Search Cottages in Old Chatham

Compare 70 Cottages in Old Chatham with updated reviews, rates, and availability.

Charming Cottage in Private Lake Community (Pet-Friendly!)
Room
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.8 out of 10, Exceptional, (20)
"Cute cottage in upstate New York. Clean and stocked with the basics made it a great choice for our quick trip. Easy to find. Lovely yard with fire pit and grill. We did not have any questions or concerns but the hosts sent clear check in/out info. Highly recommend! "
Charming Cottage in Private Lake Community (Pet-Friendly!)
Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
The price is AED 918
AED 1,875 total
includes taxes & fees
24 Sep - 25 Sep
Beachwood Cottage
Charming historic cottage on scenic road to Mt. Greylock
Summer
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (101)
"We spent three nights in the Stone Schoolhouse, hiking, visiting The Clarke, and enjoying a lovely evening concert at Tanglewood. Convenient location for seeing the Berkshires, unique quarters and friendly hosts. Highly recommend!"
Charming historic cottage on scenic road to Mt. Greylock
Rose Cottage
Private kitchen
Rose Cottage
10.0 out of 10, Exceptional, (2)
"It's so peaceful there. It was lovely."
Rose Cottage
Cozy cottage with pool, walking distance to lake
Dining
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (12)
"This was our second year in a row here! We already booked for next summer! Peaceful and calm. The pool is fantastic."
Cozy cottage with pool, walking distance to lake
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (11)
"Beautiful house with amazing views. Very clean, all brand new. Great location. We would rent it again. Had an amazing Labor Day weekend. Thank you!"
Fun Getaway Lakehouse in the Hudson Valley
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (21)
"We had a wonderful time in Pittsfield for the Holidays. Sarah sent me a few different activities prior to our visit so I could plan some local holiday events ahead of time which was WONDERFUL! They were always responsive if there was an issue or question and the house was perfect."
Cozy Berkshire cottage with fireplace.
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
The gorgeous view from our back yard and note the firepit!
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
9.8 out of 10, Exceptional, (6)
"Our family of four stayed here for the weekend after picking up our daughter from Hawthorne Valley Farm Camp, and this property was perfect for us! The home was immaculate and cool when we arrived. Rudy communicated a few days ahead of time about an issue with the fridge and provided coolers and ice for us to use. We loved eating dinner out on the porch and playing board games down in the media room. The beds were clean and comfortable without being too soft. It made a huge difference that our...
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
Morgan House on Crooked Lake
Private kitchen
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
"Beautiful home on water. Perfect place to have family gatherings! Looking forward to another visit. Best area for pizza, too! ( Kay’s)"
Morgan House on Crooked Lake
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Relax on the large deck with lake views
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Hot Tub & Catskill Hiking, 15min from Hudson & Amtrak
Hot Tub & Catskill Hiking, 15min from Hudson & Amtrak
10.0 out of 10, Exceptional, (1)
"Tim and his property are fantastic!!! We literally had the best time, home was luxurious and comfortable with all attention paid to details! Looking forward to our next visit."
The price is AED 2,185
AED 3,317 total
includes taxes & fees
24 Sep - 25 Sep
Hot Tub & Catskill Hiking, 15min from Hudson & Amtrak
Cozy Catskills Home w/ Pond on 2 Acres!
Living area
Cozy Catskills Home w/ Pond on 2 Acres!
3.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely gorgeous property, the owner is awesome and can’t forget Leo the cat. "
Cozy Catskills Home w/ Pond on 2 Acres!
Spacious Historic Home in the Berkshires!
Property grounds
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior
A Charming Cottage - Secluded in Nature and Relaxing
10.0 out of 10, Exceptional, (2)
"I’ve been dreaming of a NYC getaway for years and fell in love with this home!!! I love the cozy feeling of being in such magical woods with such a beautiful lake nearby. Having access to the teepee was so special and added even more character. The beds are soooo comfortable I can’t wait to go back!!!"
A Charming Cottage - Secluded in Nature and Relaxing
Waterfalls and Trails at 'the Mills At Green Hole'
Exterior
Waterfalls and Trails at 'the Mills At Green Hole'
3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
Terrace/patio
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
3.0 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
Underhill Cottage
Interior
Underhill Cottage
Underhill Cottage
Charming Albany Retreat ~ 3 Mi to Downtown!
Living area
Charming Albany Retreat ~ 3 Mi to Downtown!
3.0 star property
Charming Albany Retreat ~ 3 Mi to Downtown!
Cottage in the Clouds With Mountain Views
Fully stocked kitchen. Two skylights provide plenty of natural light
Cottage in the Clouds With Mountain Views
9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
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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 Old Chatham

Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is AED 620
AED 717 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is AED 537
AED 589 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
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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