Search Cottages in Chatham

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

This weekend
Interior
Catskill Cottage, Walk to Downtown & River Views
10.0 out of 10, Exceptional, (1)
"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 HK$696
per night
5 May - 6 May
Catskill Cottage, Walk to Downtown & River Views
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 HK$1,564
per night
23 May - 24 May
The Blue Elm - A Historic Berkshire Cottage
Fridge, microwave, oven, stovetop
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
10.0 out of 10, Exceptional, (2)
"Had a wonderful time at the cottage - just a short walk to everything hudson has to offer but off the main drag with a private with valley views to the south. We felt well taken care of. Would come back for sure."
Sunset Cottage: 3 bedrooms, sleeps 6, views, pet friendly, firepit, media room!
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Charming unique cottage Relax & enjoy the stunning mountains with private views!
10.0 out of 10, Exceptional, (17)
"We enjoyed our stay along with our dogs at the Gazebo. Beautiful mountain views and peaceful environment. Plenty of hiking and quiet country roads to walk the dogs. The cottage is very quaint and tastefully decorated. We hope to be back again."
Charming unique cottage Relax & enjoy the stunning mountains with private views!
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, (7)
"Nicely renovated house. A few issues likely caused by an ice storm prior to our arrival. Owner was kind to resolve. Beds are VERY firm, if that is your thing. There are new window coverings in the bedrooms, but room darkening would have been a huge plus. No sleeping in if you are at all light sensitive. An App on the tv that would allow for streaming network channels would also be great."
Fun Getaway Lakehouse in the Hudson Valley
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
Smart TV, fireplace
Round House
10.0 out of 10, Exceptional, (2)
"Beautiful location and very comfortable private location. Highly recommend"
Round House
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
Smart TV, fireplace, books
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful location. Lots of hiking nearby. Countless places, towns, attractions, etc. to check out. The house was better than the pictures suggest. We are already making plans to return in the Spring / Summer."
Summer Cottage on 5-acre woods w Games & BBQ, 20 min to Hudson
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!
Fridge, microwave, oven, stovetop
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
Property grounds
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
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
The Blue Jay - a New England Cottage
9.8 out of 10, Exceptional, (6)
"The cabin was as advertised and super clean. We had a great time exploring the area."
The Blue Jay - a New England Cottage
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!)
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

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, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1672)
"Very nice spot quiet "
The price is HK$1,319
per night
4 May - 5 May
Vacation Village in the Berkshires
Private kitchen
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (856)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is HK$1,164
per night
8 May - 9 May
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.

Chatham Cottages information

Number of reviews
224
Accommodation
91 Cottages
Lowest Price
HK$696
Highest Price
HK$1,564

Recent Hotel Reviews in Chatham
Expedia verified reviews