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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Vacation Homes in East Chatham

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 ￥33,605
￥76,391 total
includes taxes & fees
Sep 4 - Sep 5
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"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 ￥22,109
￥32,927 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!
Spacious Townhouse in 809 Park
Fridge, microwave, oven, stovetop

Spacious Townhouse in 809 Park

10.0 out of 10, Exceptional, (1)
"We had 10 people that needed a place to stay for RPI graduation. The check in process was smooth. The house clean and looked like the pictures. We enjoyed our stay."
Spacious Townhouse in 809 Park
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 ￥15,653
￥20,834 total
includes taxes & fees
Sep 1 - Sep 2
All the comforts of home
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is ￥27,415
￥75,163 total
includes taxes & fees
Aug 27 - Aug 28
Perfect House In Hillsdale, Brings Friends & Fam
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 ￥27,724
￥44,633 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥44,070
￥77,542 total
includes taxes & fees
Sep 15 - Sep 16
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is ￥55,271
￥76,227 total
includes taxes & fees
Aug 27 - Aug 28
Bungalow in the Berkshires
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 ￥30,556
￥70,344 total
includes taxes & fees
Sep 17 - Sep 18
NEW RENO Historic Creamery in Berkshires w/hot tub
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 ￥23,881
￥71,891 total
includes taxes & fees
Aug 26 - Aug 27
Comfortable Berkshires retreat on mtn resort, SISO
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Outdoor dining

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

The price is ￥26,398
￥64,484 total
includes taxes & fees
Aug 31 - Sep 1
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Charming 3-bedroom house with pool table
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom house with pool table

The price is ￥20,929
￥40,432 total
includes taxes & fees
Aug 26 - Aug 27
Charming 3-bedroom house with pool table
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 ￥34,931
￥74,085 total
includes taxes & fees
Sep 7 - Sep 8
Cheerful 3-bedroom cottage with woodstove
Bright & Airy 1 BDRM Private Apartment
Iron/ironing board, WiFi, bed sheets

Bright & Airy 1 BDRM Private Apartment

The price is ￥13,560
￥30,245 total
includes taxes & fees
Sep 8 - Sep 9
Bright & Airy 1 BDRM Private Apartment
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

The price is ￥28,181
￥47,283 total
includes taxes & fees
Aug 26 - Aug 27
3-bedroom house in beautiful Berkshires, close to amenities!
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is ￥71,484
￥118,690 total
includes taxes & fees
Aug 25 - Aug 26
The Lakeshore House
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is ￥81,285
￥155,195 total
includes taxes & fees
Aug 25 - Aug 26
Hancock Village Inn at Jiminy Peak
Glass Lake Cottage
Outdoor dining

Glass Lake Cottage

10.0 out of 10, Exceptional, (1)
"Glass lake cottage was the perfect relaxing retreat while I was visiting for a wedding at the Old Daley Inn! The place was clean, had a well stocked kitchen and everything I needed. We were lucky to catch a fantastic sunset and enjoyed the view from the large deck. Will definitely be back! "
Glass Lake Cottage
Honey Comb Hideout 3Br. House Albany
Private kitchen

Honey Comb Hideout 3Br. House Albany

The price is ￥29,478
￥63,672 total
includes taxes & fees
Aug 23 - Aug 24
Honey Comb Hideout 3Br. House Albany
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 ￥47,902
￥83,964 total
includes taxes & fees
Sep 2 - Sep 3
Great Barrington Get Away
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 East Chatham Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"It was fine , no complaints "
Roberta 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG