Search Cottages in Old Chatham

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Compare 78 Cottages in Old Chatham with updated reviews, rates, and availability.

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (24)
"The White Bunny Cottage is a charming place. It is beautifully decorated and spotless! We enjoyed making dinner and using the tableware and baskets. Perfect for entertaining family. The country setting was perfect. Very quiet. Grocery and wine shop near by. Easy access to points of interest along the Hudson River. I would highly recommend the White Bunny Cottsge. "
Charming Cottage in Private Lake Community (Pet-Friendly!)

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (13)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (22)
"We had a wonderful experience- house was clean and very comfy with all the amenities. Hosts went out of their way both before and during our stay to provide information and make sure all our needs were met! We enjoyed relaxing in the house and the location was also very close to many great Berkshires sights!! Highly recommend this listing! "
Cozy Berkshire cottage with fireplace.

Welcome to the Red Bridge Cottage!

10.0 out of 10, Exceptional, (1)
"Good experience. Love the front porch"
Welcome to the Red Bridge Cottage!

Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!

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!

Rose Cottage

9.6 out of 10, Exceptional, (5)
"Spent time relaxing working and I can"
Rose Cottage

Fun Getaway Lakehouse in the Hudson Valley

10.0 out of 10, Exceptional, (14)
"Beautiful clean property. A lovely location. Exceeded expectations."
Fun Getaway Lakehouse in the Hudson Valley

15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake

10.0 out of 10, Exceptional, (8)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
15 Minutes From Skiing/Secluded Lake Lodge on Crooked Lake

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!

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."
Beachwood Cottage

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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!

3.0 star property
Spacious Historic Home in the Berkshires!

A Charming Cottage - Secluded in Nature and Relaxing

10.0 out of 10, Exceptional, (3)
"The rental was nice. It was convenient for viewing the fall foliage and just enjoying the countryside. "
A Charming Cottage - Secluded in Nature and Relaxing

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!

3.0 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!

Underhill Cottage

Underhill Cottage

Charming Albany Retreat ~ 3 Mi to Downtown!

3.0 star property
Charming Albany Retreat ~ 3 Mi to Downtown!
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 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 634
SAR 733 total
includes taxes & fees
19 Dec - 20 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 SAR 710
SAR 779 total
includes taxes & fees
19 Dec - 20 Dec
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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