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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chester cabin rentals

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
$127 nightly
The price is $142
Jul 6 - Jul 7
Total with taxes and fees
The Yankee Inn
Exterior

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.8 out of 10, Good, (222 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
$103 nightly
The price is $118
Jul 6 - Jul 7
Total with taxes and fees
Baldwin Inn & Suites, SureStay Collection by Best Western
Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (179 reviews)
"It's a really nice place to stay!"
United States
Vidita
$110 nightly
The price is $122
Jul 6 - Jul 7
Total with taxes and fees
River Valley Inn
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (841 reviews)
"Plenty of parking. Staff was friendly"
United States
William
$60 nightly
The price is $67
Jul 6 - Jul 7
Total with taxes and fees
FairBridge Inn Express
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
$72 nightly
The price is $79
Jul 13 - Jul 14
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Porch

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (445 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
$118 nightly
The price is $134
Jul 6 - Jul 7
Total with taxes and fees
Naomi's Inn Bed & Breakfast
Exterior

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
$136 nightly
The price is $152
Aug 2 - Aug 3
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Front of property

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (576 reviews)
"Such a peaceful and easy stay!"
United States
Mia
$112 nightly
The price is $125
Jul 6 - Jul 7
Total with taxes and fees
The Little Lion
Exterior

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very Good, (1,004 reviews)
"Our room was very clean, staff was very friendly. We would stay here again."
United States
Sherry
$106 nightly
The price is $121
Jul 12 - Jul 13
Total with taxes and fees
Hampton Inn West Springfield
Interior

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (418 reviews)
"Nice place for a stay"
United States
Jay
$107 nightly
The price is $120
Jul 6 - Jul 7
Total with taxes and fees
Sunset Inn
Exterior

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (120 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
$166 nightly
The price is $185
Jul 12 - Jul 13
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
$149 nightly
The price is $166
Jul 7 - Jul 8
Total with taxes and fees
Berkshires Untold
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"Clean room and breakfast"
United States
Raphael
$199 nightly
The price is $222
Jul 6 - Jul 7
Total with taxes and fees
The Red Lion Inn
Front of property

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,123 reviews)
"Breakfast was excellent."
United States
Candyce
$132 nightly
The price is $147
Jul 29 - Jul 30
Total with taxes and fees
D. Hotel Suites & Spa
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (11 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
$163 nightly
The price is $182
Jul 12 - Jul 13
Total with taxes and fees
Hideaway Inn Lenox
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (878 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
$130 nightly
The price is $146
Jul 12 - Jul 13
Total with taxes and fees
Hampton Inn Westfield
Exterior

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
"It was a clean, friendly hotel."
United States
Cheri
$135 nightly
The price is $151
Jul 27 - Jul 28
Total with taxes and fees
Quality Inn Lee - Lenox South
Property grounds

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (871 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
$83 nightly
The price is $92
Jul 16 - Jul 17
Total with taxes and fees
Berkshire Inn
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,001 reviews)
"Very nice, clean, love the parking. Great hotel"
United States
Thomas Howard
$136 nightly
The price is $152
Jul 20 - Jul 21
Total with taxes and fees
The Ellery
Property entrance

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
$155 nightly
The price is $173
Aug 4 - Aug 5
Total with taxes and fees
Berkshire Mountain Lodge
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

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Great room. Staff was friendly. Very updated, newer construction. No complaints really"
Alex 3-night trip
Posted less than an hour ago
Blue – A Modern Hotel, an Ascend Collection Hotel

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
15,718
Accommodation
30 Cabin Rentals
Lowest Price
$67
Highest Price
$222

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 $67 to $222 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.
What are the best river cabins near Chester?
Spend your days making the most of the water and your nights listening to it flowing past at a river cabin near Chester. A popular option is Cabin - Charming, Quiet, River Front. This riverside property comes with snowsport activities and skiing facilities. Alternatively, unpack your bags at Cabin - Romantic Retreat. As well as its picture-perfect location, it features on-site watersports and snowsport activities.
What are the best cabins with pools near Chester?
Hop into your swimsuit and splash around whenever you want when you select one of our cabin rentals with a pool near Chester. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna is a top choice. A swimming pool and a porch are some other amenities that'll help make your stay comfortable. Or, spend your vacation at Cabin - Romantic Retreat. Along with its pool, this cabin comes with on-site watersports and a swimming pool.
Can I find beach cabins near Chester?
Pack your swimwear and get ready for a slower pace of life at Cabin - Relax, Reconnect And Enjoy. This Chester beach cabin rental comes with on-site watersports and children's activities. Lakefront - King - Petsok - W And D is another base for a sun-drenched stay. Featuring on-site watersports and clothes washing facilities, it's what beach vacation dreams are made of.
What are the best weekend cabin rentals in Chester?
Whether you're organizing a mini break with your beau or your besties, we'll help you find an amazing weekend cabin getaway. One of our top picks? This Is It Fabulous Vermont Cabin W. Featuring a patio and a firepit, you'll love being close to nature here. Cabin - Birch Hill Hollow - Mt Snow And Pool Table is another fantastic place where you can slow down for a while. Enjoy a few days or so at this retreat which offers a spa tub and a patio.
What are the best cabin prices in Chester?
Whether you're traveling on a tiny budget or want to splurge on your next vacation, you'll find what you're looking for with Expedia. At the moment, you can get a Chester cabin from just $67 a night.
Can I find log cabins in Chester?
For many nature lovers, the perfect outdoor vacation is all about staying in a log cabin. Go adventuring or simply unplug and unwind at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Activities such as cross-country skiing and shore fishing are within easy reach here. Another popular log cabin getaway is Luxury Secluded Catskill Log Cabin On Creek. Hiking and horse riding will keep you on the move when you're not resting up in your rustic digs.
What are the highest-rated cabins in Chester?
There are some places that are hard to fault. Cabin - Artist's Camp On Lake Mahkeenac is a shining example. With such an impressive rating, it comes with handy amenities such as a patio, a fireplace and loads more. Another popular option is Cabin With 3 Acres, Tennis Courts: By 4 Ski Mtns. A porch and a tennis court are just a couple of the conveniences to look forward to here.
Why should I book a cabin in Chester?
For a getaway that's big on character, value for money and home comforts, a cabin is a top choice. Leave your city blues behind and wander through the greenery of the great outdoors. From days of rugged adventure to cozy nights cuddled up by a fire, cabins offer both relaxation and excitement. Check out all the great Chester options on Expedia.
What are the top nature cabins in Chester?
The great outdoors won't be the only thing you'll be seeing plenty of when you escape to a nature cabin in Chester. Adventure is also around every corner. Get comfy at Cabin - Charming, Quiet, River Front and have a go at hiking and nearby sailing. Another option to consider is Cabin - Romantic Retreat. It's well known for its home comforts as well as its nearby hiking and biking trails and cycling opportunities nearby.
What are some of the best cabins near Holyoke Mall in Chester?
Lakefront Westhampton Cabin With Beach + Kayaks is one of the best cabins in Holyoke Mall. Ample creature comforts, a picturesque setting and activities such as nearby motor boating and nearby kayaking make it a top pick. Charming Cabin Lake Rights, Private Dock 3 Bedroom also combines nature and adventure. Get cozy here and add ice skating nearby and mountain climbing to your to-do list.

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