A lake surrounded by autumn-colored trees and a rocky shoreline.

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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 Pittsfield cabin rentals

A rustic cabin with a metal roof, surrounded by dense forest.

1. Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Stockbridge
9.0 out of 10, Wonderful, (2 reviews)
"The host was very responsive! The house was very clean when we came and had everything we needed."
United States
Angela W.
$953 nightly
The price is $1,067
Oct 18 - Oct 19
Total with taxes and fees
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
A wooden building with a white door, a bear sculpture with a sign, and a window with a view of trees and mountains.

2. Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
Killington
6.0 out of 10, (2 reviews)
"A beautiful, and very well-maintained property. We booked it specifically for the hot tub and fire pit combo and it did not disappoint! We were also pleasantly surprised to find plenty of dry firewood stacked and ready to go for us to use upon our arrival. I'd recommend this place to anyone wanting to get away for the weekend at any time of the year!"
United States
Justin A.
$661 nightly
The price is $747
Oct 18 - Oct 19
Total with taxes and fees
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
A two-story house with a snow-covered roof and a wooden deck.

3. Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub

Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub
Killington
10.0 out of 10, Exceptional, (18 reviews)
"great stay!"
United States
Patrick M.
$1,130 nightly
The price is $1,277
Oct 19 - Oct 20
Total with taxes and fees
Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub
A wooden cabin with a snow-covered roof, surrounded by a snowy forest at dusk.

4. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (43 reviews)
"Very nice place great owner"
United States
Joe
$352 nightly
The price is $384
Oct 22 - Oct 23
Total with taxes and fees
Robert Frost Mountain Cabins
A house with a sloped roof, a front porch, and a well-maintained lawn.

5. Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington
9.8 out of 10, Exceptional, (65 reviews)
"Amazing location, cozy cabin with plenty of beds for sleeping , owners were super responsive will def love to stay again!"
United States
Robert D.
$492 nightly
The price is $556
Oct 19 - Oct 20
Total with taxes and fees
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
A two-story house with a snow-covered roof and a wooden deck.

6. Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub

Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub
Killington
9.4 out of 10, Exceptional, (22 reviews)
"Cozy, classic, basic, old school Killington condo. Loved the wood stove. Easy access to Killington area. "
United States
Leslie P.
$523 nightly
The price is $591
Oct 18 - Oct 19
Total with taxes and fees
Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub
A rustic wooden cabin with a porch, surrounded by autumn foliage.

7. NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (4 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
$1,114 nightly
The price is $1,259
Nov 15 - Nov 16
Total with taxes and fees
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
A gravel driveway leading to a rustic barn and a stone house surrounded by lush greenery.

8. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
$437 nightly
The price is $490
Oct 22 - Oct 23
Total with taxes and fees
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
A treehouse with a wooden exterior and a snow-covered roof, situated in a snowy forest.

9. Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location
Braintree
10.0 out of 10, Exceptional, (2 reviews)
"Views amazing and so cool"
United States
Benjamin F.
$286 nightly
The price is $321
Oct 27 - Oct 28
Total with taxes and fees
Charming TREEHOUSE in remote location
A log cabin with a green door, two windows, and a porch.

10. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
9.4 out of 10, Exceptional, (13 reviews)
"It is a beautiful location in a fully equipped cabin off the beaten path."
United States
Steven
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A house surrounded by trees with a snow-covered ground and a stream.

11. Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (51 reviews)
"Such a peaceful place to stay, we absolutely loved it there"
United States
Katherine
$226 nightly
The price is $253
Oct 21 - Oct 22
Total with taxes and fees
Secluded retreat in the trees
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

12. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A hand holding a leaf with a cabin in the background.

13. Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
$322 nightly
The price is $352
Nov 8 - Nov 9
Total with taxes and fees
Adorable cabin with screened porch and private fire pit
A rustic cabin surrounded by dense forest.

14. Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (182 reviews)
"Jill was very attentive to make sure we had everything we needed very nice stay!"
United States
Kathy B.
$405 nightly
The price is $454
Oct 19 - Oct 20
Total with taxes and fees
Stetson Hollow Cabin by Stetson Brook
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

15. Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin
Ripton
10.0 out of 10, Exceptional, (4 reviews)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
Cozy and pristine timberframe cabin
A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

16. Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains
Ripton
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, charming, and very clean cabin with excellent communication with team and fun access to trails, hot tub and game room."
United States
Kelly I.
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
Inviting timber frame cabin in Vermont's Green Mountains
Exterior

17. Immaculate mountain cabin with awe inspiring sunrise and mountain views

Immaculate mountain cabin with awe inspiring sunrise and mountain views
Ripton
10.0 out of 10, Exceptional, (3 reviews)
"Our cabin was lovely—artfully built, well-stocked, perfectly clean, and very comfortable. We awoke to silence and a beautiful view of the mountains from our screened porch. We are already planning our return!"
United States
Sara S.
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
Immaculate mountain cabin with awe inspiring sunrise and mountain views
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

18. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Ripton
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
$319 nightly
The price is $349
Nov 5 - Nov 6
Total with taxes and fees
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
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 Pittsfield Hotel Reviews

The Shire Woodstock

The Shire Woodstock

8/10 Good
"Few amenities but nice view of river and clean. No one at front desk before 8am for check out. Overall, we enjoyed our stay."
Gregory 2-night trip
Posted less than an hour ago
The Shire Woodstock

Find out more about Pittsfield

Pittsfield Cabin Rentals information

Number of reviews
408
Accommodation
69 Cabin Rentals
Lowest Price
$253
Highest Price
$1,277

Frequently asked questions

What are the best cabins near Pittsfield?
Stay in one of our 669 cabins in Pittsfield and be rewarded with striking scenery, outdoor fun and memories to treasure. Cabin - Romantic Retreat: Mt. Views, Hot Tub is the place to go for a relaxing getaway. A Great 4 Season Home Relaxing is another popular option if you could do with some time out in Mother Nature.
Are there cheap cabins in Pittsfield?
Priced between $253 and $1,277 per night, escaping the everyday has never been easier. Lock in one of our cheap cabins in Pittsfield and enjoy an adventure-filled vacation without blowing your budget.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 Pittsfield?
After spending your day exploring nature, head home to the high-end comforts of a Pittsfield luxury cabin. Robert Frost Mountain Cabins is an excellent option if you'd love to splash out and spoil yourself. You'll enjoy the premium touches here, such as pillow top mattresses and massage services. Cabin - Pollard Brook Condo In Great Lincoln is another enticing stay. Make the most of a swimming pool, a spa tub and a whole lot more.
What are the best river cabins near Pittsfield?
Spend your days having fun near the water and your nights listening to it surging past at a river cabin near Pittsfield. A popular choice is Log Cabin On The Hudson. This riverside stay offers snowsport activities and outdoor furniture. Or, spend your vacation at Warm And Inviting Jamaica Cabin W. Along with its gorgeous location, highlights here include a wood stove and a firepit.
What are the best cabins with pools near Pittsfield?
Staying in a cabin rental with a pool adds a whole new layer of fun to your vacation. If you're chasing one near Pittsfield, 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 awesome. Welcome To Northaven Family - Friendly Lakefront Cabin In The White Mountains is another great pick and features on-site watersports and a swimming pool.
Can I find beach cabins near Pittsfield?
Enjoy sunset strolls along the shoreline when you reserve a Pittsfield beach cabin rental. Sunshine and good times should be your biggest priorities at Cozy Private Lake Cabin Minutes To Lake George And Saratoga Springs. This seaside stay comes with on-site watersports and beach sun loungers. Alternatively, throw your bag down and make yourself at home at Log Cabin On The Hudson. Handy amenities here include clothes washing facilities and children's activities.
What are the best weekend cabin rentals in Pittsfield?
Whether you're organizing a whirlwind break with your honey or your besties, we'll help you locate the perfect weekend cabin getaway. One top example? Cabin - High Peaks Mountain Retreat. Featuring on-site watersports and a porch, you'll love the natural surroundings here. Private Lake - Front Cabin With Walk is another terrific place where you can hit pause. Enjoy a few days or so at this retreat which offers a patio and a firepit.
Can I find log cabins in Pittsfield?
For lots of nature lovers, the perfect outdoor vacation just isn't complete without bunking down in a charming log cabin. Get out and explore or simply relax and unwind at Log Cabin On The Hudson. Activities such as snowboarding and boating are among the exciting things to do here. Another attractive log cabin getaway is Authentic Log Cabin - Mountain Views. Snow shoeing and camping will keep you occupied when you're not unwinding in your rustic abode.
What are the highest-rated cabins in Pittsfield?
Expedia cabin travelers just keep going back to Private Lake - Front Cabin With Walk. This hot spot features a host of amenities like a patio and a firepit. It's not hard to work out why Classic Green Mountain Cabin is also a hit with vacationers. Conveniences such as a barbecue grill and nearby museums will help make your stay even more enjoyable.
Why should I book a cabin in Pittsfield?
Affordability, outdoor attractions, rustic charm — there are loads of good reasons to book a Pittsfield cabin. Escape the clamor of the concrete jungle and wake up to the sounds of birds and wildlife. There's a whole lot of adventure just beyond your door too. Whether you're vacationing with family, friends or your honey, you'll find the perfect cabin on Expedia.
What are the top nature cabins in Pittsfield?
Our nature cabins in Pittsfield come in numerous styles and shapes, but there's one thing they have in common — superb access to the great outdoors. Log Cabin On The Hudson lures vacationers chasing adventure. Amenities such as a firepit and a patio add to its appeal. Whether you'd rather wriggle your feet into hiking boots or simply put them up, do it at Warm And Inviting Jamaica Cabin W. Another favorite, it offers a firepit and a fireplace.
What are some of the best cabins near Killington Peak in Pittsfield?
Ditch the daily grind and spend time with Mother Nature at a Killington Peak cabin. Stroll among the wildlife, get some fresh air and then settle in at Cabin - Ski On/off Spruce Glen 4 Acre Retreat On Great Eastern Trail. Popular activities such as skiing and nearby hiking and biking trails are outside your door here. Another place you'll enjoy coming home to is Ski In And Out Spruce Glen Townhomes On Great Eastern Trail. Downhill skiing and ski runs are a couple of things to put on your itinerary during your break.

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