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
$102 nightly
The price is $114 total per night
$114 total
Apr 13 - Apr 14
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
$185 nightly
The price is $207 total per night
$207 total
Apr 13 - Apr 14
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
$306 nightly
The price is $309 total per night
$309 total
Apr 20 - Apr 21
Total with taxes and fees
At this guesthouse, guests have access to a garden.
Pet friendly
Free WiFi
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
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, barbecue grills, and a garden.
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 communal living room. You can take advantage of free parking if you drive. Additional amenities include a picnic area and barbecue grills.
Pet friendly
Parking included
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
At this guesthouse, guests have access to features like laundry facilities.
Free WiFi
Air conditioning
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
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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 Apr 13 to Apr 14
    $141 total
    Apr 13 - Apr 14
    Total with taxes and fees
    8.8/10 Excellent! (2,332 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
    $167 nightly
    The price is $180 total per night from Apr 20 to Apr 21
    $180 total
    Apr 20 - Apr 21
    Total with taxes and fees
    9.6/10 Exceptional! (198 reviews)
    Country Inn & Suites by Radisson, Downtown Albany New York

    Country Inn & Suites by Radisson, Downtown Albany New York

    300 Broadway Albany NY
    $113 nightly
    The price is $129 total per night from Apr 19 to Apr 20
    $129 total
    Apr 19 - Apr 20
    Total with taxes and fees
    8/10 Very Good! (572 reviews)

Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$114
Highest Price
$309
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, Hudson valley and The Berkshires Cottage, The Dewey, LEEDS A GREAT ESCAPE, Renovated Private Guest House by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, 1805 House Bed and Breakfast

More to Explore