Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AU$347
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AU$833
includes taxes & fees
2 Dec - 3 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (20)
"clean, wonderful views of the lake. "
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

10.0 out of 10, Exceptional, (3)
"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"
Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (33)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Great location and beautifully appointed house. Cindy is very helpful and responsive."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AU$574
includes taxes & fees
2 Dec - 3 Dec
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

2 bedroom town house with game room

6.4 out of 10, (13)
"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."
The price is AU$272
includes taxes & fees
2 Dec - 3 Dec
2 bedroom town house with game room

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (15)
"Amanda is a very responsive and accommodating host. The house was comfortable and perfect for our girls weekend with plenty of space for us to relax and feel at home. "
The price is AU$491
includes taxes & fees
9 Dec - 10 Dec
Near Tanglewood: Historic Summer Retreat

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Modern Glass House designed by renowned architect Thomas Phifer

8.8 out of 10, Excellent, (3)
"For those of us who live in big Cities. This is truly a rare find! It’s so different and so unique! We were thrilled with the view and massive outdoor space. We love it so much! We will keep this house when we are in the area in the future! "
Modern Glass House designed by renowned architect Thomas Phifer
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 Chatham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"Staff was very professional and polite "
The price is AU$300
includes taxes & fees
2 Dec - 3 Dec
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AU$318
includes taxes & fees
2 Dec - 3 Dec
Jiminy Peak Mountain Resort

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.