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Next weekend

18 Rab. II - 20 Rab. II

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25 Rab. II - 27 Rab. II

In one month

9 Jum. I - 11 Jum. I

In two months

6 Jum. II - 8 Jum. II

Compare 539 Vacation Homes in Chatham with updated reviews, rates, and availability.

"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "

SAR 859 total

includes taxes & fees

10 Apr - 11 Apr

"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...

SAR 3,886 total

includes taxes & fees

11 Apr - 12 Apr

"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."

"We had a lovely stay. Views are amazing. Property owner was very responsive and helpful. Would love to go back in the fall."

"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"

SAR 1,310 total

includes taxes & fees

14 Apr - 15 Apr

"This was the perfect cozy home for a few nights away. Gorgeous property and welcoming vibes. "

"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "

"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"

"Bassinova-on-Hudson is a gorgeous and well-kept property, and Jean and her staff are very responsive and welcoming. The home features everything a group could want in a secluded getaway - a gated, private entrance, 5 bedrooms, a game room with billiards table, a home theater, sonos throughout the house, a steam shower, and an enormous kitchen and outdoor grill.When I arrived with my wife and 19 month old, Kat gave us a quick tour of the house and explained how everything worked, and the basic...

"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"

"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"

"The property was centrally located for skiing, and was a comfortable stay."

SAR 1,644 total

includes taxes & fees

7 May - 8 May

"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."

"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "

"The location was great and just a short walk to downtown. We thought the pictures on the site were a bit misleading. The house looked a little more open than it actually was, especially in the kitchen. The outside fire pit area was a little run down. A chair was broken and the string lights were down on the ground, water filled and no outlet to plug into. Plenty of bed space for everyone to sleep and beds were comfortable. Plenty of extra sheets and towels and the kitchen was well equipped. We...

"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."

"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"

"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. "

"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "

"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...