A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Search the Best Cabins in Chester

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (171 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.
$330 nightly
The price is $370
Aug 31 - Sep 1
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

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

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (53 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
$332 nightly
The price is $356
Aug 31 - Sep 1
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

3. Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
$446 nightly
The price is $499
Sep 13 - Sep 14
Total with taxes and fees
Cozy Private Cabin in Andover - Fireplace & Hot tub
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

4. 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
$286 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
Fat Sheep Farm & Cabins
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.

5. 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, (24 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.
$482 nightly
The price is $544
Aug 31 - Sep 1
Total with taxes and fees
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$329 nightly
The price is $352
Aug 31 - Sep 1
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
A wooden interior with a dining table set for two, a sofa, and a window overlooking a forest.

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

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (19 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.
$342 nightly
The price is $367
Sep 1 - Sep 2
Total with taxes and fees
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

8. 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.
$464 nightly
The price is $556
Aug 31 - Sep 1
Total with taxes and fees
The MountainTop | Stratton & Mt Snow | Fire Pit
A cabin with a deck, surrounded by dense forest.

9. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
$468 nightly
The price is $529
Sep 2 - Sep 3
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
A wooden cabin with a metal roof, a porch, and a stack of firewood.

10. 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
Sep 13 - Sep 14
Total with taxes and fees
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
A wooden staircase leading to a cabin with a dark roof, surrounded by trees and autumn leaves.

11. A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
$634 nightly
The price is $694
Aug 31 - Sep 1
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

12. 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
$489 nightly
The price is $552
Aug 31 - Sep 1
Total with taxes and fees
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont

13. Ski-In/Ski-Out Log Cabin on Great Eastern Trail | Hot Tub, Sauna, Game Room

Ski-In/Ski-Out Log Cabin on Great Eastern Trail | Hot Tub, Sauna, Game Room
Killington
$1,199 nightly
The price is $1,355
Sep 1 - Sep 2
Total with taxes and fees
Ski-In/Ski-Out Log Cabin on Great Eastern Trail | Hot Tub, Sauna, Game Room
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

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice room and property. With was down."
Amanda 1-night trip
Posted 17 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Chester

Chester Cabin Rentals information

Number of reviews
281
Accommodation
147 Cabin Rentals
Lowest Price
$312
Highest Price
$1,355

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 $312 to $1,355 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 $312 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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