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Compare 400 Vacation Homes in Old Chatham with updated reviews, rates, and availability.

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is $159
$335 total
includes taxes & fees
Jun 30 - Jul 1
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cozy Retreat on Copake Lake in our Charming Home
Pool
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (32)
"Great stay. A short walk to everything the lake has to offer."
Cozy Retreat on Copake Lake in our Charming Home
Spectacular views and close to Great Barrington.
Living area
Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
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Hearts Desire is a furnished whole house in a small, colorful garden center.
Terrace/patio
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (69)
"What an amazing find to stay at while attending a yoga festival at Jiminy Peak. The house was immaculate and didn't miss a thing! Not only was there a bottle of wine waiting, but an adorable history of the home. The house was HUGE and the beds very comfortable. I wouldn't call it a 3 bedroom house though, it's a 2 bedroom with a pull out sofa in the living room. The hot tub is amazing and watching the starts and fireflies in the backyard at night was magical. Highly recommend and would stay...
Hearts Desire is a furnished whole house in a small, colorful garden center.
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
Exterior
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
9.8 out of 10, Exceptional, (60)
"This was the 2nd time we have rented this property and again it did not disappoint. The location on the mountain is beautiful. The check in/check out process was easy. The host (Howie) responds to any questions very quickly and enthusiastically. Perfect place for a family with spacious bedrooms, nice kitchen, back deck with grill. Looking forward to going back"
The price is $349
$644 total
includes taxes & fees
Jun 30 - Jul 1
Gorgeous 3BR 3BA Sleeps 8 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Condo
3 Bedroom Lakefront Home with Hot Tub & Fireplace
View from property
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (98)
"Well appointed, clean, comfortable for 6, with enough space and chairs at the table for 8 at dinner. The location is right on the lake with a deck that looks over the water. Wifi was strong enough for us to work remotely. Owner was quick and responsive to fix our slow draining sink. Location was only a few minutes drive into Troy as we were there for the graduation, which made it convenient."
3 Bedroom Lakefront Home with Hot Tub & Fireplace
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Shower, hair dryer, towels
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (10)
"The number of bedrooms and bathrooms was great for the 13 of us. The big kitchen, pantry and long dining tables made for fun interaction. The game room with pool table and ping pong table were perfect for after dinner fun. Beautiful property on the river. We plan to go back. Historic homes are tough to maintain and our hope is that it is as nice in the future as it was this week."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Chic Pittsfield Home With A View!
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
2 bedroom town house with game room
Fridge, microwave, oven, stovetop
2 bedroom town house with game room
6.0 out of 10, (8)
"Property was easy to get to. Located right off the thruway. House was clean and located close to plenty of shopping options. There was also fast food restaurants located within walking distance. "
The price is $85
$145 total
includes taxes & fees
Jun 26 - Jun 27
2 bedroom town house with game room
Conveniently located by HVCC. No cleaning or pet fee
Property grounds
Conveniently located by HVCC. No cleaning or pet fee
9.6 out of 10, Exceptional, (17)
"We arrived and didnt know what to expect. Everyone proceeded to choose the room that seemed to just fit. We enjoyed the opportunity to sit fireside and plan our days and even had a cook out. Nobody had any complaint about the house. If it were my property i would suggest a no shoes policy. I cant think of any other place i would prefer to stay . It was safe, the neighbors were very nice and our host was the best. Thank you for everything."
Conveniently located by HVCC. No cleaning or pet fee
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Fridge, oven, stovetop, dishwasher
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (4)
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Modern-Chic Athens Home - Fish, Ski & Swim!
Fridge, microwave, stovetop, coffee/tea maker
Modern-Chic Athens Home - Fish, Ski & Swim!
10.0 out of 10, Exceptional, (8)
"The house was great. It's new and had everything we needed/wanted. Thre was a small deck where the BBQ grill was located and there were plenty of seats and tables on the lawn. We had a great time BBQing. The yard was not fenced, but had natural vegetation separting it from the other properties. We loved the community pool/beach/tennis court. The pool/beach was just a few houses down. The doggy beach was small, but that didn't stop our dog from going swimming. The community dog park was not...
Modern-Chic Athens Home - Fish, Ski & Swim!
Private Access To Laurel Lake, Enjoy Lake Life
Property grounds
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."
Private Access To Laurel Lake, Enjoy Lake Life
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Game room
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, (107)
"Our party of four adults found ample space to spread out and relax at this property. There are quite a few stairs to access all three stories, including the main living space on the second story and the four bedrooms on the third story. The kitchen is well equipped and there is a charcoal grill (bring your own charcoal). There is a very nice deck overlooking the lovely and sprawling grounds below the house. A fire pit was situated behind the house. There is a balcony and patio also off the...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Cottage at Copake Lake
Property grounds
Cottage at Copake Lake
9.8 out of 10, Exceptional, (57)
"We have enjoyed several stays in this wonderful cottage…usually in the winter. We were so delighted sitting on the porch in the evenings listening to the chorus of frogs by the lake. Absolutely enchanting! Ellen is a wonderful hostess. The cottage is immaculate and well stocked. Hopefully we will visit this cozy cottage again!"
Cottage at Copake Lake
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Property grounds
Waterfront Escape +dock +kayaks +firepit +fireplace +games
10.0 out of 10, Exceptional, (4)
"Great place with lake access & sunset views. Swimming/diving dock wasn't there due to low lake levels, but beach club right next door had a nice place to swim. Kitchen could've used a baking sheet and some olive oil, but other than had everything we needed!"
Waterfront Escape +dock +kayaks +firepit +fireplace +games
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (25)
"Beautiful property- well maintained and excellent location."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
All the comforts of home
Fridge, microwave, oven, stovetop
All the comforts of home
9.0 out of 10, Wonderful, (19)
"Great little place to get away Steven was a great host"
The price is $118
$147 total
includes taxes & fees
Jun 26 - Jun 27
All the comforts of home
Hudson Valley Chalet
Property grounds
Hudson Valley Chalet
9.2 out of 10, Wonderful, (5)
"We had such a nice weekend at this beautiful home! The location was great, there were awesome views, and Marc was a very kind, courteous host! He was very easy to get ahold of if we had any questions. The hot tub was very relaxing and spacious. Also, it had all of the necessities. If you are looking for a family-friendly winter rental this is a great place to book."
Hudson Valley Chalet
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Interior
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, (12)
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
Peaceful Retreat Compound 10 Minutes to Great Barrington!
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See all available properties in Old Chatham
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.

Other property types in Old Chatham

Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
Fridge, microwave, oven, stovetop
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
9.6 out of 10, Exceptional, (80)
"We loved our stay over Memorial Day weekend. We were three families and fit well in the home with 6 adults, 8 teens and 1 child. Kids loved the pool (it's on the cool side with no heater). The landscaping on the property is so gorgeous. The home itself is very comfortable with many places to spend time together - our favorite is the screened in porch. The two master suites is neat with each having two bedroom spaces per suite. It would be great with a family who wants to have young children...
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is $151
$166 total
includes taxes & fees
Jun 26 - Jun 27
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (74)
"Expedia said they have a Sunday buffet, but they didn't."
The price is $125
$141 total
includes taxes & fees
Jun 26 - Jun 27
Micosta Leisure Inn
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.

Old Chatham Vacation Homes information

Number of reviews
547
Accommodation
400 Vacation Homes
Lowest Price
$85
Highest Price
$349

Recent reviews of Old Chatham hotels
Expedia verified reviews

Hyatt Place Albany

Hyatt Place Albany

5/5 Excellent
"The hotel was clean, and beautiful. The staff were kind and respectful. "
A verified traveler stayed at Hyatt Place Albany
Posted 2 days ago
Hyatt Place Albany