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
$94 nightly
The price is $105 total per night
$105 total
Jan 13 - Jan 14
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
Blooming Inn

Blooming Inn

3 out of 5
22 Mechanic St Shelburne Falls MA
$139 nightly
The price is $150 total per night
$150 total
Jan 11 - Jan 12
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
$188 nightly
The price is $210 total per night
$210 total
Jan 9 - Jan 10
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
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
$150 nightly
The price is $168 total per night
$168 total
Jan 11 - Jan 12
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
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
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$140 nightly
The price is $156 total per night
$156 total
Jan 13 - Jan 14
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
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 a picnic area. You can take advantage of free parking if you drive. Additional amenities include a communal living room and barbecue grills.
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
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
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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
    $126 nightly
    The price is $141 total per night from Jan 11 to Jan 12
    $141 total
    Jan 11 - Jan 12
    Total with taxes and fees
    8.6/10 Excellent! (2,200 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $125 nightly
    The price is $140 total per night from Feb 2 to Feb 3
    $140 total
    Feb 2 - Feb 3
    Total with taxes and fees
    8.6/10 Excellent! (1,002 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $98 nightly
    The price is $109 total per night from Jan 9 to Jan 10
    $109 total
    Jan 9 - Jan 10
    Total with taxes and fees
    8/10 Very Good! (1,003 reviews)

Cheshire Guest Houses essential information

Accommodation
9 Guest Houses
Lowest Price
$105
Highest Price
$210
Popular accommodation
The Central Downtown Inn & Suites, Blooming Inn, Berkshire Village Carriage House - Super Private!!, The Revival House, The Dewey, In town, newly remodeled studio with private balcony , Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home

More to Explore