Compare Chatham Guest House Rentals

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Featured Guest Houses in Chatham

The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street, Lenox, MA
$216 nightly
The price is $241 total per night
$241 total
Aug 13 - Aug 14
Total includes taxes and fees
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.
Parking included
Free WiFi
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
$129 nightly
The price is $144 total per night
$144 total
Jul 22 - Jul 23
Total includes 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!!

$262 nightly
The price is $293 total per night
$293 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests staying at this vacation home have access to a garden and barbecue grills.
Kitchen
Free WiFi
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

$328 nightly
The price is $331 total per night
$331 total
Jul 28 - Jul 29
Total includes taxes and fees
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Pet friendly
Free WiFi
LEEDS A GREAT ESCAPE

LEEDS A GREAT ESCAPE

Guests staying at this guesthouse have access to barbecue grills and a garden.
Air conditioning
Parking available
Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Pet friendly
Free WiFi
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 garden, and a picnic area. You can put free parking to good use if you drive. Multilingual staff is on hand to answer questions.
Breakfast included
Parking included
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 fireplace in the lobby. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
Pet friendly
Parking included
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

At this guesthouse, guests have access to features like laundry facilities.
Free WiFi
Air conditioning
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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
    $110 nightly
    The price is $123 total per night from Aug 4 to Aug 5
    $123 total
    Aug 4 - Aug 5
    Total includes taxes and fees
    8.6/10 Excellent! (1,887 reviews)
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    190 Meadow Street, South Lee, MA
    $178 nightly
    The price is $199 total per night from Jul 23 to Jul 24
    $199 total
    Jul 23 - Jul 24
    Total includes taxes and fees
    9/10 Wonderful! (676 reviews)
    Berkshires Untold

    Berkshires Untold

    194 Pittsfield Rd, Lenox, MA
    $199 nightly
    The price is $223 total per night from Jul 22 to Jul 23
    $223 total
    Jul 22 - Jul 23
    Total includes taxes and fees
    9/10 Wonderful! (640 reviews)

Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$123
Highest Price
$331
Popular accommodation
The Dewey, The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, Hudson valley and The Berkshires Cottage, LEEDS A GREAT ESCAPE, Renovated Private Guest House by Evergreen Home, 1805 House Bed and Breakfast , Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home

Guest Houses in Chatham

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