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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 33 reviews
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, 177 reviews
"This property was beautiful and literally had everything we needed to cook family meals including spices and all necessary pots/pans. I was impressed by how much this hike had available form our convenience. My only issue is that the home is advertised as a 2 bedroom but it is a loft space with 3 beds and no doors. We were not expecting this but made it work. Other than that this place is a slice of heaven!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, 141 reviews
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is ¥27,166
¥57,480 total
includes taxes & fees
Jun 25 - Jun 26
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, 19 reviews
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is ¥31,800
¥60,820 total
includes taxes & fees
Jun 28 - Jun 29
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, 116 reviews
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
9.4 out of 10, Exceptional, 10 reviews
"We loved our stay and would definitely come back."
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, 29 reviews
"Loved everything about it. Will look to book again"
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, 27 reviews
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Cabin in So. Vt enjoy the Mtns.
10.0 out of 10, Exceptional, 97 reviews
"Everything was lovely. Owners were extremely pleasant. Muffins in the morning was a great touch. We will be back."
Cabin in So. Vt enjoy the Mtns.
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, 39 reviews
"My husband and I wanted a relaxing few days to get away from our hectic lives. This small cabin was perfect, comfortable, and nicely appointed. Reading a book on the screened in porch with a cup of coffee was my favorite part. It is a quiet place in the woods but close to many small and quaint towns to visit in Vermont. The Newfane Store a few miles down the road was a great place to grab a coffee and meal. I also really appreciate that I could bring my dog. Many thanks for a warm and cozy...
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, 4 reviews
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Treehouse at Wise Pines- NoBo
10.0 out of 10, Exceptional, 4 reviews
"Tranquility at its best "
The price is ¥26,367
¥32,415 total
includes taxes & fees
Jun 25 - Jun 26
Treehouse at Wise Pines- NoBo
Award-Winning Log Cabin, Top 5 in New England!
9.8 out of 10, Exceptional, 71 reviews
"The festive decorations upon arrival were a really nice way to be greeted. We really enjoyed the fireplace insert and the plentiful supply of wood."
Award-Winning Log Cabin, Top 5 in New England!
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
9.8 out of 10, Exceptional, 100 reviews
"Property description is accurate - place was very clean. Be aware limited wi-fi and would recommmend. 4 wheel drive vehicle - would stay there again!"
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
10.0 out of 10, Exceptional, 1 review
"It was lovely the hot tub was great and loved it being right by the lake"
The price is ¥35,955
¥57,728 total
includes taxes & fees
Jul 7 - Jul 8
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
The price is ¥26,367
¥45,998 total
includes taxes & fees
Jun 30 - Jul 1
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Stunning Views in Ludlow Vermont Minutes to Okemo Resort
7.6 out of 10, Good, 4 reviews
"Once a few hiccups were worked out we had a great stay at the house in Ludlow. The previous visitors had left a large pile of trash outside and had left the hot tub cover unsecured. After we located the cover lock for the hot tub we were able to secure it so it wouldn’t keep blowing open. The silverware drawer was also broken and falling out of the cabinet. I’m sure this will be repaired. A few little problems but the house was clean and is great for a group with ability to spread out. The mud...
Stunning Views in Ludlow Vermont Minutes to Okemo Resort
Mountain View Chalet: Golf, Bike, Hike, Firepit- 7 min to MtSnow, walk to MOOver
2.0 star property
Mountain View Chalet: Golf, Bike, Hike, Firepit- 7 min to MtSnow, walk to MOOver
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, 10 reviews
"We (2) stayed in the treehouse which was perfect especially because we were just looking for the one night and most places only allow you to book 2 minimum. There were easy hiking trails directly outside of our door, along with a cute lodge/yoga studio! It was also an easy drive into Woodstock, roughly 10 minutes which was great for dinner :)"
The price is ¥26,367
¥32,575 total
includes taxes & fees
Jun 26 - Jun 27
Treehouse at Wise Pines- SoBo
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
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See all available properties in Chester
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.

Other property types in Chester

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, 32 reviews
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, 70 reviews
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is ¥54,028
¥65,373 total
includes taxes & fees
Jun 25 - Jun 26
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, 177 reviews
"This property was beautiful and literally had everything we needed to cook family meals including spices and all necessary pots/pans. I was impressed by how much this hike had available form our convenience. My only issue is that the home is advertised as a 2 bedroom but it is a loft space with 3 beds and no doors. We were not expecting this but made it work. Other than that this place is a slice of heaven!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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.

Chester Cabin Rentals information

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Frequently asked questions

What are the best cabins near Chester?
Settle into one of our 421 cabins in Chester and you’ll be rewarded with picture-perfect scenery, outdoor adventure and memories to hold on to. Cabin - Romantic Retreat: Mt. Views, Hot Tub is the place to put your bags down and your feet up. Luxury Log Cabin Lake Winnisquam Pvt Beach is another popular choice if you need time out in Mother Nature.
Are there cheap cabins in Chester?
For a nicely priced getaway in the great outdoors, look no further than our cheap cabins in Chester. Wake up in the morning to the sweet sound of birds chirping from one of our cozy cabins priced from to 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 luxury cabins near Chester?
Get set to treat yourself to a vacation that’s hard to forget at one of our Chester luxury cabins. Stunning Views In Ludlow Vermont Minutes To Okemo Resort is one option where you can spend a few days or more indulging your taste for the finer things in life. It features a spa tub and a deck. Or, use Killington Mountain Home Hottub And 5 Min To Skiing 3 Bedroom Home By Redawning as a base to explore the natural wonders around you. Quality touches here include a spa tub and fitness classes.
What are the best river cabins near Chester?
When you think of the word relaxing, a river cabin near Chester should be the first thing that enters your head. Log Cabin In The Smokeshire Valley Area Of Chester is the perfect place to find some serenity. In addition to its gorgeous surroundings, it offers amenities such as pet-friendly facilities and a firepit. New Secluded Log Cabin In The Mountains is another top choice. Nearby wildlife walks and nearby birdwatching activities are some of the conveniences you’ll have at hand here.
What are the best cabins with pools near Chester?
Slip on your swimwear and enjoy a relaxing dip whenever you want when you choose one of our cabin rentals with a pool near Chester. Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment is a winning option. On-site watersports and a swimming pool are some of the other amenities you can take advantage of here. Alternatively, spend your escape at Contemporary 4 - Bedroom Cabin 5 - Min To Okemo. As well as a pleasant pool, this cabin comes with a fireplace and a barbecue grill.
What are some great Chester cabins?
When you want to spend time with Mother Nature but don’t feel like roughing it, a cabin is the perfect solution. Stay a few nights or longer at Breathtaking Log Cabin Directly On Lake George 5bd. This traveler favorite comes with a barbecue grill, nearby museums and more. You can also experience outdoor adventure and comfort combined at Cotton Lake Cabin - Breathtaking Views Of Squam Lake And Mountain Range. A garden and a king bed are among this escape’s amenities.
What are the best weekend cabin rentals in Chester?
Whether you’re organizing a quick escape with your other half or your besties, we’ll help you find your dream weekend cabin getaway. One of our favorites? Breathtaking Log Cabin Directly On Lake George 5bd. Featuring on-site watersports and a patio, you’ll adore waking up in nature here. Cotton Lake Cabin - Breathtaking Views Of Squam Lake And Mountain Range is another terrific place where you can hit pause on life. Spend a couple of nights at this retreat which offers a patio and a fireplace.
What are the best cabin prices in Chester?
Whether you’re traveling on a shoestring or want to splash out on your next trip, you’ll find what you’re after on Expedia. At the moment, you can get a Chester cabin from as little as a night.
Can I find log cabins in Chester?
Kick off your day with a hot coffee in your homey log cabin and then while away the hours horse riding and skiing. Sound like heaven to you? Then check out Breathtaking Log Cabin Directly On Lake George 5bd. Another wooden escape that promises ample warmth and charm is Adirondack Waterfront Log Cabin. Nearby activities like picnicking and camping will add to your unforgettable experience here.
What are the highest-rated cabins in Chester?
With an impressive rating, it’s easy to understand why Breathtaking Log Cabin Directly On Lake George 5bd is so popular with Expedia vacationers. It features amenities like on-site watersports and a patio. Cotton Lake Cabin - Breathtaking Views Of Squam Lake And Mountain Range is another fabulous choice. Quality conveniences like a patio and a fireplace will help make your stay happy and comfortable.
Why should I book a cabin in Chester?
For a travel experience that’s big on charm, value for money and home comforts, a cabin is a top choice. Leave your city blues behind and wander through the greenery of nature. From days spent rambling to peaceful evenings cuddled up by a campfire, cabins offer both relaxation and excitement. Check out the terrific Chester options right here on Expedia.
What are the top nature cabins in Chester?
Featuring lots of home comforts and charm, Cabin - Beautiful Mt Area With Beautiful Scenic Views is one of our top nature cabins in Chester. But with a whole lot of things to see and do nearby, make sure you don’t spend too much time indoors. Activities such as nearby sailing and jet skiing are on the to-do list here. Cabin At Falls Romantic All Seasons Wonderland is another property where you can reconnect with nature. Nearby sailing and nearby mountain biking are a few enjoyable ways to do it.

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