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Compare 448 Vacation Homes in Chatham with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is SAR 563
SAR 855 total
includes taxes & fees
20 Feb - 21 Feb
Berkshire Village Carriage House - Super Private!!

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"Stayed at the house over Christmas with family. The house is well-appointed with excellent heat. Hosts were excellent at communicating with us when we had questions."
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

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.

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (37)
"The house was great. Plenty of bedrooms to fit our party of 16 (mix of kids and adults). Very comfortable hang out spaces and places to play games. The barn with the basketball court was awesome also! We got a lot of use out of that. The house was clean and everything worked well except that the dishwasher was broken. That was unfortunate, but these things happen, and we made due. The owner said that it would be fixed in a week or so, so hopefully not an issue for anyone else. Owner was...
Beautiful Berkshire Farm House on 160+ Acres

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

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

9.8 out of 10, Exceptional, (14)
"Master bath needs a taller toilet for older people Master shower needs an upgrade.."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

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

9.4 out of 10, Exceptional, (22)
"This house is on the small side but recently remodeled. Had everything we needed for a weekend stay when skiiing Catamount. A short ride to the mountain and to some great restaurants near Great Barrington made it very convenient. The location is a short walk to the lake which would be great for the summer. "
The price is SAR 731
SAR 1,417 total
includes taxes & fees
20 Feb - 21 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Comfortable Berkshires retreat on mtn resort, SISO

The price is SAR 1,208
SAR 2,524 total
includes taxes & fees
23 Feb - 24 Feb
Comfortable Berkshires retreat on mtn resort, SISO

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

10.0 out of 10, Exceptional, (65)
"Great stay! Kids and adults both loved it and very easy to access the slopes. "
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Home in Great Barrington

10.0 out of 10, Exceptional, (18)
"Our family had a wonderful experience and stay. "
The price is SAR 750
SAR 1,186 total
includes taxes & fees
24 Feb - 25 Feb
Home in Great Barrington

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (27)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...
Hudson Valley and The Berkshires getaway

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is SAR 2,430
SAR 4,113 total
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

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

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (21)
" The house has a beautiful location and the view of the lake is beautiful. There are several things to do in the surrounding areas such as hiking, horseback riding, shopping and nice restaurants. The house was overall nice. It has a combination of very nice updates and a few needed updates. The couches are extremely uncomfortable. Our host was responsive for the most part."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
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, (1762)
"Had everything we needed. Clean , fairly quiet, easy communication. We were there during this most recent snow storm. Plows were steadily clearing the road. Friendly staff. The room could use some updating as well as the gym but other than that we enjoyed our stay. "
The price is SAR 431
SAR 511 total
includes taxes & fees
23 Feb - 24 Feb
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (4)
"I had an amazing weekend.! Away from everything."
The price is SAR 469
SAR 506 total
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Eastern Catskills

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.