Compare Cheshire Guest House Rentals

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Featured Guest Houses in Cheshire

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
The price is $114 total per night
$114 total
per night
Apr 19 - Apr 20
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
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
The price is $170 total per night
$170 total
per night
Apr 21 - Apr 22
Blooming Inn features free WiFi in public areas, coffee in a common area, and refrigerator in a common area. You can put free offsite parking to good use if you drive.
Free WiFi
Air conditioning
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
The price is $207 total per night
$207 total
per night
Apr 18 - Apr 19
Guests staying at this guesthouse have access to a garden and barbecue grills.
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
The price is $168 total per night
$168 total
per night
Apr 19 - Apr 20
The Revival House features free WiFi in public areas and a communal living room. There's free parking if you drive.
Breakfast included
Parking included
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
The price is $156 total per night
$156 total
per night
Apr 27 - Apr 28
This guesthouse features free WiFi in public areas and a garden.
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
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
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 Cheshire

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $110 nightly
    The price is $123 total per night from Apr 19 to Apr 20
    $123 total
    Apr 19 - Apr 20
    Total with taxes and fees
    8.8/10 Excellent! (2,334 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $133 nightly
    The price is $149 total per night from May 14 to May 15
    $149 total
    May 14 - May 15
    Total with taxes and fees
    8.8/10 Excellent! (1,001 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $108 nightly
    The price is $120 total per night from May 17 to May 18
    $120 total
    May 17 - May 18
    Total with taxes and fees
    9/10 Wonderful! (906 reviews)

Cheshire Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$114
Highest Price
$207
Popular accommodation
The Central Downtown Inn & Suites, Blooming Inn, Berkshire Village Carriage House - Super Private!!, The Revival House, In town, newly remodeled studio with private balcony , The Dewey, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge

More to Explore