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

Search the Best Cabins in Pittsfield

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In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Pittsfield cabin rentals

Exterior

1. 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
9.6 out of 10, Exceptional, (21 reviews)
"Cozy, classic, basic, old school Killington condo. Loved the wood stove. Easy access to Killington area. "
United States
Leslie P.
$466 nightly
The price is $527
Sep 10 - Sep 11
Total with taxes and fees
Cabin at Killington Left: 4BR with Wood Stove, Deck and Hot Tub
Exterior

2. 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.
$470 nightly
The price is $531
Sep 10 - Sep 11
Total with taxes and fees
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Exterior

3. Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway

Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Mendon
$486 nightly
The price is $549
Sep 13 - Sep 14
Total with taxes and fees
Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Exterior

4. 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.
$514 nightly
The price is $575
Sep 10 - Sep 11
Total with taxes and fees
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior

5. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (15 reviews)
"That was the most beautiful stay that we’ve had in a long time. Everything was absolutely perfect. We will definitely be back."
United States
Kaity F.
$300 nightly
The price is $336
Sep 20 - Sep 21
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior

6. Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (46 reviews)
"Very cozy and easy check in!"
United States
Emily R.
$240 nightly
The price is $269
Sep 21 - Sep 22
Total with taxes and fees
Secluded retreat in the trees
Exterior

7. Brookside Cabin - Your Peaceful VT Off-Grid Escape

Brookside Cabin - Your Peaceful VT Off-Grid Escape
Brookfield
$396 nightly
The price is $444
Sep 10 - Sep 11
Total with taxes and fees
Brookside Cabin - Your Peaceful VT Off-Grid Escape
Exterior

8. Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (175 reviews)
"Jill was very attentive to make sure we had everything we needed very nice stay!"
United States
Kathy B.
$401 nightly
The price is $449
Sep 10 - Sep 11
Total with taxes and fees
Stetson Hollow Cabin by Stetson Brook
Exterior

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.
$390 nightly
The price is $437
Sep 16 - Sep 17
Total with taxes and fees
Charming TREEHOUSE in remote location
Exterior

10. 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.
$1,189 nightly
The price is $1,344
Sep 10 - Sep 11
Total with taxes and fees
Entire Killington Cabin Duplex: 8BR, Two Kitchens and Hot Tub
Cabin 6 (Pet Free) - Evening Star | Pillowtop beds, iron/ironing board, travel crib, WiFi (free)

11. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place great owner"
United States
Joe
$330 nightly
The price is $359
Sep 17 - Sep 18
Total with taxes and fees
Robert Frost Mountain Cabins
Exterior

12. 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.
$1,228 nightly
The price is $1,388
Sep 13 - Sep 14
Total with taxes and fees
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Property grounds

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
$344 nightly
The price is $376
Sep 10 - Sep 11
Total with taxes and fees
Adorable cabin with screened porch and private fire pit
Exterior

14. 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
$396 nightly
The price is $433
Sep 16 - Sep 17
Total with taxes and fees
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior

15. 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
$367 nightly
The price is $402
Sep 13 - Sep 14
Total with taxes and fees
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Exterior

16. 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.
$393 nightly
The price is $430
Sep 14 - Sep 15
Total with taxes and fees
Cozy and pristine timberframe cabin
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.
$344 nightly
The price is $376
Sep 10 - Sep 11
Total with taxes and fees
Immaculate mountain cabin with awe inspiring sunrise and mountain views
Exterior

18. 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.
$368 nightly
The price is $403
Sep 17 - Sep 18
Total with taxes and fees
Inviting timber frame cabin in Vermont's Green Mountains
Exterior

19. 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
$420 nightly
The price is $459
Oct 1 - Oct 2
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

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"A++ will be back soon"
Charlie 1-night trip
Posted 3 hours ago
Emrose Luxury Cabins

Find out more about Pittsfield

Pittsfield Cabin Rentals information

Number of reviews
385
Accommodation
69 Cabin Rentals
Lowest Price
$269
Highest Price
$1,388

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 $269 and $1,388 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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