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Compare 91 Cottages in Chatham with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
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!)
Interior
Catskill Cottage, Walk to Downtown & River Views
10.0 out of 10, Exceptional, (2)
"This cottage was so perfect! The location was amazing and walkable to all the shops and restaurants. Host was easy to correspond with, and the house had everything we needed. We would love to come back again some day!"
The price is $89
$159 total
includes taxes & fees
May 20 - May 21
Catskill Cottage, Walk to Downtown & River Views
Interior
Cozy Catskills Home w/ Pond on 2 Acres!
3.0 star property
10.0 out of 10, Exceptional, (1)
"There is nothing we didnt like i would recommend this place to anyone. It was clean, quiet, close to everything but far enough away to feel private. We will be back again."
Cozy Catskills Home w/ Pond on 2 Acres!
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Outdoor dining
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (32)
"Quaint cabin tucked away in the Berkshires. For those vacationing with a pet, be aware that on Labor Day weekend this neighborhood puts on a fireworks show right by this house. Also, there really is not any yard, just a small patio. Lots of great hiking in the area."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Fridge, microwave, oven, stovetop
Cottage in the Berkshires 10 min. to Great Barrington
Cottage in the Berkshires 10 min. to Great Barrington
Fridge, microwave, oven, stovetop
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
10.0 out of 10, Exceptional, (3)
"Property is a convenient 5 minute walk to the heart of Warren Street. Home was as described - clean & cozy with a nice porch and ample parking for several cars. Only suggestion would be to trim the trees that block the view of the Hudson … if they are on the property. We visited in the Spring when the leaves were on the trees. The.view of the Hudson might be fine in Winter."
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
Exterior
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is $200
$413 total
includes taxes & fees
May 23 - May 24
The Blue Elm - A Historic Berkshire Cottage
Exterior
Rose Cottage
Rose Cottage
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Loblolly Cottage - Enchanting Retreat set among towering pines.
9.8 out of 10, Exceptional, (28)
"This is a beautiful, cozy, and comfortable cottage. The attention to design detail, stained glass windows in the peaks, lantern wall lights, and barn wood beams, makes this a special place. We were there on a cold and rainy weekend and it was a perfect place to just relax. "
Loblolly Cottage - Enchanting Retreat set among towering pines.
Fridge, microwave, oven, stovetop
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...
Quiet rustic cottage with shared lake access
Property grounds
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
Outdoor pool
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
Beach
Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (7)
"The Catskill Nook is beautiful and cozy with all the ameneties on the inside. And on the outside it's just a short walk away from main street with shops, bars and restaurants. Owners have thought of everything, and communication was effortless and very welcoming."
Charming Cottage in the Heart of Catskill & Pet Friendly
Property grounds
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
Fridge, microwave, oven, stovetop
Spacious Cottage Retreat on Beautiful 2-Acres
Spacious Cottage Retreat on Beautiful 2-Acres
Fridge, microwave, oven, stovetop
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.
Beach nearby, sun loungers
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
Property grounds
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!
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."
Beachwood Cottage
Fridge, microwave, oven, stovetop
Caretaker's Cottage: 20 minutes to Tanglewood
10.0 out of 10, Exceptional, (3)
"Excellent home, beautiful views, no issues."
Caretaker's Cottage: 20 minutes to Tanglewood
Don't see what you're looking for?
See all available properties in 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 Chatham

Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $149
$163 total
includes taxes & fees
May 18 - May 19
Jiminy Peak Mountain Resort
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (72)
"super nice and clean I think I will return the only thing is that it is under construction."
The price is $125
$141 total
includes taxes & fees
May 19 - May 20
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.

Chatham Cottages information

Number of reviews
225
Accommodation
91 Cottages
Lowest Price
$89
Highest Price
$200

Frequently asked questions

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Reserving a cottage in Chatham is as simple as working out your travel dates and choosing your ideal place for outdoor relaxation and recreation. From upscale retreats to affordable stays and cottages that come with perks like a hot tub, Expedia has something for all tastes and styles. As for terrific deals? We have them too!
How can I find cheap cottages in Chatham?
With Expedia’s helpful filter tool, comparing cheap cottages in Chatham is a cinch. To find stays that’ll make your wallet happy, narrow your search results by budget, star rating and amenities.
What is there to do in Chatham near my cottage?
You’ll find plenty of awesome things to sink your teeth into in Chatham. Check out leading attractions like The Mac-Haydn Theatre, Hudson Chatham Winery and Shaker Museum and Library. Kinderhook Lake, Van Alen House and High Falls Trail are also on many to-do lists.

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