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
$170 nightly
The price is $190 total per night
$190 total
Sep 8 - Sep 9
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 picnic area, and a TV in a common area.
Pet friendly
Parking included
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$99 nightly
The price is $111 total per night
$111 total
Sep 9 - Sep 10
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
Sep 8 - Sep 9
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
$143 nightly
The price is $154 total per night
$154 total
Sep 16 - Sep 17
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
$206 nightly
The price is $230 total per night
$230 total
Sep 16 - Sep 17
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
$140 nightly
The price is $156 total per night
$156 total
Oct 6 - Oct 7
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
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 a fireplace in the lobby. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
Pet friendly
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
    $122 nightly
    The price is $136 total per night from Sep 8 to Sep 9
    $136 total
    Sep 8 - Sep 9
    Total with taxes and fees
    8.8/10 Excellent! (2,611 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $143 nightly
    The price is $160 total per night from Sep 27 to Sep 28
    $160 total
    Sep 27 - Sep 28
    Total with taxes and fees
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $113 nightly
    The price is $126 total per night from Oct 1 to Oct 2
    $126 total
    Oct 1 - Oct 2
    Total with taxes and fees
    9/10 Wonderful! (1,132 reviews)

Cheshire Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$111
Highest Price
$230
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