Compare Chatham Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Chatham

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$102 nightly
The price is $114 total per night
$114 total
Mar 10 - Mar 11
Total with taxes and fees
Guests of The Central Downtown Inn & Suites enjoy free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide luggage storage. Additional amenities include a terrace and laundry facilities.
Pet friendly
Parking included
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Feb 26 - Feb 27
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
$317 nightly
The price is $322 total per night
$322 total
Mar 2 - Mar 3
Total with taxes and fees
At this guesthouse, guests have access to a garden.
Pet friendly
Free WiFi
LEEDS A GREAT ESCAPE

LEEDS A GREAT ESCAPE

Leeds NY
Guests staying at this guesthouse have access to barbecue grills and a garden.
Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

Great Barrington MA
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd Lee MA
Guests staying at Jacob's Tanglewood Ranch enjoy free WiFi in public areas, a terrace, and a communal living room. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
1805 House Bed and Breakfast

1805 House Bed and Breakfast

3 out of 5
775 Snydertown Road Craryville NY
Guests staying at 1805 House Bed and Breakfast have access to a terrace, a picnic area, and a garden. You can put free parking to good use if you drive. Multilingual staff is on hand to answer questions.
Breakfast included
Parking included
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
At Chestnut Lodge, guests have access to free WiFi in public areas, a hot tub, and a terrace. A stay here includes free parking. This smoke-free guesthouse also has a picnic area.
Hot Tub
Parking included
Don't see what you're looking for?
See all available properties in Chatham
View all properties
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.

Hotel Options in Chatham

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $128 nightly
    The price is $143 total per night from Feb 26 to Feb 27
    $143 total
    Feb 26 - Feb 27
    Total with taxes and fees
    8.8/10 Excellent! (2,266 reviews)
    Comfort Inn Glenmont - Albany South

    Comfort Inn Glenmont - Albany South

    37 Route 9W Glenmont NY
    $82 nightly
    The price is $94 total per night from Mar 9 to Mar 10
    $94 total
    Mar 9 - Mar 10
    Total with taxes and fees
    7.8/10 Good! (1,002 reviews)
    Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

    Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

    282 Cairo Junction Rd Catskill NY
    $149 nightly
    The price is $161 total per night from Feb 26 to Feb 27
    $161 total
    Feb 26 - Feb 27
    Total with taxes and fees
    9.6/10 Exceptional! (159 reviews)

Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$94
Highest Price
$322
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, Hudson valley and The Berkshires Cottage, LEEDS A GREAT ESCAPE, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, 1805 House Bed and Breakfast , Chestnut Lodge

More to Explore