Compare Chatham Guest House Rentals

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Featured Guest Houses in Chatham

Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $169 total per night
$169 total
Jul 13 - Jul 14
Total with taxes and fees
At Hideaway Inn Lenox, guests have access to free WiFi in public areas, microwave in a common area, and an arcade/game room. Free parking is available if you drive. Other amenities at this family-friendly guesthouse include a library, a communal living room, and a vending machine.
Pet friendly
Parking included
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$110 nightly
The price is $122 total per night
$122 total
Jul 27 - Jul 28
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
$240 nightly
The price is $268 total per night
$268 total
Jul 15 - Jul 16
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
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
LEEDS A GREAT ESCAPE

LEEDS A GREAT ESCAPE

Leeds NY
Guests staying at this guesthouse have access to barbecue grills and a garden.
Air conditioning
Parking available
Hudson valley and The Berkshires Cottage

Hudson valley and The Berkshires Cottage

Hillsdale NY
$350 nightly
The price is $355 total per night
$355 total
Jul 15 - Jul 16
Total with taxes and fees
At this guesthouse, guests have access to a garden.
Pet friendly
Free WiFi
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
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
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 barbecue grills. You can take advantage of free parking if you drive. Additional amenities include a picnic area and a communal living room.
Pet friendly
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

    Country Inn & Suites by Radisson, Downtown Albany New York

    Country Inn & Suites by Radisson, Downtown Albany New York

    300 Broadway Albany NY
    $101 nightly
    The price is $116 total per night from Aug 2 to Aug 3
    $116 total
    Aug 2 - Aug 3
    Total with taxes and fees
    8/10 Very Good! (801 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $143 nightly
    The price is $159 total per night from Jul 13 to Jul 14
    $159 total
    Jul 13 - Jul 14
    Total with taxes and fees
    8.8/10 Excellent! (2,432 reviews)
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $151 nightly
    The price is $169 total per night from Jul 13 to Jul 14
    $169 total
    Jul 13 - Jul 14
    Total with taxes and fees
    9.2/10 Wonderful! (1,013 reviews)

Chatham Guest Houses essential information

Accommodation
12 Guest Houses
Lowest Price
$116
Highest Price
$355
Popular accommodation
Hideaway Inn Lenox, The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, LEEDS A GREAT ESCAPE, Hudson valley and The Berkshires Cottage, Renovated Private Guest House by Evergreen Home, Cliffwood Cottage by Evergreen Home, Jacob's Tanglewood Ranch

More to Explore