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Search the Best Cabins in Chester

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Aug 22 - Aug 24

Cabin Rentals in Chester

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Exterior

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (119)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (41)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Interior

Lakefront Westhampton Cabin w/ Beach + Kayaks!

10.0 out of 10, Exceptional, (8)
"Loved our stay. "
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Berkshires Cabin 2 Mi to Appalachian Trail!
Dining

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "
Berkshires Cabin 2 Mi to Appalachian Trail!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

10.0 out of 10, Exceptional, (24)
"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!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Artist's Camp on Lake Mahkeenac
Property grounds

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (18)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Terrace/patio

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

9.6 out of 10, Exceptional, (59)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Tolland Cabin w/ Private Hot Tub & Grill!
Fridge, microwave, stovetop, dishwasher

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (13)
"OVERALL GREAT TIME WAS HAD !!!! AAA +++"
Tolland Cabin w/ Private Hot Tub & Grill!
'The Mill River Cabin’ w/ Fireplace & River View!
Dining

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (38)
"We had a great time during our stay at the Mill Creek cabin! The views of the river couldn't be beat & we enjoyed spending time reading on the porch & watching the wildlife from the huge living room windows. We will definitely be back!"
'The Mill River Cabin’ w/ Fireplace & River View!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
TV

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (8)
"Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm"
Cozy Stockbridge Cabin - Walk to Beach & Lake!
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Property grounds

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.8 out of 10, Exceptional, (7)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
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, (216)
"The house was small, cozy and even had a small stream that ran through the backyard and under the deck. It had everything we needed. A bigger TV in the living room but definitely be a big upgrade but that isn't the end of the world. Would stay here again. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
2 bedrooms, iron/ironing board, internet, bed sheets

Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

9.0 out of 10, Wonderful, (30)
"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!"
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Interior

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.8 out of 10, Exceptional, (12)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
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
Great Family Cabin in the woods on a lake.
Interior

Great Family Cabin in the woods on a lake.

10.0 out of 10, Exceptional, (2)
"We love this place as the lake is extremely quiet and clean. The house has a great living room with lots of charm and plenty of bathroom and bedroom space. I wish I had something bad to say because we could keep it to ourselves, but I do not."
Great Family Cabin in the woods on a lake.
Rustic escape on a pond with 7 acres in Colebrook, CT!
2 bedrooms, free WiFi, bed sheets

Rustic escape on a pond with 7 acres in Colebrook, CT!

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

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Luxe Log Cabin Minutes From Skiing, Hiking, & More
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
TV, fireplace, DVD player

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

8.4 out of 10, Very Good, (8)
"Lovely cottage. Very clean. Everything we needed. We had a great time!"
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (7)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
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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Frequently asked questions

What are the best cabins near Chester?
Ranging from small and basic to large and luxurious, you have 273 cabins to select from in and around Chester. Some great options include Log Cabin Living On The Esopus Creek and Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East.
Are there cheap cabins in Chester?
For an affordable vacation in nature, have a look at our cheap cabins in Chester. Wake each morning to the sound of birds twittering from one of our cozy cabins priced from to a night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best mountain cabins near Chester?
If you're after fresh air and gorgeous views, head for the hills and stay in a Chester mountain cabin. Get your head in the clouds at Cabin - Charming, Quiet, River Front. This guest favorite has all you need for an enjoyable getaway, such as snowsport activities and skiing facilities. Alternatively, experience a taste of the mountain lifestyle at This Is It Fabulous Vermont Cabin W. It features a wood stove, winery tours and more.