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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Cabin Rentals in Chester

Our top choices for 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, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (7)
"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...
$310 nightly
The price is $336
Aug 27 - Aug 28
Total with taxes and fees
Owl's Nest Treehouse
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Fridge, microwave, oven, stovetop

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
Exterior detail

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

10.0 out of 10, Exceptional, (90)
"We needed a quiet place to stay in the woods. It was close to Ludlow shops/ restaurants and the Okemo Ski. "
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore
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."
$502 nightly
The price is $567
Aug 28 - Aug 29
Total with taxes and fees
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
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!"
$301 nightly
The price is $328
Sep 8 - Sep 9
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
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, (141)
"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
Londonderry Chalet w/ Deck, Fire Pit & Views!
TV, fireplace, DVD player, books

Londonderry Chalet w/ Deck, Fire Pit & Views!

10.0 out of 10, Exceptional, (17)
"Great house with clean living space. Would recommend for any family."
Londonderry Chalet w/ Deck, Fire Pit & Views!
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (217)
"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!!
Treehouse at Wise Pines- SoBo
Property grounds

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
$188 nightly
The price is $206
Aug 25 - Aug 26
Total with taxes and fees
Treehouse at Wise Pines- SoBo
VT Cabin overlooking the West River and Village
Fridge, microwave, oven, stovetop

VT Cabin overlooking the West River and Village

9.8 out of 10, Exceptional, (34)
"We loved our stay! Such lovely cabin! We loved it so much that we were bummed we didn’t book a longer stay. It had everything we needed to make our stay comfortable."
VT Cabin overlooking the West River and Village
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Interior

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

10.0 out of 10, Exceptional, (7)
"Everything was in working order. Easy to use. Was a very tranquil stay. Will definatly be back. "
$303 nightly
The price is $330
Aug 25 - Aug 26
Total with taxes and fees
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
Property grounds

Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

9.2 out of 10, Wonderful, (19)
"The property was amazing inside and out . The view was absolutely stunning. We sat beavers eagles and different species of ducks all from the back deck ! We would absolutely stay here again!"
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
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
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, (161)
"Thank you for a peaceful weekend away in a charming cottage!"
$326 nightly
The price is $365
Aug 25 - Aug 26
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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, (7)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
$284 nightly
The price is $309
Sep 1 - Sep 2
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Trail treasures
Exterior

Trail treasures

10.0 out of 10, Exceptional, (120)
"Beautiful place."
Trail treasures
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Fridge, microwave, oven, stovetop

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

10.0 out of 10, Exceptional, (89)
"terrific time at this wonderful cabin. they had everything we needed to have fun on the lake."
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Cozy cabin in charming Londonderry
Exterior

Cozy cabin in charming Londonderry

9.0 out of 10, Wonderful, (2)
"Very cozy and quiet. "
$245 nightly
The price is $276
Aug 27 - Aug 28
Total with taxes and fees
Cozy cabin in charming Londonderry
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! "
$320 nightly
The price is $361
Aug 28 - Aug 29
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"A very nice quiet motel. The one downside was local amenities. Not much variety in restaurants and many have limited hours at this time of year."
Andrea 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort