Book Guest Houses in Cheshire, MA

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Top Guest Houses in Cheshire

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St, Shelburne Falls, MA
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This guesthouse includes free WiFi in public areas and a virtual front desk.
Free WiFi
Air conditioning
The Revival House

The Revival House

3 out of 5
17 Commercial St, Adams, MA
Free Cancellation
Reserve now, pay when you stay
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This guesthouse features free WiFi in public areas, a virtual front desk, and free self parking. Enjoy the free self-serve breakfast each morning. A communal living room is also provided.
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street, Lenox, MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

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Free WiFi in public areas and a garden are available at this guesthouse.
Free WiFi
Air conditioning
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

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This vacation home includes a garden and barbecue grills.
Kitchen
Free WiFi
Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home

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This guesthouse features a garden, laundry facilities, and barbecue grills.
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd, Lee, MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

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This guesthouse features laundry facilities.
Free WiFi
Air conditioning
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street, Lee, MA
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A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.
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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.

Top hotels in Cheshire

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA
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9/10 Wonderful! (1,002 reviews)

Cheshire Guest Houses essential information

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10 Guest Houses
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Popular accommodation
The Central Downtown Inn & Suites, Blooming Inn, The Revival House, The Dewey, In town, newly remodeled studio with private balcony , Berkshire Village Carriage House - Super Private!!, Guest House Sanctuary by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge

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