Search the Best Cabins in Pittsfield

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Our top choices for Pittsfield cabin rentals

Exterior
Secluded retreat in the trees

Cabin in Roxbury

Secluded retreat in the trees
10.0 out of 10, Exceptional, (38)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
$210 nightly
The price is $235
Dec 22 - Dec 23
Total with taxes and fees
Secluded retreat in the trees
Exterior
Robert Frost Mountain Cabins

Cabin in Ripton

Robert Frost Mountain Cabins
3.5 star property
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
$257 nightly
The price is $281
Jan 6 - Jan 7, 2026
Total with taxes and fees
Robert Frost Mountain Cabins
Exterior
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
$256 nightly
The price is $287
Jan 15 - Jan 16, 2026
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cabin in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
9.2 out of 10, Wonderful, (5)
$172 nightly
The price is $193
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Exterior
Stetson Hollow Cabin by Stetson Brook

Cabin in Warren

Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (159)
"Great location and a great price. Perfect for 2-4 people who just want to get away to the peace of Vermont."
United States
James N.
$390 nightly
The price is $437
Dec 23 - Dec 24
Total with taxes and fees
Stetson Hollow Cabin by Stetson Brook
Exterior
Adorable cabin with screened porch and private fire pit

Cabin in Ripton

Adorable cabin with screened porch and private fire pit
10.0 out of 10, Exceptional, (5)
"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
$317 nightly
The price is $347
Jan 6 - Jan 7, 2026
Total with taxes and fees
Adorable cabin with screened porch and private fire pit
Exterior
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cabin in Hancock

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
10.0 out of 10, Exceptional, (1)
"This place was great, and perfect for our night’s stay. The hot tub was clean and in excellent condition and we loved having that amenity! The owner was easy to get in touch with and replied to my questions very quickly. We’d love to visit again!"
United States
Stephanie F.
$355 nightly
The price is $398
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Cabin in Ripton

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
10.0 out of 10, Exceptional, (17)
"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
$321 nightly
The price is $351
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior
Cozy and pristine timberframe cabin

Cabin in Ripton

Cozy and pristine timberframe cabin
10.0 out of 10, Exceptional, (4)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
$317 nightly
The price is $347
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cozy and pristine timberframe cabin
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Cabin in Killington

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
$986 nightly
The price is $1,114
Dec 22 - Dec 23
Total with taxes and fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Exterior
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Cabin in Ripton

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
9.4 out of 10, Exceptional, (12)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
$317 nightly
The price is $347
Jan 7 - Jan 8, 2026
Total with taxes and fees
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Exterior
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

Cabin in Killington

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
10.0 out of 10, Exceptional, (1)
"Overall a great place. Beautiful location, tucked away from everything but still jist a few minutes from Killington base. Very clean and well-kept, everything we needed was there.Host communicated regularly and responded quickly.If you stay in winter, 4WD might be needed to get in and out without issue. And for the shorter route to and from Killington - its a very steep road.Beautiful interior, needs some age to feel warmer and homey, but good seating and open family room is great for...
United States
Jamie M.
$1,685 nightly
The price is $1,904
Jan 5 - Jan 6, 2026
Total with taxes and fees
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Exterior
Emrose Luxury Cabins 20

Cabin in Brandon

Emrose Luxury Cabins 20
$260 nightly
The price is $294
Dec 22 - Dec 23
Total with taxes and fees
Emrose Luxury Cabins 20
Exterior
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Cabin in Stockbridge

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
8.0 out of 10, Very Good, (1)
"Would like to have had a tv in all the bedrooms. The back yard needed mowed. Other than that it was a good stay. Nice place"
United States
Troy H.
$1,076 nightly
The price is $1,205
Dec 24 - Dec 25
Total with taxes and fees
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Exterior detail
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit

Cabin in Killington

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
2.0 star property
$1,002 nightly
The price is $1,132
Dec 23 - Dec 24
Total with taxes and fees
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
Exterior
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.

Cabin in Killington

Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
9.6 out of 10, Exceptional, (20)
"Nice place with plenty of beds, clean and comfortable!"
United States
David L.
$1,001 nightly
The price is $1,132
Dec 24 - Dec 25
Total with taxes and fees
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
Exterior
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.

Cabin in Killington

Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
10.0 out of 10, Exceptional, (13)
"Excellent location and amenities! Well stocked kitchen, plenty of towels for showering and hot tub, clean and easy access to all of Killington! "
United States
mary m.
$2,677 nightly
The price is $3,025
Dec 22 - Dec 23
Total with taxes and fees
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
Exterior
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Cabin in Ripton

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
10.0 out of 10, Exceptional, (12)
"Excellent facilities enjoyed staying there very much"
United States
Linda
$317 nightly
The price is $347
Jan 5 - Jan 6, 2026
Total with taxes and fees
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Exterior
Inviting timber frame cabin in Vermont's Green Mountains

Cabin in Ripton

Inviting timber frame cabin in Vermont's Green Mountains
10.0 out of 10, Exceptional, (6)
"This is a very special place. Close to Middleburyyetfar away. "
United States
Jim P.
$317 nightly
The price is $347
Jan 6 - Jan 7, 2026
Total with taxes and fees
Inviting timber frame cabin in Vermont's Green Mountains
Exterior
Immaculate mountain cabin with awe inspiring sunrise and mountain views

Cabin in Ripton

Immaculate mountain cabin with awe inspiring sunrise and mountain views
10.0 out of 10, Exceptional, (3)
"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.
$321 nightly
The price is $351
Jan 4 - Jan 5, 2026
Total with taxes and fees
Immaculate mountain cabin with awe inspiring sunrise and mountain views
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Friendly staff, the facility is clean and well-maintained. The room is fairly new and fully equipped. They offer free coffee, but there’s no breakfast. "
David 1-night trip
Posted 5 days ago
My Place Hotel-Randolph VT

Find out more about Pittsfield

Pittsfield Cabin Rentals information

Number of reviews
295
Accommodation
84 Cabin Rentals
Lowest Price
$193
Highest Price
$3,025

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 $193 and $3,025 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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