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Compare 92 Cabin Rentals in Chester with updated reviews, rates, and availability.

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

9.4 out of 10, Exceptional, (36)
"This property was just what we were looking for in a weekend getaway in VT. Would highly recommend. "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (148)
"The area was amazing and the views were incredible. "
The price is AED 624
AED 1,353 total
includes taxes & fees
25 Nov - 26 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Cozy cabin near skiing with free WiFi, game room, deck, & wood fireplace

9.0 out of 10, Wonderful, (105)
"We stayed in the property for 2 nights. It was a short drive from okemo ski resort. The home is clean and lots of entertainment. Kitchen is pretty well equipped. The home is on top of a steep driveway so make sure you have 4WD if you go in the winter. Only complaint is that the didn’t have any firewood in the house for the fireplace. We did ended up getting some on our own and I’m still waiting for them to reimburse me."
Cozy cabin near skiing with free WiFi, game room, deck, & wood fireplace

New Renovated Ski Chalet on the River with a Hottub

10.0 out of 10, Exceptional, (2)
"Conor was very easy to get in touch with. The location of the place was ideal!"
New Renovated Ski Chalet on the River with a Hottub

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

9.0 out of 10, Wonderful, (17)
"Leaves, cheese and syrup! Wonderful view on the lake! We appreciated the use of the kayaks and canoe!"
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

10.0 out of 10, Exceptional, (12)
"Love this property. We had everything we needed and then some. wasn't exactly sure as to where to put the trash as I don't have email on my phone , therefore I didn't receive the email about the trash and laundry until I got back home. I would rather have been able to text but everything worked out for us, and we had a wonderful, relaxing time."
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Cozy Falls Brook Cabin: Hike & Swim On-Site!

10.0 out of 10, Exceptional, (9)
"The cabin is immaculate and very cute and cozy. It's lovely to be right by the brook in a quiet neighborhood set in a woodsy area. Lots of great places a short right away too. Brattleboro is lots of fun, and we loved hiking in the Manitou Project."
Cozy Falls Brook Cabin: Hike & Swim On-Site!

Brand New Luxury “Tiny” House, Immersed In Nature

10.0 out of 10, Exceptional, (1)
"This is by far the most beautiful home I’ve ever stayed! So clean and amazing views of nature. We can’t wait to come back."
The price is AED 1,010
AED 1,633 total
includes taxes & fees
23 Nov - 24 Nov
Brand New Luxury “Tiny” House, Immersed In Nature

Contemporary 4-BR Cabin 5-min to Okemo

Contemporary 4-BR Cabin 5-min to Okemo

Mt. Snow/Stratton Log Cabin in the Woods

9.8 out of 10, Exceptional, (18)
"We were there for a Family reunion in a nearby town. Perfect spot for us. Place was beautiful and everything we needed. Would be a great spot for a ski vacation. Mt. Snow was close and some great food nearby. Bob was great with communication. "
Mt. Snow/Stratton Log Cabin in the Woods

Andover Cabin Retreat w/ Hot Tub & Fireplace!

10.0 out of 10, Exceptional, (2)
"The cabin was just what we were looking for. A Thanksgiving weekend for 2 , secluded, quiet and romantic with the hot tub and woodburning stove"
Andover Cabin Retreat w/ Hot Tub & Fireplace!

Londonderry Chalet w/ Deck, Fire Pit & Views!

10.0 out of 10, Exceptional, (15)
"Very quiet and relaxing"
Londonderry Chalet w/ Deck, Fire Pit & Views!

Log Cabin Minutes from Jackson Gore and Okemo Mountain!!!!!!!

10.0 out of 10, Exceptional, (10)
"This house was perfect for our needs during our ski trip to Vermont."
Log Cabin Minutes from Jackson Gore and Okemo Mountain!!!!!!!

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"This place was basically brand new and spotless. Hiking, kayaking and hot tub right outside your door. Close enough to civilization, if you want it. Would like to go there again. Highly recommend it."
The price is AED 643
AED 1,124 total
includes taxes & fees
3 Dec - 4 Dec
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cozy 2-bedroom cabin near Mount Snow 3 min drive

2.0 star property
10.0 out of 10, Exceptional, (1)
"I really enjoyed every aspect of my stay here and highly recommend the property. "
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (19)
"Beautiful property and wonderful host. Very welcoming and cozy, and within a quick drive of lots of great activities. I would definitely stay here again!"
The price is AED 533
AED 654 total
includes taxes & fees
24 Nov - 25 Nov
Treehouse at Wise Pines- SoBo

VT Cabin overlooking the West River and Village

10.0 out of 10, Exceptional, (27)
"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."
The price is AED 459
AED 1,092 total
includes taxes & fees
23 Nov - 24 Nov
VT Cabin overlooking the West River and Village

Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt

10.0 out of 10, Exceptional, (125)
"Very clean and well stocked with all needs."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
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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Other property types in Chester

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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.