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Compare 429 Vacation Homes in Chatham with updated reviews, rates, and availability.

Cheerful 3-bedroom cottage with woodstove
great kitchen for cooking in
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is SAR 889
SAR 1,890 total
includes taxes & fees
6 Oct - 7 Oct
Cheerful 3-bedroom cottage with woodstove
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Welcome to River House!
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
10.0 out of 10, Exceptional, (11)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!
Amore Estate - beautiful room with many places to explore and relax in.
9.6 out of 10, Exceptional, (15)
"Our mix of family and friends had a wonderful time at your home over the Labor Day weekend. The space was clean, spacious and beautiful. The property had plenty for everyone to do. We will definitely be booking again. "
Amore Estate - beautiful room with many places to explore and relax in.
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Spectacular views and close to Great Barrington.
Private kitchen
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (213)
"We had a great stay at the carriage house! The property was incredible, we especially loved the variety of trails to explore. Our hosts were very helpful with directions and local recommendations. The house was charming and cozy. Would visit again! "
Berkshire Village Carriage House - Super Private!!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Athens Vacation Rental | 3BR | 2BA | 2 Stories | Stairs Required | 1,400 Sq Ft
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
9.4 out of 10, Exceptional, (18)
"Stayed here to attend a family wedding in Catskills. Gorgeous views despite rainy weekend. Property as described. Would stay again."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Fire place sitting area
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (36)
"We had a wonderful stay as a group of 6 adults and 2 children. The house was very comfortable and clean. We appreciated the well stocked kitchen and excellent set up for kids. The location felt private but was still only a few minutes drive from Great Barrington. Thank you for a great visit! "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
9.8 out of 10, Exceptional, (10)
"Enjoy easy access to Laurel Lake, Lenox and High Lawn Farm from this lovely space! A quick walk to the dock across the street affords time by the water to read, swim or kayak. The kitchen is nicely appointed, the house heats and cools very efficiently and the owners are wonderfully communicative. Had a great stay and would return!"
Private Access To Laurel Lake, Enjoy Lake Life
Garfield Townhouse in the Berkshires on Main St
Dining
Garfield Townhouse in the Berkshires on Main St
10.0 out of 10, Exceptional, (8)
"We very much enjoyed our stay at Garfield House and hope to be back someday. Our host Jeff was responsive and available for anything we needed. The unit was clean and set up just as shown. Highly recommend to anyone interested in staying in a great Berkshire town."
Garfield Townhouse in the Berkshires on Main St
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is SAR 983
SAR 2,004 total
includes taxes & fees
24 Sep - 25 Sep
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
the house
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
10.0 out of 10, Exceptional, (32)
"Relaxing, quiet, beautiful property. We really enjoyed the views, exploring the grounds and it is a short trip to Stockbridge. We had a wonderful stay. "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Summertime
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
10.0 out of 10, Exceptional, (41)
"Easy check-in process, very clean home. Well appointed, comfortable for 3 adults and in a quiet neighborhood. Love the wood floors and the ambiance of a treasured older home."
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Catskills Getaway w/ Hot Tub on 45 Acres!
Hannacroix Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required to Access
Catskills Getaway w/ Hot Tub on 45 Acres!
9.2 out of 10, Wonderful, (5)
"This property was a perfect location for seclusion but close enough to anything you may want! Cute and Cozy house, VERY clean and comfortable. Hot tub was AMAZING! Thank you Rich"
Catskills Getaway w/ Hot Tub on 45 Acres!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Great Barrington Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Exterior
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (105)
"House was as described. Lake was really nice. We used the 2 kayaks, pedal boat and floaty — lots of fun. There are lots of reeds and sea plants growing around the dock, so we went swimming off of the pedal boat further into the lake. Hot tub was great. Fire pit too."
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Wellspring by AvantStay | Indoor Pool + Views
Welcome!
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (6)
"The location could not be better in terms of being close to West Stockbridge yet also feeling very remote and with beautiful views. The pool was great. We thoroughly enjoyed ourselves."
Wellspring by AvantStay | Indoor Pool + Views
Near Tanglewood: Historic Summer Retreat
Living area
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (15)
"This was a beautiful, spacious, and peaceful place for us in our friends to get together. It was centrally located to everything we wanted to do. Amanda was wonderful in her communications and everything was clean and ready for us."
The price is SAR 525
SAR 1,307 total
includes taxes & fees
24 Sep - 25 Sep
Near Tanglewood: Historic Summer Retreat
Enjoy comfortable elegance in this secluded grand home located in town
Property grounds
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (64)
"Perfectly located and lovely appointments make this the place to stay when visiting Lenox, Tanglewood, etc. The home is farm in style but elegantly decorated with thoughtful combinations of old and new. Well laid out floor plan allows groups to host friends and families at the same time. You will be delighted by mornings in the kitchen or evenings in the living spaces. Enjoy! "
Enjoy comfortable elegance in this secluded grand home located in town
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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 Chatham

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 SAR 633
SAR 732 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 SAR 549
SAR 602 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"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
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.