and the surrounding forest is sustainably maintained. Doolittle Lake is a hidden gem."
Great Family Cabin in the woods on a lake.
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
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Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.8 out of 10, Exceptional, (13)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Luxe Log Cabin Minutes From Skiing, Hiking, & More
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Luxe Log Cabin Minutes From Skiing, Hiking, & More

Luxe Log Cabin Minutes From Skiing, Hiking, & More
Rustic escape on a pond with 7 acres in Colebrook, CT!
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Rustic escape on a pond with 7 acres in Colebrook, CT!

Rustic escape on a pond with 7 acres in Colebrook, CT!
Lakeshore cabin with beach and dock
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Lakeshore cabin with beach and dock

10.0 out of 10, Exceptional, (4)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with beach and dock
Berkshires Cabin steps from Lake
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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
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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
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Cozy 2-bedroom cabin in charming Becket with WiFi, AC

Cozy 2-bedroom cabin in charming Becket with WiFi, AC
Cabin in the woods w cedar Hot Tub + private pond
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Cabin in the woods w cedar Hot Tub + private pond

Cabin in the woods w cedar Hot Tub + private pond
Fantastic cottage in the Berkshire Mountains
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Fantastic cottage in the Berkshire Mountains

10.0 out of 10, Exceptional, (1)
"This cabin is very well-maintained with all the amenities you could ask for... especially no cable TV, and the owner David is responsive and pleasant! It is the perfect place to unplug, unwind and reconnect with life, nature and whoever you're traveling with. The house is an easy 30 minutes to Tanglewood and 20 minutes to Great Barrington so there is plenty to see and do without feeling like always being in the car. We got takeout from a delicious Thai restaurant (Siam Square) in Great...
Fantastic cottage in the Berkshire Mountains
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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Top Chester Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"All that was needed is a Hot tub for these elderly bones and raise the temperature in the pool "
Frederick 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA