A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Pittsfield cabin rentals

A white building with a window, surrounded by trees and forest.

1. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is CA $233
CA $591 total
includes taxes & fees
Sep 15 - Sep 16
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A wooden cabin with a white door, a small porch, and a sign reading "Boulder Pines."

2. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is CA $173
CA $254 total
includes taxes & fees
Sep 15 - Sep 16
Taborton Harvest Boulder Pines Cabin in the woods
A small wooden cabin with a pitched roof, a front door, and a porch.

3. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is CA $194
CA $277 total
includes taxes & fees
Sep 15 - Sep 16
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A wooden cabin with a porch and multiple windows.

4. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (4 reviews)
"It was a great getaway "
United States
Chandra F.
The price is CA $173
CA $254 total
includes taxes & fees
Sep 15 - Sep 16
Taborton Harvest Timber Trails Unique cabin experience
A red cabin with a screened porch, a small deck, and a barbecue grill in a wooded area.

5. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is CA $277
CA $531 total
includes taxes & fees
Sep 15 - Sep 16
Ideal location for summer and winter activities with plenty of outdoor space.
A mobile home with a red awning, surrounded by a forest.

6. Luxury, modern AIRSTREAM at June Farms!

Luxury, modern AIRSTREAM at June Farms!
West Sand Lake
9.8 out of 10, Exceptional, (7 reviews)
"We’ve stayed at several of the various cabins at June Farms. This one, like the others, is unique and fantastic. Would absolutely stay again!"
United States
StephenS
The price is CA $403
CA $763 total
includes taxes & fees
Sep 15 - Sep 16
Luxury, modern AIRSTREAM at June Farms!
A log cabin with large windows and a wooden deck.

7. Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is CA $555
CA $838 total
includes taxes & fees
Sep 18 - Sep 19
Bear Creek Cabin
A small, single-story building with a sloped roof and a covered porch.

8. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
United States
KenD
The price is CA $802
CA $1,502 total
includes taxes & fees
Sep 15 - Sep 16
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
A wooden cabin with a porch, surrounded by lush greenery and trees.

9. A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (5 reviews)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
The price is CA $614
CA $1,096 total
includes taxes & fees
Sep 23 - Sep 24
A stunning, modern Lodge with rustic charm at June Farms!
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"It was perfect for our weekend away, clean, comfortable bed and a decent breakfast, definitely worth the value:)"
Kimberly 2-night trip
Posted 7 hours ago
Quality Inn Great Barrington

Find out more about Pittsfield

Pittsfield Cabin Rentals information

Number of reviews
199
Accommodation
44 Cabin Rentals
Lowest Price
CA $254
Highest Price
CA $1,502

Frequently asked questions

What are the best cabins near Pittsfield?
Ranging from small and rustic to those full of luxury and style, you have 367 cabins to pick from in and around Pittsfield. A few of the most popular options are Log Cabin Living On The Esopus Creek and Private And Artistic Cabin, Pet Friendly.
Are there cheap cabins in Pittsfield?
For a nicely priced escape in nature, look no further than our cheap cabins in Pittsfield. Wake in the morning to the sweet sound of birds chirping from one of our cozy retreats priced from CA $254 to CA $1,502 per 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 mountain cabins near Pittsfield?
If you've ever longed to sneak off to a cabin up in the mountains with only Mother Nature and amazing views for company, you're certainly not alone. The Luxury Lodge - Ski, Ride, Golf attracts plenty of guests craving time out. This mountain cabin near Pittsfield comes with many conveniences, such as nearby hunting activities and a microwave oven. Another option is Cabin - The Lakefront Retreat - Ski, Ride. A wood stove, nearby hunting activities and lots of opportunities to get out into the wilderness make it a traveller favourite.
What are the best river cabins near Pittsfield?
If you're looking for a comfy place to stay moments from the water, a Pittsfield river cabin is hard to go past. Spend your break at Cabin - Charming, Quiet, River Front and let all your troubles disappear downstream. Useful amenities here include snowsport activities and skiing facilities. Another leading riverside option is Cabin - Romantic Retreat. It features on-site watersports, snowsport activities and more.
What are the best cabins with pools near Pittsfield?
Put on your swimsuit and splash about whenever you please when you reserve one of our cabin rentals with a pool near Pittsfield. Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna ranks high among travellers. A swimming pool and a porch are some of the other amenities you can make use of here. Or you can enjoy some time out at Cabin - Romantic Retreat. Along with its pool, this cabin offers on-site watersports and a swimming pool.
Can I find beach cabins near Pittsfield?
Get your fix of sunshine and salty air at Cabin - Relax, Reconnect And Enjoy. One of our most popular Pittsfield beach cabin rentals, it features on-site watersports and children's activities. You can also spend laid-back days by the ocean at Glamping Getaway In Woodstock Lake Campground. A swimming pool and on-site watersports will help make your visit extra comfortable.
What are the best weekend cabin rentals in Pittsfield?
Nothing's as good as a weekend cabin getaway after a draining week at work. Swap the office for two or three days in the great outdoors at The Luxury Lodge - Ski, Ride, Golf. On-site watersports and a patio are some of the conveniences it offers. Alternatively, sneak in a break at Cabin - The Lakefront Retreat - Ski, Ride. Put your bags down here and make the most of on-site watersports and a patio.
What are the best cabin prices in Pittsfield?
With prices starting from as little as CA $254 per night for a cabin rental in Pittsfield, there's no reason to rough it in a tent.
Can I find log cabins in Pittsfield?
For many nature buffs, the ideal outdoor vacation just isn't complete without bunking down in a character-filled log cabin. Get your adventure on or just unplug and unwind at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Recreational activities such as shore fishing and tubing are within easy reach here. Another inviting log cabin getaway is Waterfalls - View - Pond. Secluded Log Cabin Abuts Mt Snow. Ev Outlet. Swimming and snowboarding will keep you occupied when you're not happily hibernating in your rustic retreat.
What are the highest-rated cabins in Pittsfield?
With an impressive rating, it's no surprise why Cabin - Artist's Camp On Lake Mahkeenac is a hit with Expedia vacationers. It offers useful amenities like a patio and a fireplace. Cabin With 3 Acres, Tennis Courts: By 4 Ski Mtns is another excellent choice. Conveniences such as a porch and a tennis court will help you feel right at home.
What are the top things to see and do in Pittsfield?
Spend a day or so kicking back in your charming cabin and then get exploring. Colonial Theater and Berkshire Museum are must-see's around Pittsfield. After you've crossed those off your schedule, hop behind the wheel of a rental car and visit Hancock Shaker Village and Pittsfield State Forest.
Why should I book a cabin in Pittsfield?
Affordability, comfort, rustic charm — there are lots of great reasons to choose a Pittsfield cabin. Get away from the noise of the concrete jungle and wake up to the sweet sound of birdsong. There's adventure galore just a stone's throw away too. Whether you're on vacation with family members, friends or your other half, you'll find the ideal rental cabin on Expedia.
What are the top nature cabins in Pittsfield?
The outdoors won't be the only thing you can surround yourself with when you choose a nature cabin in Pittsfield. Adventure is everywhere too. Hide away at Cabin - Charming, Quiet, River Front and go nearby snowmobiling and nearby snorkeling. Another top rental is Cabin - Romantic Retreat. It's well known for its home comforts as well as its nearby horse riding and cycling opportunities nearby.
What are some of the best cabins near Tanglewood Music Centre in Pittsfield?
Your closest neighbour is nature at a Tanglewood Music Centre cabin. Cabin - Artist's Camp On Lake Mahkeenac is one of the most popular. This escape is also big on adventure, with nearby hiking and biking trails and nearby motor boating among the activities close by. Another standout is Cozy Stockbridge Cabin - Walk To Beach And Lake. Go exploring and then return to your cabin to take advantage of its creature comforts.

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