Search Cottages in Old Chatham

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Compare 73 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!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Rose Cottage
Private kitchen
Rose Cottage
Rose Cottage
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Property grounds
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Sunny Lakeside Artist's Cottage with Dock and Kayaks
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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, (95)
"A great place in a great location with super-responsive and helpful owners! My partner is a teacher and she was entranced with the schoolroom, the history, and the old textbooks!"
Charming historic cottage on scenic road to Mt. Greylock
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!
9.6 out of 10, Exceptional, (5)
"We were a bit sweltering in the heat, as the AC Units hadn't been installed yet. Rudy was very communicative in terms of getting help, but I was a little surprised that there weren't people readily available to assist should something that affected the stay that much come up. Thankfully the units were installed by the second night. Otherwise, the cottage is a lovely spot and an easy walk from Warren Street."
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
Cozy Cottage in the Woods
Dining
Cozy Cottage in the Woods
10.0 out of 10, Exceptional, (1)
"I have nothing but great things to say about our stay! Our hosts were great and very welcoming. The property was beautiful and our cottage as well. We will most definitely be back! Thank you!"
Cozy Cottage in the Woods
Cozy cottage with pool, walking distance to lake
Dining
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (11)
"Very clean property with nice amenities near beautiful lake. Beds were comfortable owner very helpful with anything you might need"
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, (8)
"This was an excellent stay in a perfect location to explore both the Hudson Valley and the Berkshires. Host communicated seamlessly, and house is precisely as described. Very spacious and furnished in a neutral tones, minimalist style. Would recommend."
Fun Getaway Lakehouse in the Hudson Valley
Spacious Cottage Retreat on Beautiful 2-Acres
Spacious Cottage Retreat on Beautiful 2-Acres
10.0 out of 10, Exceptional, (2)
"We were attending a family wedding in Stuyvesant and this sweet cottage was a great place to relax after all the festivities. This sweet retreat is so comfortable, very private and neatly decorated. Our hosts were great about checking in with us during our stay. Will definitely stay here again next time!"
Spacious Cottage Retreat on Beautiful 2-Acres
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
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, (2)
"The house is very cozy with a well appointed kitchen and a beautiful view of the lake. We would like to go back some day. The host is very responsive and kind."
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Cozy Berkshires Cottage w/ 11 Private Acres!
Lee Vacation Rental | 1BR | 1BA | 1,300 Sq Ft | Steps Required
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
The price is SAR 1,032
SAR 2,028 total
includes taxes & fees
8 Jul - 9 Jul
8 Raj. - 9 Raj.
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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!
Waterfalls and Trails at 'the Mills At Green Hole'
Exterior
Waterfalls and Trails at 'the Mills At Green Hole'
3.5 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!
3.5 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
Cottage in the Clouds With Mountain Views
Fully stocked kitchen. Two skylights provide plenty of natural light
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
"A sanctuary for writers and astronomers! Exquisite cottage and surroundings. Short hop to all that goes on in the Berkshires. You won't want to leave!"
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.

Other property types in Old Chatham

Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
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
Property entrance
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 SAR 596
SAR 654 total
includes taxes & fees
23 Jun - 24 Jun
23 Jum. II - 24 Jum. II
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Terrace/patio
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (74)
"Only stayed one night, but would have loved to stay for one week! Beautiful grounds and our host, Steven, was super welcoming and greeted us once we arrived to check us in. Local cat also greeted us once we arrived (if you’re driving, check under your car before backing out!)"
The price is SAR 470
SAR 528 total
includes taxes & fees
23 Jun - 24 Jun
23 Jum. II - 24 Jum. II
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.

Recent reviews of Old Chatham hotels
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Loved the lake in the back !!!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 2 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection