Find Cabins in Chester for Rent from CA $192

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Chester Cabin Rentals

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (45)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (212)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (18)
"Thanks for a great stay!"
The price is CA $242
CA $431 total
includes taxes & fees
Aug 11 - Aug 12
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is CA $235
CA $507 total
includes taxes & fees
Aug 19 - Aug 20
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
NEW Lakeside cabin W/ Hot Tub Newly Renovated!
Exterior

NEW Lakeside cabin W/ Hot Tub Newly Renovated!

NEW Lakeside cabin W/ Hot Tub Newly Renovated!
Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs OK
Exterior

Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs OK

10.0 out of 10, Exceptional, (1)
"Had a great couple days at the "glamping cabin." The ride to get there on a dark foggy night was a bit thrilling, but could immediately relax once I got into the cabin. Place has everything needed for a semi-primitive cabin experience. Enjoyed the sauna and thencozy bed. "
Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs OK
Treehouse at Wise Pines- NoBo
Exterior

Treehouse at Wise Pines- NoBo

9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
The price is CA $227
CA $285 total
includes taxes & fees
Aug 4 - Aug 5
Treehouse at Wise Pines- NoBo
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (53)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Treehouse at Wise Pines- SoBo
Exterior

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is CA $227
CA $285 total
includes taxes & fees
Aug 4 - Aug 5
Treehouse at Wise Pines- SoBo
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Exterior

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay."
The price is CA $452
CA $781 total
includes taxes & fees
Aug 4 - Aug 5
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
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Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (138)
"Cute cabin close to Okemo and town! Really enjoyed our stay and would definitely return. "
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
The price is CA $246
CA $432 total
includes taxes & fees
Aug 3 - Aug 4
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Exterior

Beautiful country cabin with hot tub and outdoor shower in Londonderry

2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
The price is CA $205
CA $497 total
includes taxes & fees
Aug 5 - Aug 6
Beautiful country cabin with hot tub and outdoor shower in Londonderry
The Owls Nest-A quaint cabin in the woods of VT-Near Bromley, Magic & Stratton
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The Owls Nest-A quaint cabin in the woods of VT-Near Bromley, Magic & Stratton

10.0 out of 10, Exceptional, (29)
"The cabin is in a beautiful location. It filled up my soul and I would DEFINITELY book this wonderful place again!"
The Owls Nest-A quaint cabin in the woods of VT-Near Bromley, Magic & Stratton
Cozy Cabin in Stratton Mountain & Mount Snow 10min
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Cozy Cabin in Stratton Mountain & Mount Snow 10min

10.0 out of 10, Exceptional, (5)
"The place was very clean & a good location. The host was friendly & responsive."
Cozy Cabin in Stratton Mountain & Mount Snow 10min
Cozy cabin in charming Londonderry
Exterior

Cozy cabin in charming Londonderry

9.0 out of 10, Wonderful, (2)
"Very cozy and quiet. "
The price is CA $192
CA $382 total
includes taxes & fees
Aug 19 - Aug 20
Cozy cabin in charming Londonderry
Owl's Nest Treehouse
Exterior

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (6)
"My husband and I had a great weekend at Owl's Nest. The space was small, but cozy and the space was so well thought out in every way. It was meticulously clean, the lighting was magical, the hot tub was so cozy, and the host was very thoughtful in providing k-cups and local syrup and honey! Even though the cabin is on the same property as another house, it felt secluded. If you stay at this cabin, I definitely recommend going to L.A. Burdick in Walpole and having dinner at Wunderbar in Bellows...
The price is CA $379
CA $465 total
includes taxes & fees
Aug 5 - Aug 6
Owl's Nest Treehouse
Award-Winning Log Cabin, Top 5 in New England!
Exterior

Award-Winning Log Cabin, Top 5 in New England!

9.8 out of 10, Exceptional, (78)
"Our trip was nothing short of perfect! The cabin is gorgeous! Everything you need is there or nearby. We will definitely return."
Award-Winning Log Cabin, Top 5 in New England!
Sage House at Camp Greenwood Vermont with Sauna
Exterior detail

Sage House at Camp Greenwood Vermont with Sauna

10.0 out of 10, Exceptional, (3)
"I had a great stay, kitchen is fully equipped. The place is clean and cozy. My dtay was very relaxing. Would definitely stay again."
Sage House at Camp Greenwood Vermont with Sauna
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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Charming Wilmington Cabin, 8 Mi. to Mt Snow!

9.8 out of 10, Exceptional, (40)
"Awesome setup and location. Hosts were absolutely fantastic - would stay again :)"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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 Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"All good "
richard 1-night trip
Posted 18 hours ago
The Covered Bridge Inn