Find Cabins in Chesterfield for Rent from CA $365

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Chesterfield Cabin Rentals

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Outdoor dining

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

10.0 out of 10, Exceptional, (34)
"We loved the “cabin in the sky”! It was as cozy as being at home. Super clean and comfortable. We absolutely loved it! "
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Owl's Nest Treehouse
Outdoor dining

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (1)
"My husband and I had a great weekend at Owl's Nest. The space was small, but cozy and the space was so well thought out in every way. It was meticulously clean, the lighting was magical, the hot tub was so cozy, and the host was very thoughtful in providing k-cups and local syrup and honey! Even though the cabin is on the same property as another house, it felt secluded. If you stay at this cabin, I definitely recommend going to L.A. Burdick in Walpole and having dinner at Wunderbar in Bellows...
The price is CA $379
CA $464 total
includes taxes & fees
May 5 - May 6
Owl's Nest Treehouse
Jacksonville Cabin w/ Wraparound Deck & Views
Interior

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (29)
"Perfect cabin with beautiful views."
Jacksonville Cabin w/ Wraparound Deck & Views
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
TV, fireplace, DVD player, books

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (117)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (11)
"The host was amazing. Very kind and very responsive! Made great suggestions for places to eat. The property is quiet and great for relaxation! 10/10 will stay agin! "
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Cozy Log Cabin on the River | Fireplace | Loft
3 bedrooms, desk, WiFi, bed sheets

Cozy Log Cabin on the River | Fireplace | Loft

10.0 out of 10, Exceptional, (11)
"It was clean and a nice place."
Cozy Log Cabin on the River | Fireplace | Loft
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.6 out of 10, Exceptional, (23)
"Very nice, clean, and great area. We enjoyed it very much!"
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
Fridge, microwave, stovetop, dishwasher

Cozy Mount Snow Chalet w/ Game Room & Hot Tub

10.0 out of 10, Exceptional, (11)
"Great place for a weekend with friends and family. "
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
Cozy Cabin Retreat on Putney Mountain
Fridge, microwave, oven, stovetop

Cozy Cabin Retreat on Putney Mountain

10.0 out of 10, Exceptional, (2)
"This cabin is so cozy and clean, had plenty of room for 4 guests, the wood burning stove and sauna were great amenities to have for a winter trip. The house has all the little things that you may have forgotten to bring such as towels, coffee, cleaning supplies, etc. Will definitely remember this stay while planning future trips! Just remember to take a vehicle that can handle Vermont snow!"
Cozy Cabin Retreat on Putney Mountain
Hike & Swim On-Site: Cozy Falls Brook Cabin
Fridge, microwave, stovetop, coffee/tea maker

Hike & Swim On-Site: Cozy Falls Brook Cabin

10.0 out of 10, Exceptional, (10)
"Great little cabin, would definitely stay again!"
Hike & Swim On-Site: Cozy Falls Brook Cabin
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (51)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (36)
"We had a wonderful stay! Perfect for two people !"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Alpine A-Frame - midcentury cabin by Lake Raponda
Outdoor dining

Alpine A-Frame - midcentury cabin by Lake Raponda

2.0 out of 10, (1)
Alpine A-Frame - midcentury cabin by Lake Raponda
Cozy Log Cabin - Dog Friendly
Exterior

Cozy Log Cabin - Dog Friendly

9.8 out of 10, Exceptional, (10)
"It was so peaceful and restful, we didn't even want to go anywhere else and do anything, but stay at the cabin and relax."
Cozy Log Cabin - Dog Friendly
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow
Video games, DVD player, table tennis, books

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

10.0 out of 10, Exceptional, (12)
"Great house for groups or a big family. Lots of games/arcade/ping pong. Hot tub jazuzzi tub in the master bedroom were so nice to have.It was an investment, but was worth it to be able to have the whole family comfortably. "
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow
Classic, dog-friendly cabin in the woods w/ private deck
3 bedrooms, internet, bed sheets

Classic, dog-friendly cabin in the woods w/ private deck

9.0 out of 10, Wonderful, (58)
"Great stay. Nicer than the pictures"
Classic, dog-friendly cabin in the woods w/ private deck
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Property grounds

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

10.0 out of 10, Exceptional, (14)
"We had a fantastic stay! The house was clean, comfortable and close to several ski resorts. All the amenities were perfect and met all of our needs. It is beautiful spot to get away!"
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Cabin Retreat in Southern Vermont
Property grounds

Cabin Retreat in Southern Vermont

8.4 out of 10, Very good, (6)
"Loved the hot tub!"
Cabin Retreat in Southern Vermont
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

9.8 out of 10, Exceptional, (39)
"Perfect cabin if you're looking to decompress and disconnect from every day hectic life. Cute cozy romantic little cabin, owner was on top with communication and accommodations overall an amazing experience."
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Aerial view

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

10.0 out of 10, Exceptional, (2)
"It was a sweet and cozy little cottage. Absolutely perfect. Clean, safe and so close to the mountain!! Would absolutely love to stay here again!"
The price is CA $365
CA $711 total
includes taxes & fees
May 11 - May 12
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
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 Chesterfield

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a large house with so many areas for activities. Close to a lot of fun things to do like axe throwing, an escape room, distilleries, breweries, etc."
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (50)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (47)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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.

Frequently asked questions

What are the best cabins near Chesterfield?
Get cozy at one of our 314 cabins in Chesterfield and you’ll be rewarded with stunning scenery, outdoor adventure and great memories. Cabin - Private Retreat With Breathtaking River Views is the place to go for an unplugged getaway. Private And Artistic Cabin, Pet Friendly is another popular option if you’d love some time out in nature.
Are there cheap cabins in Chesterfield?
Whether you’d like to stay by the water or on the top of a mountain, we’ve got a great variety of cheap cabins in Chesterfield to suit your taste and budget. Priced from CA $365 to CA $379 a night, your perfect cabin rental is waiting right here.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 Chesterfield?
Splash out and enjoy a getaway you won’t forget at one of our Chesterfield luxury cabins. Killington Mountain Home Hottub And 5 Min To Skiing 3 Bedroom Home By Redawning is one option where you can spend a couple of days indulging your love of the finer things in life. It features a spa tub and fitness classes. Alternatively, use Stunning Views In Ludlow Vermont Minutes To Okemo Resort as a base to explore the beautiful natural areas around you. Amenities here include a king-sized bed and a deck.