Search Vacation Homes in Chatham

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chatham

Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Enjoyed our stay!!!"
The price is ¥22,850
¥38,965 total
includes taxes & fees
Nov 10 - Nov 11
Home in Great Barrington
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
The price is ¥25,853
¥62,653 total
includes taxes & fees
Oct 15 - Oct 16
Near Tanglewood: Historic Summer Retreat
Tiny Home w/ Hot Tub and Sunset View!
10.0 out of 10, Exceptional, (1)
"Very private and quiet, we had a wonderful time! Stars were very bright at night and we even heard coyotes in the distance! "
The price is ¥8,467
¥14,043 total
includes taxes & fees
Nov 3 - Nov 4
Tiny Home w/ Hot Tub and Sunset View!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
The price is ¥25,853
¥66,708 total
includes taxes & fees
Oct 15 - Oct 16
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is ¥30,009
¥68,913 total
includes taxes & fees
Nov 9 - Nov 10
Cheerful 3-bedroom cottage with woodstove
All the comforts of home
9.2 out of 10, Wonderful, (26)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is ¥16,056
¥21,370 total
includes taxes & fees
Oct 22 - Oct 23
All the comforts of home
Modern Luxurious Cabin, Catskills - The Tiny Nook
10.0 out of 10, Exceptional, (5)
"Great place. Exactly like the pictures. "
The price is ¥24,190
¥50,781 total
includes taxes & fees
Oct 28 - Oct 29
Modern Luxurious Cabin, Catskills - The Tiny Nook
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is ¥24,342
¥73,278 total
includes taxes & fees
Oct 15 - Oct 16
Comfortable Berkshires retreat on mtn resort, SISO
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is ¥40,992
¥74,375 total
includes taxes & fees
Oct 16 - Oct 17
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Treat yourself at the stunning June Farms Wellness Huts!
10.0 out of 10, Exceptional, (8)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
The price is ¥40,005
¥70,418 total
includes taxes & fees
Nov 5 - Nov 6
Treat yourself at the stunning June Farms Wellness Huts!
Hudson Hot Tub & Pet Escape
2.0 star property
The price is ¥20,565
¥45,748 total
includes taxes & fees
Oct 22 - Oct 23
Hudson Hot Tub & Pet Escape
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
The price is ¥45,357
¥62,655 total
includes taxes & fees
Oct 15 - Oct 16
Bungalow in the Berkshires
Catskill Stay w/ Deck & Fire Pit
8.0 out of 10, Very Good, (2)
"The house was great for a weekend trip with family. We enjoyed cooking in the kitchen, playing games in the cozy living room, and roasting up some s'mores around the bonfire at night. The location was great, close to a grocery store and some nature trails, which was important for us. We all got great sleep in the comfy bedrooms."
The price is ¥24,543
¥70,164 total
includes taxes & fees
Oct 23 - Oct 24
Catskill Stay w/ Deck & Fire Pit
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
The price is ¥34,018
¥47,962 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Great Barrington Get Away
9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is ¥43,089
¥78,529 total
includes taxes & fees
Nov 2 - Nov 3
Great Barrington Get Away
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
10.0 out of 10, Exceptional, (1)
"Perfect Hudson Valley Girls weekend! The house was gorgeous, so incredibly clean, comfortable beds, beautiful outdoor fire pit area with jacuzzi overlooking the river. All the little efforts were put into the property to make it feel like an intimate home, like providing plenty of additional towels for the jacuzzi, shampoo / conditioner in the showers and more. We were able to spend each day in Hudson downtown enjoying all the boutiques and restaurants because it was such an easy drive into...
The price is ¥44,633
¥93,153 total
includes taxes & fees
Nov 2 - Nov 3
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
The price is ¥60,476
¥100,315 total
includes taxes & fees
Nov 5 - Nov 6
Cozy. Clean. Free bagel shop.
Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
9.4 out of 10, Exceptional, (3)
"Lovely short weekend in the countryside. Calm zen retreat surrounded by nature and animals."
The price is ¥54,428
¥112,830 total
includes taxes & fees
Oct 20 - Oct 21
Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
10.0 out of 10, Exceptional, (54)
"Great spot on the lake. Super quiet and relaxing."
The price is ¥41,129
¥81,893 total
includes taxes & fees
Oct 26 - Oct 27
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed
The price is ¥32,259
¥59,518 total
includes taxes & fees
Oct 22 - Oct 23
1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
209
Accommodation
505 Vacation Homes
Lowest Price
¥14,043
Highest Price
¥112,830