Find Cabins in Old Chatham for Rent from CA $165

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Old Chatham Cabin Rentals

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, (122)
"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 $165
CA $244 total
includes taxes & fees
Aug 9 - Aug 10
Taborton Harvest Boulder Pines Cabin in the woods
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)
"Lovely location, charming property, great experience"
The price is CA $272
CA $427 total
includes taxes & fees
Aug 12 - Aug 13
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
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
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.
"Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"
Smart TV, fireplace, video games, books

"Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"

10.0 out of 10, Exceptional, (6)
"Had a great time at this property - would stay again!"
The price is CA $775
CA $1,418 total
includes taxes & fees
Aug 19 - Aug 20
"Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"
Luxurious & Modern 3 BR 1.5 Bath Log Cabin
Dining

Luxurious & Modern 3 BR 1.5 Bath Log Cabin

9.6 out of 10, Exceptional, (4)
"Spotlessly clean cabin beautifully decorated with a modern cabin vibe. 20 minutes from Great Barrington & Butternut ski area. 10 minutes to Catamount ski area. Would definitely rent again."
Luxurious & Modern 3 BR 1.5 Bath Log Cabin
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 $165
CA $244 total
includes taxes & fees
Aug 9 - Aug 10
Taborton Harvest Timber Trails Unique cabin experience
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 $275
CA $520 total
includes taxes & fees
Aug 29 - Aug 30
Charming 3-bedroom Cabin for nature lovers
The Collar City Oasis |Pet Friendly|Workspace|Laundry|Hospitals & Colleges|WIFI
Fridge, microwave, oven, stovetop

The Collar City Oasis |Pet Friendly|Workspace|Laundry|Hospitals & Colleges|WIFI

9.6 out of 10, Exceptional, (9)
"Lots of room, good location, great host."
The Collar City Oasis |Pet Friendly|Workspace|Laundry|Hospitals & Colleges|WIFI
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!
Crooked Lake Cabin
Smart TV

Crooked Lake Cabin

10.0 out of 10, Exceptional, (3)
"Very quiet very neat cottage on a small lake in Albany areaI would highly recommend this property.Lake view is beautiful with lots of windows to watch the water and boats working kitchen has new appliances, bathroom totally updated washer and dryer a big plus as well We felt relaxedas soon as we walked in"
Crooked Lake Cabin
Cozy Stockbridge Cabin - Walk to Beach & Lake!
TV

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (11)
"Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm"
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Beautiful cabin in the woods close to skiing, hiking and shopping
Smart TV, fireplace, video games, foosball

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

Beautiful cabin in the woods close to skiing, hiking and shopping
Pet-Friendly Cabin Overlooking Sleepy Hollow Lake
Fridge, microwave, stovetop, dishwasher

Pet-Friendly Cabin Overlooking Sleepy Hollow Lake

9.6 out of 10, Exceptional, (80)
"Had a great experience staying at this house - owner was responsive and the views were amazing."
Pet-Friendly Cabin Overlooking Sleepy Hollow Lake
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
3 bedrooms, iron/ironing board, free WiFi, bed sheets

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

10.0 out of 10, Exceptional, (2)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Gather Greene
Comfort Cabin, 1 King Bed, Mountainside

Gather Greene

3.0 star property
10.0 out of 10, Exceptional, (3)
"serenity at its finest very peaceful"
Gather Greene
Martin Van Buren historical Log cabin
Private kitchen

Martin Van Buren historical Log cabin

2.0 star property
Martin Van Buren historical Log cabin
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 Old Chatham Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."
Susan 1-night trip
Posted 17 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG