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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun
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, (213)
"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
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, (40)
"We had a great time here and the hosts were friendly and accommodating of our request for a later checkout. Our only complaint is the 325 cleaning fee, which is excessive given how much cleaning guests are asked to do (and given that one of the bathrooms was not even perfectly clean upon arrival). We would otherwise happily consider a future stay."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (29)
"Enjoyed our stay"
The price is HK$3,103
HK$4,636 total
includes taxes & fees
26 Apr - 27 Apr
Bear Creek Cabin
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Aerial view

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

9.8 out of 10, Exceptional, (11)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is HK$1,086
HK$2,325 total
includes taxes & fees
28 Apr - 29 Apr
Charming 3-bedroom Cabin for nature lovers
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

10.0 out of 10, Exceptional, (24)
"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
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.

9.6 out of 10, Exceptional, (70)
"As is our custom we picked a place to celebrate Thanksgiving with our family. The location is usually in an area that is quiet, out in the country. This property did not disappoint us. Vivianna is a great host, always answering any questions or concerns. Great location, tucked away off the road, but close to all things one may need. Great fireplace, cozy living room dining area and bedrooms. We would recommend this property to anyone who is looking for a place to just relax and enjoy the...
Ideal location for summer and winter activities with plenty of outdoor space.
Martin Van Buren historical Log cabin
Private kitchen

Martin Van Buren historical Log cabin

2.0 star property
Martin Van Buren historical Log cabin
Cabin in the woods
Exterior

Cabin in the woods

10.0 out of 10, Exceptional, (10)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is HK$931
HK$1,378 total
includes taxes & fees
26 Apr - 27 Apr
Cabin in the woods
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
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, (8)
"Kelly was a great host. Looking to come back in the summer for sure!"
The price is HK$1,280
HK$2,084 total
includes taxes & fees
30 Apr - 1 May
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Florida Mountain Log Cabin!
Living area

Florida Mountain Log Cabin!

2.0 star property
The price is HK$3,065
HK$5,060 total
includes taxes & fees
29 Apr - 30 Apr
Florida Mountain Log Cabin!
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very good, (7)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
A-Frame Cabin w/ Furnished Deck in Becket!
Beautiful cabin in the woods close to skiing, hiking and shopping
Smart TV, fireplace, video games, table football

Beautiful cabin in the woods close to skiing, hiking and shopping

Beautiful cabin in the woods close to skiing, hiking and shopping
Taborton Harvest Timber Trails Unique cabin experience
Exterior

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 HK$931
HK$1,378 total
includes taxes & fees
29 Apr - 30 Apr
Taborton Harvest Timber Trails Unique cabin experience
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)
"A group of 10 friends (we are in out 40's) and I stayed here for a yearly gathering that we do. Every person was amazed at the rental. It was warm, clean, inviting and the kitchen jad everything that i needed to feed 10 people over the weekend.The game room was amazing and kept the group active indoors. It had a beautiful fireplace and wood stove. The adjacent room had a dining table, another wood stove and some very thoughtful items in a welcome basket. Next to that was the kitchen/living...
Private Hot Tub: Hudson Valley Cabin Retreat!
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!
Exterior

TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!

9.8 out of 10, Exceptional, (6)
"June Farms is a great place to unplug and recharge. The people there are wonderful!!!!!! We can’t wait to go back!!!!!"
The price is HK$1,047
HK$1,859 total
includes taxes & fees
30 Apr - 1 May
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!
Artist's Camp on Lake Mahkeenac
Property map

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (18)
"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

8.0 out of 10, Very good, (1)
"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
Modern Cabin Near Tanglewood
Property grounds

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (8)
"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "
Modern Cabin Near Tanglewood
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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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is HK$4,259
HK$8,029 total
includes taxes & fees
28 Apr - 29 Apr
Hancock Village Inn at Jiminy Peak
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"This is a great little house in Pittsfield. Location was perfect for us, as it's just a couple of miles from our son's apartment. It's a beautiful farm, tucked away on a back road. It seems "rural" when you're at the house, but it's actually right near everything you could possibly need. The owners were great with communication and very accommodating. We hope to be back, and it's great to know that the house has enough room for our other kids to join if they want to. "
Dancing Horse Lodge
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.

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 cosy retreats priced from HK$931 to HK$3,103 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.