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

Search the Best Cabins in Pittsfield

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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 detail

1. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (17 reviews)
"This was a dash away and perfect! "
United States
Linda R.
$165 nightly
The price is $183
Sep 9 - Sep 10
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

2. 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.
$412 nightly
The price is $460
Sep 10 - Sep 11
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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
$181 nightly
The price is $201
Sep 9 - Sep 10
Total with taxes and fees
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Exterior

4. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (3 reviews)
"It was a great getaway "
United States
Chandra F.
$165 nightly
The price is $183
Sep 9 - Sep 10
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Exterior

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
$339 nightly
The price is $380
Sep 9 - Sep 10
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
Exterior

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
$492 nightly
The price is $546
Sep 14 - Sep 15
Total with taxes and fees
Luxury, modern AIRSTREAM at June Farms!
Exterior

7. Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
$539 nightly
The price is $602
Sep 13 - Sep 14
Total with taxes and fees
Bear Creek Cabin
Exterior

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
$1,049 nightly
The price is $1,164
Sep 15 - Sep 16
Total with taxes and fees
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Exterior

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
$712 nightly
The price is $790
Sep 23 - Sep 24
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great location, fair price, clean and spacious"
Steven 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Cabin Rentals information

Number of reviews
201
Accommodation
44 Cabin Rentals
Lowest Price
$183
Highest Price
$1,164

Frequently asked questions

What are the best cabins near Pittsfield?
Immerse yourself in the outdoors without having to rough it at one of our 363 cabins in and around Pittsfield. Whether you have relaxation or fun on your itinerary, Log Cabin Living On The Esopus Creek promises both. Alternatively, get comfy at Private And Artistic Cabin, Pet Friendly and enjoy staring out at its beautiful natural surroundings.
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 $183 to $1,164 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 yearned to sneak off to a cabin in the mountains with only nature and epic views for company, you're certainly not alone. Cabin - Hunter Lakefront House: Ski, Swim attracts plenty of adventurers. This mountain cabin near Pittsfield comes with home comforts, such as a microwave oven and a dishwasher. Another standout is Cabin - Charming, Quiet, River Front. Snowsport activities, skiing facilities and plenty of opportunities to explore the outdoors help make it a crowd-pleaser.
What are the best river cabins near Pittsfield?
If you're looking for a relaxing getaway surrounded by water, a Pittsfield river cabin is the perfect choice. Kick back at Cabin - Charming, Quiet, River Front and let any stresses disappear downstream. Handy amenities here include snowsport activities and skiing facilities. Another superb riverside stay is Cabin - Romantic Retreat. You'll have use of on-site watersports, snowsport activities and more.
What are the best cabins with pools near Pittsfield?
Staying in a cabin rental with a pool adds another level of excitement 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 memorable. Cabin - Romantic Retreat is another top pick and features on-site watersports and a swimming pool.
Can I find beach cabins near Pittsfield?
Wake up and be within easy reach of glittering blue waters when you lock in a stay at a Pittsfield beach cabin rental. Sun and fun should be your major priorities at Cabin - Relax, Reconnect And Enjoy. This seaside retreat offers on-site watersports and children's activities. Or, throw your beach bag down and spend a few nights at Glamping Getaway In Woodstock Lake Campground. Conveniences here include a swimming pool and on-site watersports.
What are the best weekend cabin rentals in Pittsfield?
Whether you're organizing a short trip with your beau or your whole family, we'll help you locate the perfect weekend cabin getaway. One superb example? This Is It Fabulous Vermont Cabin W. Featuring a patio and a firepit, you'll appreciate being close to nature here. Cabin - Birch Hill Hollow - Mt Snow And Pool Table is another terrific place where you can hit pause. Enjoy a few nights or more at this escape which offers a spa tub and a patio.
What are the best cabin prices in Pittsfield?
With prices starting from as little as $183 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 some, the perfect outdoor vacation isn't complete without staying in a log cabin. Get out and active or simply switch off and unwind at Charming Traditional Log Cabin In Between Mt. Snow And Stratton With Sauna. Activities such as cross-country skiing and tubing are close at hand here. Another attractive log cabin getaway is Luxury Secluded Catskill Log Cabin On Creek. Mountain climbing and horse riding will keep you entertained when you're not unwinding in your comfy hideaway.
What are the highest-rated cabins in Pittsfield?
With an impressive rating, it's not hard to see why Cabin - Artist's Camp On Lake Mahkeenac is recommended by Expedia adventurers. Some useful amenities here include a patio and a fireplace. Cabin With 3 Acres, Tennis Courts: By 4 Ski Mtns is another fabulous choice. Conveniences such as a porch and a tennis court will help make your stay a comfy one.
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?
For a vacation in nature that won't cost a fortune, you can't top a cabin. Picture yourself waking up to the sounds of wildlife and then stepping onto your deck to be surrounded by dreamy views. Book a cabin in Pittsfield and say goodbye to the busyness of the city. Whether they're by the beach, in the mountains or near a river, cabins offer a refreshing, rustic experience you'll always remember.
What are the top nature cabins in Pittsfield?
Featuring plenty of home comforts and charm, Cabin - Charming, Quiet, River Front is among our most sought-after nature cabins in Pittsfield. But with so many things to do and see nearby, you won't want to spend too much time indoors. Activities including nearby water skiing and nearby rafting are waiting. Cabin - Romantic Retreat is another place where you can hang out in nature. Golf and nearby basketball are a couple of enjoyable ways to do it.
What are some of the best cabins near National Shrine of the Divine Mercy in Pittsfield?
Mother Nature is your neighbor at a cabin in National Shrine of the Divine Mercy. Cozy Stockbridge Cabin - Walk To Beach And Lake is a popular choice. This getaway is also big on adventure, with nearby hiking and biking trails and nearby motor boating among the activities in the area. Also check out Cabin - Artist's Camp On Lake Mahkeenac. Get active and then head back to your cabin to enjoy its comforts.

Explore a world of travel with Expedia