Search Cabin Rentals in Chester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Cabin Rentals in Chester

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!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (213)
"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
Interior

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

10.0 out of 10, Exceptional, (20)
"Thanks for a great stay!"
The price is AED 643
AED 1,143 total
includes taxes & fees
11 Aug - 12 Aug
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, (158)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is AED 624
AED 1,345 total
includes taxes & fees
19 Aug - 20 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
NEW Lakeside cabin W/ Hot Tub Newly Renovated!
Outdoor spa tub

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
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior

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
Property grounds

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 AED 606
AED 759 total
includes taxes & fees
5 Aug - 6 Aug
Treehouse at Wise Pines- SoBo
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Lake

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

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 AED 1,207
AED 2,082 total
includes taxes & fees
5 Aug - 6 Aug
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
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 AED 512
AED 1,019 total
includes taxes & fees
13 Aug - 14 Aug
Cozy cabin in charming Londonderry
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, (79)
"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!
Cozy Cabin in Stratton Mountain & Mount Snow 10min
Exterior

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
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Private kitchen

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 AED 545
AED 1,326 total
includes taxes & fees
5 Aug - 6 Aug
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

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 AED 643
AED 1,111 total
includes taxes & fees
1 Sep - 2 Sep
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
The Owls Nest-A quaint cabin in the woods of VT-Near Bromley, Magic & Stratton
Exterior

The Owls Nest-A quaint cabin in the woods of VT-Near Bromley, Magic & Stratton

10.0 out of 10, Exceptional, (29)
"Great property that has met a variety of my needs. I've stayed several times; once alone, once with spouse and dog, once entertaining adult children. Communication with the host was great!"
The Owls Nest-A quaint cabin in the woods of VT-Near Bromley, Magic & Stratton
Insanely romantic treehouse perched next to a stream and rolling hills.
Fridge, microwave, oven, stovetop

Insanely romantic treehouse perched next to a stream and rolling hills.

10.0 out of 10, Exceptional, (2)
"Very nice secluded treehouse. We would definitely recommend!"
The price is AED 1,455
AED 3,233 total
includes taxes & fees
1 Sep - 2 Sep
Insanely romantic treehouse perched next to a stream and rolling hills.
Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (6)
"Treehouse was just as the pictures and description portray. It was clean, quiet and peaceful. My wife and I stayed at the Owl's Nest Treehouse for just a quick one night get away. It was the perfect spot for some quiet time alone and a soak in the hot tub. The check in process was as simple as it gets, and the owners were very responsive to the few questions we asked. For dinner we went to Springfield VT (about a 30 min drive). You can probably find something a little closer, but Alstead...
The price is AED 1,010
AED 1,239 total
includes taxes & fees
5 Aug - 6 Aug
Owl's Nest Treehouse
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Dining

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!
Sage House at Camp Greenwood Vermont with Sauna
Interior

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

10/10 Excellent
"Staff are very nice. Free breakfast appreciated!"
Danielle 1-night trip
Posted 13 hours ago
Keene Elm City Hotel, Ascend Hotel Collection