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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
The price is CA $181
CA $202 total
includes taxes & fees
Jul 6 - Jul 7
The Yankee 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
The price is CA $84
CA $94 total
includes taxes & fees
Jul 6 - Jul 7
FairBridge Inn Express
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
The price is CA $147
CA $168 total
includes taxes & fees
Jul 8 - Jul 9
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
The price is CA $148
CA $165 total
includes taxes & fees
Jul 6 - Jul 7
River Valley Inn
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
The price is CA $113
CA $126 total
includes taxes & fees
Jul 6 - Jul 7
Berkshire Inn
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
The price is CA $152
CA $170 total
includes taxes & fees
Jul 7 - Jul 8
Sunset Inn
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
The price is CA $168
CA $190 total
includes taxes & fees
Jul 7 - Jul 8
Naomi's Inn Bed & Breakfast
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
The price is CA $105
CA $115 total
includes taxes & fees
Jul 7 - Jul 8
Pleasant Valley Motel West Stockbridge
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
The price is CA $193
CA $216 total
includes taxes & fees
Aug 2 - Aug 3
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
The price is CA $159
CA $178 total
includes taxes & fees
Jul 7 - Jul 8
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
The price is CA $150
CA $172 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn West Springfield
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
The price is CA $235
CA $263 total
includes taxes & fees
Jul 12 - Jul 13
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
The price is CA $237
CA $265 total
includes taxes & fees
Jul 7 - Jul 8
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
The price is CA $251
CA $344 total
includes taxes & fees
Jul 22 - Jul 23
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
The price is CA $173
CA $202 total
includes taxes & fees
Jul 27 - Jul 28
D. Hotel Suites & Spa
Exterior

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield
2.5 star property
West Springfield
7.0 out of 10, Good, (1,004 reviews)
"Love the stay"
United States
Jake
The price is CA $133
CA $152 total
includes taxes & fees
Jul 19 - Jul 20
Red Roof Inn PLUS+ West Springfield
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
The price is CA $208
CA $232 total
includes taxes & fees
Jul 6 - Jul 7
Hideaway Inn Lenox
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (877 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is CA $185
CA $207 total
includes taxes & fees
Jul 12 - Jul 13
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
The price is CA $192
CA $214 total
includes taxes & fees
Jul 29 - Jul 30
Quality Inn Lee - Lenox South
Front of property

Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,004 reviews)
"Great location and I had a room with a private deck."
United States
Jonathan
The price is CA $211
CA $236 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Northampton
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Great service and friendly staff "
Ly 1-night trip
Posted 4 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
15,709
Accommodation
18 Cabin Rentals
Lowest Price
CA $94
Highest Price
CA $344

Frequently asked questions

What are the best cabins near Chester?
Discover the great outdoors without surrendering the comforts at one of our 275 cabins in and around Chester. Whether you have relaxation or adventure on your to-do list, Log Cabin Living On The Esopus Creek delivers plenty of both. Alternatively, spend your break at Sfa Lodge Log Cabin 4 Bd - 2 Ba Nestled In The Woods 5 Mins From Berkshire East and enjoy staring out at its wonderful natural surroundings.
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 CA $94 to CA $344 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?
Bunk down in a mountain cabin near Chester and experience dramatic views, outdoor activities and memories you won't forget. Cabin - Charming, Quiet, River Front is a tough act to beat. Tucked high in the hills, you'll find useful amenities like snowsport activities and skiing facilities here. This Is It Fabulous Vermont Cabin W is another popular option. It comes with a wood stove, winery tours and scenery to make you swoon.
What are the best river cabins near Chester?
If you're looking for a comfortable place to stay overlooking the water, a Chester river cabin is hard to beat. Head for Cabin - Charming, Quiet, River Front and let any bothers scurry away downstream. Useful amenities here include snowsport activities and skiing facilities. Another popular riverside getaway is Cabin - Romantic Retreat. Guests have use of on-site watersports, snowsport activities and more.
What are the best cabins with pools near Chester?
Staying in a cabin rental with a pool adds a level of fun to your vacation. If you're seeking one near Chester, Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna offers conveniences like a swimming pool and a porch to make your poolside escape even more awesome. Cabin - Romantic Retreat is another favourite with travellers and features on-site watersports and a swimming pool.
Can I find beach cabins near Chester?
Get your hit of salty air and sunshine at Cabin - Relax, Reconnect And Enjoy. One of our best Chester beach cabins, it offers on-site watersports and children's activities. You can also spend lazy days by the ocean at Cabin - Lakefront - King - Petsok - W And D. On-site watersports and clothes washing facilities will help make your time here extra comfortable.
What are the best weekend cabin rentals in Chester?
Nothing's better than a weekend cabin getaway after a big week at work. Swap the office cubicle for a few days in nature at Cabin - Charming, Quiet, River Front. A patio and a firepit are a few of the amenities it offers. Otherwise, forget all about work at This Is It Fabulous Vermont Cabin W. Settle in here and take advantage of a patio and a firepit.
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 CA $94 a night.
Can I find log cabins in Chester?
For lots of nature lovers, the perfect outdoor vacation isn't complete without bunking down in a log cabin full of charm and character. Get adventurous or simply unplug and unwind at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Recreational activities such as fishing and cycling are among the exciting things to do here. Another enticing log cabin getaway is Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet. Cross-country skiing and tubing will keep you on the move when you're not kicking back in your rustic hideaway.
What are the highest-rated cabins in Chester?
Vacationers can't get enough of Cabin - Artist's Camp On Lake Mahkeenac. This superb option comes with lots of handy amenities like a patio and a fireplace. It's easy to understand why Cabin With 3 Acres, Tennis Courts: By 4 Ski Mtns is also popular with visitors. Conveniences such as a porch and a tennis court will help make your stay even more memorable.
Why should I book a cabin in Chester?
For a vacation in nature at an amazing price, there's nothing better than a cabin. Visualize yourself waking up to the sounds of the wilderness and then wandering onto your deck to be surrounded by stunning views. Lock in a cabin in Chester and wave goodbye to the hectic pace of modern life. Whether they're beachside, lakeside or up a mountain, cabins offer a rustic and relaxing experience you won't forget.
What are the top nature cabins in Chester?
The outdoors won't be the only thing you'll be experiencing plenty of while vacationing in a nature cabin in Chester. Adventure is at every turn too. Get cozy at Cabin - Charming, Quiet, River Front and make time for some nearby scuba diving and hiking. Another standout is Cabin - Romantic Retreat. It's renowned for its creature comforts on top of its nearby horse riding and nearby hiking and biking trails opportunities nearby.
What are some of the best cabins near International Volleyball Hall of Fame in Chester?
Ditch the daily grind and step out into nature from an International Volleyball Hall of Fame cabin. Stroll among the wildlife, take in the fresh air and then put your feet up at Lakefront Westhampton Cabin With Beach + Kayaks. Awesome activities such as nearby motor boating and nearby kayaking are waiting for you here. Another place you'll love coming home to is Charming Cabin Lake Rights, Private Dock 3 Bedroom. Mountain climbing and a bicycle are a couple of things to add to your itinerary during your trip.

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