Top Chester Cabin Rentals

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

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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

Grafton

Eleanor D.

CA $515 total

includes taxes & fees

Sep 30 - Oct 1

A small red cabin with a door and windows, surrounded by autumn trees and a dirt ground.

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

Cavendish

Michael L.

CA $621 total

includes taxes & fees

Oct 20 - Oct 21

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.

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

Londonderry

Meghan R.

CA $846 total

includes taxes & fees

Sep 27 - Sep 28

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

4. Fat Sheep Farm & Cabins

Windsor

Jessica

CA $400 total

includes taxes & fees

Oct 22 - Oct 23

A two-story cabin with a front porch, a covered deck, and a gravel driveway.

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

Stratton

Brenna G.

CA $806 total

includes taxes & fees

Sep 28 - Sep 29

A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

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

Cavendish

Joe C.

CA $675 total

includes taxes & fees

Sep 28 - Sep 29

A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

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

Newfane

Joseph P.

CA $417 total

includes taxes & fees

Oct 20 - Oct 21

A cabin with a deck, surrounded by dense forest.

8. Cabin on the hill Ascutney Vt - 4 bedrooms

West Windsor

Alvin

CA $698 total

includes taxes & fees

Sep 27 - Sep 28

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Top Chester Hotel Reviews

The Manchester View

10/10 Excellent

"Very cool unique setting and property. The bed was like a cloud and very relaxing."

Stone Hearth Inn and Eatery

10/10 Excellent

"Our group of four ladies had an excellent time at the historic Stone Hearth Inn. We stayed in a lovely room with 4 single beds. They were very accommodating, including a late check-in and breakfast. Breakfast included homemade bread and other fresh food in a beautiful setting overlooking the lush backyard. It is a family run operation. We were checked in and served breakfast by Vicki, because her son Edward , daughter Georgia and son-in-law Conner were all working at the local Chester Festival. We really enjoyed meeting and getting to know Vicky. We did sample fresh made donuts and pretzels at the festival. They were amazing! The room was clean and comfortable. Unfortunately, we did not get to eat in the restaurant because it was closed during the festival. We are all certain that the food there would’ve been excellent as both Georgia and Connor are master chefs. All four of us ladies highly recommend this gem in beautiful Chester, Vermont. In any season, it’s a beautiful, relaxing place to stay while exploring the things available nearby, including historic, towns and buildings, covered bridges, hiking, skiing, and great food."

Latchis Hotel

10/10 Excellent

"WE enjoyed the architecture of the whole complex - reception coffee lounge (Hot Drinks day and night as a compliment). Parking was right there. Center of town. The staff helped us when we needed to extend at the special rate. It attracts fun guests. It is a special place - not the run of the mill franchise. The linen is first class, nice thick towels. The room had a microwave and a refrig, plus the record player theme is another theme for folks who appreciate the vinyl era. Remember - Art Deco Era - not modern era."

The Jackson

8/10 Good

"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."

Find out more about Chester

Chester Cabin Rentals information

Number of reviews	394
Accommodation	147 Cabin Rentals
Lowest Price	CA $400
Highest Price	CA $1,558

Frequently asked questions

What are the best cabins near Chester?

From cute and cozy to expansive and luxurious, there are 477 cabins to pick from in and around Chester. Some great options 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 CA $400 to CA $1,558 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?

After spending your day exploring the wonders of Mother Nature, return home to the impeccable style and comfort of a Chester luxury cabin. Robert Frost Mountain Cabins is an ideal choice if you're in the mood to splash out and spoil yourself. You'll appreciate the first-rate touches here, such as pillow top mattresses and massage services. Killington Mountain Home Hottub And 5 Min To Skiing 3 Bedroom Home By Redawning is another popular stay. Make the most of a spa tub, fitness classes and a good deal more.

What are the best river cabins near Chester?

When you think of the word peaceful, a river cabin near Chester should be the first thing that enters your head. Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet is the ideal place to rediscover your Zen. As well as its gorgeous surroundings, it comes with amenities such as a wood stove and snowsport activities. Warm And Inviting Jamaica Cabin W is another top choice. A wood stove and a firepit are just some of the conveniences here.

What are the best cabins with pools near Chester?

Put on your swimwear and splash around at your leisure when you stay at one of our cabin rentals with a pool near Chester. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna is a winning option. A swimming pool and a porch are among the other amenities that await you here. Or, spend your vacation at Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet. As well as a pleasant pool, this cabin comes with a porch and a patio.

Can I find beach cabins near Chester?

Pack your favourite Hawaiian shirt and spend your seaside getaway at Cozy Private Lake Cabin Minutes To Lake George And Saratoga Springs. This Chester beach cabin rental has amenities such as on-site watersports and beach sun loungers. Cabin - Close To Skiing, Hiking, Pvt Beach also offers a sun-filled escape. Featuring on-site watersports and children's activities, it was made for easygoing days by the shore.

What are the best weekend cabin rentals in Chester?

Nothing beats a weekend cabin getaway after a hectic week at work. Swap the office cubicle for a few days in the great outdoors at Private Lake - Front Cabin With Walk. A patio and a firepit are a few of the amenities it offers. Alternatively, clear away some cobwebs at Shelving Rock Lodge On 54 Acres In Adirondack Park. Spend your nights here and make the most of 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 CA $400 a night.

Can I find log cabins in Chester?

If you pine for a simpler way of life, you'll find it at one of our log cabins in Chester. For instance, Breathtaking Log Cabin Directly On Lake George 5bd. Spend your days here boating and hiking and then return home to its many comforts. Time also seems to go slower at Lake George Custom Built Log Cabin. When you're ready to venture beyond your front yard, snowboarding and skiing opportunities are nearby.

What are the highest-rated cabins in Chester?

There are some cabins that are just about perfect. Log Cabin Retreat On 40 Acres is a great example. With an impressive rating, it comes with amenities like a patio and a fireplace. Another top option is Log Cabin Near Okemo / Ludlow On 25 Acres Borders State Forest W. A patio and a firepit are a few of the conveniences you'll find here.

Why should I book a cabin in Chester?

For a vacation in the great outdoors that won't cost a fortune, you can't go past a cabin. Imagine starting your day with the sounds of songbirds and eating breakfast on a private deck surrounded by beautiful views. Book a cabin in Chester and wave goodbye to the hectic pace of modern life. Whether they're by the beach, in the mountains or near a river, cabins offer a refreshing, rustic experience that makes them the perfect choice.

What are the top nature cabins in Chester?

Our nature cabins in Chester come in plenty of styles and budgets, but they share one thing in common — opportunities to explore the great outdoors. Warm And Inviting Jamaica Cabin W lures lots of adventure seekers. Amenities such as a fireplace and a firepit only make it more appealing. Whether you're eager to slip your feet into hiking shoes or just put them up, do it at Quiet A - Frame Cabin On Creek With Private Deck. Another great option, it comes with a porch and a firepit.

What are some of the best cabins near Okemo Mountain Resort in Chester?

You'll have Mother Nature as a neighbour at a cabin in Okemo Mountain Resort. Beautiful Cozy Log Cabin With Hot Tub is a favourite. This retreat also promises big adventure, with nearby snowboarding and nearby mountain biking among the fun things to do in the area. Also look up Summit Cabin In Ludlow 4 Bedroom Cabin By Redawning. Go exploring and then return to your cabin to make the most of its comforts.

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Treat yourself

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Check prices for these dates

Our top choices for Chester cabin rentals

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

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

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

4. Fat Sheep Farm & Cabins

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

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

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

8. Cabin on the hill Ascutney Vt - 4 bedrooms

9. The Vermont A-Frame Mountain Retreat

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

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

12. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

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

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

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

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

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Manchester View

The Equinox Golf Resort And Spa

Woodstock Inn & Resort

Pointe at Castle Hill Resort

Hampton Inn and Suites Manchester

Stone Hearth Inn and Eatery

Fullerton Inn

Latchis Hotel

The Jackson

Find out more about Chester

Chester Cabin Rentals information

Frequently asked questions

Explore a world of travel with Expedia

Find Cabins in Chester for Rent from CA $400

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester cabin rentals

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

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

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

4. Fat Sheep Farm & Cabins

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

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

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

8. Cabin on the hill Ascutney Vt - 4 bedrooms

9. The Vermont A-Frame Mountain Retreat

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

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

12. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

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

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

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

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

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Manchester View

Find out more about Chester

Chester Cabin Rentals information

Frequently asked questions

Explore a world of travel with Expedia