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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Guest Houses in Old Chatham

The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (316)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is AED 757
AED 845 total
includes taxes & fees
Aug 25 - Aug 26
The Dewey
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (299)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is AED 437
AED 488 total
includes taxes & fees
Jul 29 - Jul 30
The Central Downtown Inn & Suites
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (253)
"great place for "
The price is AED 735
AED 1,075 total
includes taxes & fees
Jul 31 - Aug 1
Berkshire Village Carriage House - Super Private!!
Hudson valley and The Berkshires Cottage
Exterior

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (11)
"A great stay in this well situated getaway. The owners were helpful and communicative, and the house was easy driving distance to Great Barrington, Hillsdale and Lenox. The unit is open and airy and decorated in a very pet friendly way. Would stay again without hesitation."
The price is AED 331
AED 1,169 total
includes taxes & fees
Jul 29 - Jul 30
Hudson valley and The Berkshires Cottage
Suite East Side
Interior

Suite East Side

8.6 out of 10, Excellent, (7)
"Brenda was an amazing host. The house is really cute and the decor was great. "
Suite East Side
Renovated Private Guest House by Evergreen Home
Outdoor dining

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home
Tranquil Retreat - Comfort and Convenience.
Exterior

Tranquil Retreat - Comfort and Convenience.

10.0 out of 10, Exceptional, (1)
"Incredible hosts, beautiful accommodations, will definitely be reaching out again the next time we're visiting the area!"
Tranquil Retreat - Comfort and Convenience.
1805 House Bed and Breakfast
Exterior

1805 House Bed and Breakfast

3.0 star property
9.8 out of 10, Exceptional, (38)
"Very nice stay. Perhaps a little over priced considering lack of amenities and an average breakfast."
1805 House Bed and Breakfast
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Cliffwood Cottage by Evergreen Home
Interior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Vanderbilt Lakeside
Standard Room, 1 Queen Bed, Partial Lake View | Egyptian cotton sheets, premium bedding, individually decorated

Vanderbilt Lakeside

3.5 star property
9.4 out of 10, Exceptional, (26)
"PERFECT getaway! Gracious, classy Hosts...the Inn is decorated amazingly...all of it is simply breathtaking. A lovely experience. A MUST stay!"
Vanderbilt Lakeside
Chestnut Lodge
Property grounds

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
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 Old Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was lovely."
Home 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires