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
$85 nightly
The price is $95 total per night
$95 total
Nov 25 - Nov 26
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.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$189 nightly
The price is $211 total per night
$211 total
Nov 25 - Nov 26
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
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
$307 nightly
The price is $312 total per night
$312 total
Dec 17 - Dec 18
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
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, a garden, and barbecue grills.
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.
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.
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.
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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
    $94 nightly
    The price is $105 total per night from Nov 25 to Nov 26
    $105 total
    Nov 25 - Nov 26
    Total with taxes and fees
    8.6/10 Excellent! (2,136 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $99 nightly
    The price is $110 total per night from Dec 7 to Dec 8
    $110 total
    Dec 7 - Dec 8
    Total with taxes and fees
    9/10 Wonderful! (763 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $87 nightly
    The price is $97 total per night from Dec 23 to Dec 24
    $97 total
    Dec 23 - Dec 24
    Total with taxes and fees
    7.8/10 Good! (962 reviews)

Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$95
Highest Price
$312
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