Book Guest Houses in Old Chatham, NY
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Guest Houses in Old Chatham
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$94 nightly
The price is $105 total per night
$105 total
Jan 12 - Jan 13
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Jan 8 - Jan 9
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
The Dewey
7 Hubbard Street Lenox MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
Hudson valley and The Berkshires Cottage
Hillsdale NY
$344 nightly
The price is $349 total per night
$349 total
Feb 2 - Feb 3
Total with taxes and fees
A garden is available at this guesthouse.
Tranquil Retreat - Comfort and Convenience.
Delmar NY
This guesthouse features barbecue grills.
Free WiFi
Air conditioning
Renovated Private Guest House by Evergreen Home
Great Barrington MA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Pet friendly
Free WiFi
Jacob's Tanglewood Ranch
560 Stockbridge Rd Lee MA
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.
Pet friendly
Parking included
1805 House Bed and Breakfast
775 Snydertown Road Craryville NY
This guesthouse features free self parking and a terrace. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Parking included
Chestnut Lodge
75 Chestnut Street Lee MA
A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.
Hot Tub
Parking included
Cliffwood Cottage by Evergreen Home
Lenox MA
This guesthouse features laundry facilities.
Free WiFi
Air conditioning
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.
Top hotels in Old Chatham
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Old Chatham NY
9.6/10 Exceptional! (66 reviews)
Old Chatham Guest Houses essential information
Accommodation | 11 Guest Houses |
|---|---|
Lowest Price | $90 |
Highest Price | $349 |
Popular accommodation | The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, Tranquil Retreat - Comfort and Convenience., Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, 1805 House Bed and Breakfast , Chestnut Lodge, Cliffwood Cottage by Evergreen Home, Vanderbilt Lakeside |
More ways to wander Old Chatham
Explore More Ways to Travel with Travelocity
- Kinderhook Hotels
- 5 Star Hotels in Nassau
- Farmstay in Nassau
- Apartments in Nassau
- Cabins in Nassau
- Condos in Nassau
- Extended Stay Hotels in Nassau
- Hotels with Pools in Nassau
- Nassau Hotels
- Motels in Nassau
- Hotels near Art Omi International Arts Center - Fields Sculpture Park
- Hotels near The Mac-Haydn Theatre
- Country Houses in Hunter
- 3 Star Hotels in Austerlitz
- Austerlitz Hotels
- Hotels near Zema's Nursery
- New Lebanon Hotels
- Cheap Hotels in Ghent
- Pet Friendly Hotels in Ghent
- Ghent Hotels
- 5 Star Hotels in Niverville
- B&B in Niverville
- Inns in Niverville
- Lodges in Niverville
- Vacation Homes in Niverville
- Schodack Landing Hotels
- 4 Star Hotels in East Nassau
- Apartments in East Nassau
- B&B in East Nassau
- Cabins in East Nassau
- Extended Stay Hotels in East Nassau
- East Nassau Hotels
- Resorts in East Nassau
- Stephentown Hotels
- Stuyvesant Falls Hotels
- 3 Star Hotels in East Chatham
- Condos in East Chatham
- Extended Stay Hotels in East Chatham
- East Chatham Hotels
- Motels in East Chatham
- Resorts in East Chatham
- Cheap Hotels in East Greenbush
- Hotels with Hot Tubs in East Greenbush
- Hotels with an Indoor Pool in East Greenbush
- Pet Friendly Hotels in East Greenbush
- East Greenbush Hotels
- Hotels with Pools in Canaan
- Pet Friendly Hotels in Canaan
- Winery Hotels in Canaan
- Canaan Hotels
- North Chatham Hotels
- Hotels near New Lebanon Library
- 4 Star Hotels in Brainard
- Cabins in Brainard
- Extended Stay Hotels in Brainard
- Farmstay in Chatham
- B&B in Chatham
- Chalets in Chatham
- Cottages in Chatham
- Extended Stay Hotels in Chatham
- Guest Houses in Chatham
- Pet Friendly Hotels in Chatham
- Chatham Hotels
- 5 Star Hotels in Castleton-on-Hudson
- Cheap Hotels in Castleton-on-Hudson
- Hotels with Pools in Castleton-on-Hudson
- Hotels with an Indoor Pool in Castleton-on-Hudson
- Hotels with Room Service in Castleton-on-Hudson
- Pet Friendly Hotels in Castleton-on-Hudson
- Spa Resorts & in Castleton-on-Hudson
- Castleton-On-Hudson Hotels
- Farmstay in Valatie
- B&B in Valatie
- Luxury Hotels in Valatie
- Valatie Hotels
- Motels in Valatie
- Town of Schodack Hotels