Find Cabins in Pittsfield for Rent from CA $179

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Pittsfield Cabin Rentals

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (219)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Bear Creek Cabin
Exterior

Bear Creek Cabin

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
The price is CA $552
CA $826 total
includes taxes & fees
Aug 24 - Aug 25
Bear Creek Cabin
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Exterior

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (124)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Newly Renovated Cabin in the Country
Exterior

Newly Renovated Cabin in the Country

10.0 out of 10, Exceptional, (30)
"Very comfortable place with everything we needed for great week!"
Newly Renovated Cabin in the Country
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is CA $179
CA $262 total
includes taxes & fees
Aug 20 - Aug 21
Taborton Harvest Boulder Pines Cabin in the woods
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA
Outdoor dining

Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA

10.0 out of 10, Exceptional, (1)
"The cabin is charming, rustic, and a perfect getaway for a birthday or romantic weekend trip.The pollinator garden is truly a delight, and I loved watching them in the morning. The garden has even motivated my partner and I to start one at home.I wish that the mosquitoes were not present as well, but they are to be expected during the summer in MA.Overall, the stay was amazing. Marci was super sweet and left some nice gifts for my birthday. I definitely want to have another stay here again!"
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA
Florida Mountain Log Cabin!
TV

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Place was super clean. Beds were comfortable. Location was great."
The price is CA $282
CA $582 total
includes taxes & fees
Sep 3 - Sep 4
Florida Mountain Log Cabin!
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
1 bedroom, in-room safe, WiFi, bed sheets

Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

10.0 out of 10, Exceptional, (14)
"Unfortunately, we were not there for a whole lot of daylight because this location is extremely beautiful."
The price is CA $279
CA $430 total
includes taxes & fees
Sep 1 - Sep 2
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

9.8 out of 10, Exceptional, (30)
"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Artist's Camp on Lake Mahkeenac
Sun loungers, beach towels

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (19)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Dadzpad Cabin in Stephentown
Fridge, microwave, oven, stovetop

Dadzpad Cabin in Stephentown

5.0 out of 10, (2)
"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "
Dadzpad Cabin in Stephentown
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Exterior

Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum

9.8 out of 10, Exceptional, (57)
"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Ideal location for summer and winter activities with plenty of outdoor space.
Terrace/patio

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

9.8 out of 10, Exceptional, (72)
"Excellent host!"
Ideal location for summer and winter activities with plenty of outdoor space.
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is CA $179
CA $260 total
includes taxes & fees
Aug 20 - Aug 21
Taborton Harvest Timber Trails Unique cabin experience
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (44)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
The price is CA $215
CA $437 total
includes taxes & fees
Sep 2 - Sep 3
Charming 3-bedroom Cabin for nature lovers
Berkshires Cabin 2 Mi to Appalachian Trail!
Dining

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (12)
"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "
Berkshires Cabin 2 Mi to Appalachian Trail!
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Interior

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.8 out of 10, Exceptional, (13)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Private Hot Tub: Hudson Valley Cabin Retreat!
Dining

Private Hot Tub: Hudson Valley Cabin Retreat!

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had an excellent stay, went skiing at Butternut, tubing at Bousquet, and celebrated New Years at the house. Tons for the kids to do, well stocked kitchen (no condiments tho so bring your own ketchup, etc). Home owner was very responsive. Would definitely book again. "
Private Hot Tub: Hudson Valley Cabin Retreat!
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.6 out of 10, Excellent, (8)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
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.
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Enjoyed the room, towels and kitchen. I can recommend. "
daniel 3-night trip
Posted 20 hours ago
Berkshire Mountain Lodge