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Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Vacation Homes in Chatham

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (257)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AED 551
AED 837 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!
All the comforts of home
Property grounds

All the comforts of home

9.0 out of 10, Wonderful, (24)
"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 AED 390
AED 519 total
includes taxes & fees
2 Sep - 3 Sep
All the comforts of home
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is AED 612
AED 1,015 total
includes taxes & fees
3 Sep - 4 Sep
Home in Great Barrington
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AED 988
AED 1,822 total
includes taxes & fees
11 Sep - 12 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is AED 749
AED 1,739 total
includes taxes & fees
2 Sep - 3 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Modern Luxurious Cabin, Catskills - The Tiny Nook
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

10.0 out of 10, Exceptional, (5)
"The place was clean and just like the pictures. The hosts we great and communication was great. Definitely will stay here again. Already recommended it to a few friends!"
The price is AED 588
AED 1,254 total
includes taxes & fees
3 Sep - 4 Sep
Modern Luxurious Cabin, Catskills - The Tiny Nook
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is AED 837
AED 1,875 total
includes taxes & fees
2 Sep - 3 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is AED 871
AED 1,846 total
includes taxes & fees
9 Sep - 10 Sep
Cheerful 3-bedroom cottage with woodstove
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AED 591
AED 1,760 total
includes taxes & fees
2 Sep - 3 Sep
Comfortable Berkshires retreat on mtn resort, SISO
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is AED 749
AED 1,666 total
includes taxes & fees
3 Sep - 4 Sep
Near Tanglewood: Historic Summer Retreat
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is AED 1,377
AED 1,859 total
includes taxes & fees
2 Sep - 3 Sep
Bungalow in the Berkshires
Treat yourself at the stunning June Farms Wellness Huts!
Terrace/patio

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."
Treat yourself at the stunning June Farms Wellness Huts!
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Private kitchen

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is AED 1,781
AED 2,958 total
includes taxes & fees
2 Sep - 3 Sep
The Lakeshore House
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
Smart TV, books, stereo

Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson

9.6 out of 10, Exceptional, (8)
"Great space for our family of four and dog. Lots of room to spread out and relax. Nice local events going on and great location to stores and short drive to hiking spots and many restaurants. Host had great communication with us and answered all of our questions in a really timely manner. Definitely recommend this spot!"
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,847 total
includes taxes & fees
2 Sep - 3 Sep
Hancock Village Inn at Jiminy Peak
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

3-bedroom house in beautiful Berkshires, close to amenities!

The price is AED 752
AED 1,214 total
includes taxes & fees
1 Oct - 2 Oct
3-bedroom house in beautiful Berkshires, close to amenities!
Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
Dining

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 AED 1,322
AED 2,741 total
includes taxes & fees
8 Sep - 9 Sep
Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly
Great Barrington Get Away
Fridge, microwave, oven, stovetop

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 AED 1,102
AED 1,953 total
includes taxes & fees
1 Oct - 2 Oct
Great Barrington Get Away
Serene Estate: Heated Pool, Tennis, Sauna, Hot Tub
Interior

Serene Estate: Heated Pool, Tennis, Sauna, Hot Tub

The price is AED 3,122
AED 4,845 total
includes taxes & fees
15 Sep - 16 Sep
Serene Estate: Heated Pool, Tennis, Sauna, Hot Tub
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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Top Chatham Hotel Reviews

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