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
$114 nightly
The price is $127 total per night
$127 total
Jun 7 - Jun 8
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 Revival House

The Revival House

3 out of 5
17 Commercial St Adams MA
Free Cancellation
Reserve now, pay when you stay
$166 nightly
The price is $185 total per night
$185 total
Jun 16 - Jun 17
Total with taxes and fees
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
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
$144 nightly
The price is $155 total per night
$155 total
Jun 2 - Jun 3
Total with taxes and fees
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
$263 nightly
The price is $294 total per night
$294 total
Jun 10 - Jun 11
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$141 nightly
The price is $158 total per night
$158 total
Jun 23 - Jun 24
Total with taxes and fees
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 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
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

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $155 nightly
    The price is $173 total per night from Jun 2 to Jun 3
    $173 total
    Jun 2 - Jun 3
    Total with taxes and fees
    9/10 Wonderful! (960 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $145 nightly
    The price is $162 total per night from Jun 2 to Jun 3
    $162 total
    Jun 2 - Jun 3
    Total with taxes and fees
    8.8/10 Excellent! (2,388 reviews)
    Berkshires Untold

    Berkshires Untold

    194 Pittsfield Rd Lenox MA
    $119 nightly
    The price is $133 total per night from Jun 2 to Jun 3
    $133 total
    Jun 2 - Jun 3
    Total with taxes and fees
    9/10 Wonderful! (967 reviews)

Cheshire Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$127
Highest Price
$294
Popular accommodation
The Central Downtown Inn & Suites, The Revival House, Blooming Inn, Berkshire Village Carriage House - Super Private!!, In town, newly remodeled studio with private balcony , The Dewey, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge

More to Explore