Compare Cheshire Guest House Rentals

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Featured Guest Houses in Cheshire

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 26 - Jul 27
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.
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$104 nightly
The price is $116 total per night
$116 total
Jul 23 - Jul 24
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
Jul 27 - Jul 28
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
$152 nightly
The price is $164 total per night
$164 total
Aug 18 - Aug 19
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.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$239 nightly
The price is $267 total per night
$267 total
Jul 28 - Jul 29
Total with taxes and fees
Guests staying at this guesthouse have access to a garden and barbecue grills.
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls MA
$191 nightly
The price is $213 total per night
$213 total
Jul 26 - Jul 27
Total with taxes and fees
This guesthouse features free WiFi in public areas and a garden.
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
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.
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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
    $145 nightly
    The price is $162 total per night from Jul 23 to Jul 24
    $162 total
    Jul 23 - Jul 24
    Total with taxes and fees
    8.8/10 Excellent! (2,464 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $161 nightly
    The price is $179 total per night from Aug 16 to Aug 17
    $179 total
    Aug 16 - Aug 17
    Total with taxes and fees
    8.8/10 Excellent! (1,000 reviews)
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $189 nightly
    The price is $211 total per night from Jul 23 to Jul 24
    $211 total
    Jul 23 - Jul 24
    Total with taxes and fees

Cheshire Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$116
Highest Price
$267
Popular accommodation
Hideaway Inn Lenox, 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, Cliffwood Cottage by Evergreen Home, Jacob's Tanglewood Ranch

More to Explore