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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester cabin rentals

A red house with a covered porch and a chimney.

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (173 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
$331 nightly
The price is $371
Oct 19 - Oct 20
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

2. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
$178 nightly
The price is $194
Nov 2 - Nov 3
Total with taxes and fees
Fat Sheep Farm & Cabins
A rustic cabin with a wooden exterior, a metal roof, and a small porch with railings.

3. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
$244 nightly
The price is $275
Oct 19 - Oct 20
Total with taxes and fees
Cozy cabin in charming Londonderry
A blue single-story house with a red roof, a front door, and two windows.

4. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow
8.0 out of 10, Very good, (3 reviews)
"Great location and very cozy cottage. Well-appointed place to stay and accurately described in its listing. "
United States
jeremy a.
$315 nightly
The price is $356
Oct 18 - Oct 19
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

5. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (55 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
$377 nightly
The price is $406
Nov 9 - Nov 10
Total with taxes and fees
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A snow-covered building with a sloped roof, large arched windows, and a door.

6. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
$325 nightly
The price is $367
Oct 26 - Oct 27
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
A small red cabin with a door and windows, surrounded by autumn trees and a dirt ground.

7. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$378 nightly
The price is $407
Nov 11 - Nov 12
Total with taxes and fees
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

8. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
$254 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A small red cabin with a door and windows, surrounded by autumn trees and a dirt ground.

9. Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards

Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
$377 nightly
The price is $406
Nov 9 - Nov 10
Total with taxes and fees
Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
Bridge | Foot Traffic Only, No Driving

10. Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (21 reviews)
"it is beautiful quiet location.. love the bridge and creek on the property."
United States
Krisann B.
Hiking Trails On-Site: Cozy Falls Brook Cabin
A rustic cabin with a stone foundation, a sloped roof, and a chimney. It features a porch with steps leading to the entrance, and a small attached shed.

11. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (25 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
$651 nightly
The price is $735
Nov 16 - Nov 17
Total with taxes and fees
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A cabin with a sloped roof, surrounded by snow-covered trees, and illuminated by string lights.

12. Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont

Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
Jamaica
$1,081 nightly
The price is $1,222
Nov 3 - Nov 4
Total with taxes and fees
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
A wooden cabin with a metal roof, a porch, and a stack of firewood.

13. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (11 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
$749 nightly
The price is $846
Oct 19 - Oct 20
Total with taxes and fees
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A cabin with a deck, surrounded by dense forest.

14. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
$486 nightly
The price is $549
Oct 18 - Oct 19
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
A snow-covered path leading to a building with a lit entrance, surrounded by trees.

15. Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna

Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna
Londonderry
2.0 out of 10, (1 review)
"their was no AC it was over 100 degrees "
United States
Anthony R.
$586 nightly
The price is $663
Oct 20 - Oct 21
Total with taxes and fees
Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna
A wooden cabin with a balcony, surrounded by lush greenery and a stone pathway.

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

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Londonderry
8.0 out of 10, Very good, (12 reviews)
"We had a wonderful stay."
United States
Joshua
$502 nightly
The price is $567
Oct 19 - Oct 20
Total with taxes and fees
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
A rustic building with a wooden deck, string lights, and a window overlooking a garden.

17. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (7 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$232 nightly
The price is $260
Nov 2 - Nov 3
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A two-story cabin with a front porch, a covered deck, and a gravel driveway.

18. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
$420 nightly
The price is $475
Oct 21 - Oct 22
Total with taxes and fees
The MountainTop | Stratton & Mt Snow | Fire Pit
A log cabin with a wooden door and windows, surrounded by snow.

19. Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont

Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
Winhall
10.0 out of 10, Exceptional, (1 review)
$506 nightly
The price is $572
Oct 19 - Oct 20
Total with taxes and fees
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
A wooden cabin with a porch, surrounded by trees and a stone wall.

20. Brookside Cabin + Hot Tub | Woodstock & Killington

Brookside Cabin + Hot Tub | Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (9 reviews)
"Highly recommend, the house was not only aesthetically appealing, but very well stocked for our needs and more, owners are super attentive and just overall 5 stars without question. "
United States
Amber F.
$807 nightly
The price is $880
Nov 7 - Nov 8
Total with taxes and fees
Brookside Cabin + Hot Tub | Woodstock & Killington
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"Ij kii it"
Kevin 2-night trip
Posted 8 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
374
Accommodation
151 Cabin Rentals
Lowest Price
$194
Highest Price
$1,222

Frequently asked questions

What are the best cabins near Chester?
From cute and cozy to big and luxurious, there are 475 cabins on offer in and around Chester. Standouts include Cabin - Romantic Retreat: Mt. Views, Hot Tub and Cabin - Close To Skiing, Hiking, Pvt Beach.
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 $194 to $1,222 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?
Our Chester luxury cabins offer style and comfort while staying in the great outdoors. You'll appreciate the high-end amenities at Robert Frost Mountain Cabins. Pillow top mattresses and massage services help make this getaway a favorite. Alternatively, relax in luxury at Killington Mountain Home Hottub And 5 Min To Skiing 3 Bedroom Home By Redawning, which comes with 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 come to mind. Warm And Inviting Jamaica Cabin W is the perfect place to find some stillness. In addition to its pretty surroundings, it offers amenities such as a wood stove and a firepit. Quiet A - Frame Cabin On Creek With Private Deck is another enticing option. A firepit and a queen bed are just some of the conveniences that await you here.
What are the best cabins with pools near Chester?
Staying in a cabin rental with a pool adds another level of fun to your vacation. If you're chasing one near Chester, Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna offers amenities like a swimming pool and a porch to make your poolside escape even more perfect. Log Cabin - Cozy, Quaint And Scenic And Ready For Your Enjoyment is another top choice and features on-site watersports and a swimming pool.
Can I find beach cabins near Chester?
Pack your board shorts and soak up the seaside vibes at Cozy Private Lake Cabin Minutes To Lake George And Saratoga Springs. This Chester beach cabin has amenities including on-site watersports and beach sun loungers. Cabin - Close To Skiing, Hiking, Pvt Beach also delivers a sun-drenched stay. Featuring on-site watersports and children's activities, it's what beach vacation dreams are made of.
What are the best weekend cabin rentals in Chester?
Whether you're organizing a short break with your honey or your besties, we'll help you locate the perfect weekend cabin getaway. One awesome option? Private Lake - Front Cabin With Walk. Featuring a patio and a firepit, you'll love the natural setting here. Shelving Rock Lodge On 54 Acres In Adirondack Park is another fantastic place where you can hit pause. Enjoy a few nights at this escape which offers on-site watersports and a patio.
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 $194 a night.
Can I find log cabins in Chester?
If you're pining for a slower pace of life, you'll find it at one of our log cabins in Chester. For example, Cabin - Close To Skiing, Hiking, Pvt Beach. Spend your days here going hiking and snowboarding and then return home to its rustic charms. Time also seems to slow down at Breathtaking Log Cabin Directly On Lake George 5bd. When you want to venture beyond your front step, camping and skiing opportunities are close by.
What are the highest-rated cabins in Chester?
With an impressive rating, it's not surprising why Log Cabin Retreat On 40 Acres is such a favorite with Expedia travelers. It offers useful amenities like a patio and a fireplace. Log Cabin Near Okemo / Ludlow On 25 Acres Borders State Forest W is another great choice. Conveniences such as a patio and a firepit will help you feel right at home.
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?
Our nature cabins in Chester come in many budgets and styles, but there's one feature they all share — access to the great outdoors. Warm And Inviting Jamaica Cabin W is a magnet for nature buffs. Amenities such as a firepit and a barbecue grill make it even more inviting. Whether you'd rather slip your feet into hiking boots or simply put them up, you can do it at Quiet A - Frame Cabin On Creek With Private Deck. Another favorite, it offers a barbecue grill and a firepit.
What are some of the best cabins near Weston Playhouse in Chester?
The Owls Nest - A Quaint Cabin In The Woods Of Vt is one of the best cabins in Weston Playhouse. Plenty of comforts, beautiful surroundings and activities such as nearby mountain biking and nearby cross-country skiing help make it the perfect escape. New Secluded Log Cabin In The Mountains is another place where nature and adventure go hand in hand. Spend your break here and add nearby sledding and mountain climbing to your to-do list.

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