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
$104 nightly
The price is $116 total per night
$116 total
Oct 31 - Nov 1
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
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street, Lenox, MA
$185 nightly
The price is $207 total per night
$207 total
Oct 29 - Oct 30
Total with 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
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

$205 nightly
The price is $229 total per night
$229 total
Oct 28 - Oct 29
Total with 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

$310 nightly
The price is $315 total per night
$315 total
Oct 6 - Oct 7
Total with 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 a garden and barbecue grills.
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
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
    $86 nightly
    The price is $96 total per night from Nov 2 to Nov 3
    $96 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.6/10 Excellent! (2,028 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (668 reviews)
    Comfort Inn Glenmont - Albany South

    Comfort Inn Glenmont - Albany South

    37 Route 9W, Glenmont, NY
    $93 nightly
    The price is $106 total per night from Nov 2 to Nov 3
    $106 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (1,006 reviews)

Chatham Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$96
Highest Price
$315
Popular accommodation
The Central Downtown Inn & Suites, The Dewey, 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, Chestnut Lodge

More to Explore

More to Explore