Compare Chatham Guest House Rentals

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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
$94 nightly
The price is $105 total per night
$105 total
Feb 15 - Feb 16
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 1 - Feb 2
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
Free WiFi
Air conditioning
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.
Parking included
Free WiFi
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
$318 nightly
The price is $323 total per night
$323 total
Feb 2 - Feb 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 a garden and barbecue grills.
Air conditioning
Parking available
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, a garden, and barbecue grills.
Pet friendly
Free WiFi
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 picnic area. You can take advantage of free parking if you drive. Additional amenities include a communal living room and barbecue grills.
Pet friendly
Parking included
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
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
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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
    $126 nightly
    The price is $141 total per night from Feb 22 to Feb 23
    $141 total
    Feb 22 - Feb 23
    Total with taxes and fees
    8.6/10 Excellent! (2,219 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
    $169 nightly
    The price is $183 total per night from Feb 2 to Feb 3
    $183 total
    Feb 2 - Feb 3
    Total with taxes and fees
    9.4/10 Exceptional! (136 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $121 nightly
    The price is $136 total per night from Mar 1 to Mar 2
    $136 total
    Mar 1 - Mar 2
    Total with taxes and fees
    9/10 Wonderful! (818 reviews)

Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$105
Highest Price
$323
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