Compare Inns in Cheshire

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Featured Inns in Cheshire

Gregory House Country Inn

Gregory House Country Inn

3 out of 5
3016 New York 43 Averill Park NY
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $125 total per night
$125 total
Nov 22 - Nov 23
Total with taxes and fees
Guests staying at Gregory House Country Inn enjoy free WiFi in public areas, a terrace, and a communal living room. Free parking is included with your stay. This inn also has a picnic area.
Parking included
Free WiFi
Apple Tree Inn

Apple Tree Inn

3 out of 5
10 Richmond Mountain Rd Lenox MA
Guests of Apple Tree Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and express check-out. If you drive, put free parking to good use. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include a terrace, a garden, and a picnic area.
Pool
Breakfast included
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 out of 5
910 Cold Spring Road Williamstown MA
$113 nightly
The price is $127 total per night
$127 total
Nov 30 - Dec 1
Total with taxes and fees
1896 House Country Inn & Motels features free WiFi in public areas, conference space, and a business center. Free parking is included with your stay. Staff members are on hand to provide tour or ticket assistance and luggage storage. Additional amenities include a computer station, a terrace, and a garden.
Pet friendly
Parking included
Kemble Inn

Kemble Inn

3.5 out of 5
2 Kemble Street Lenox MA
Guests of Kemble Inn enjoy free WiFi in public areas, a hot tub, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with tours/tickets and luggage storage. Other amenities at this boutique inn include coffee/tea in a common area, a library, and free newspapers.
Hot Tub
Breakfast included
The Kemble Berkshires

The Kemble Berkshires

2 out of 5
2 Kemble St Lenox MA
Guests staying at The Kemble Berkshires enjoy free WiFi in public areas, a terrace, and a garden. If you decide to drive, there's free parking. This inn also has barbecue grills.
Parking included
Free WiFi
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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

    Harbour House Inn

    Harbour House Inn

    725 North State Road Cheshire MA
    $249 nightly
    The price is $264 total per night from Dec 1 to Dec 2
    $264 total
    Dec 1 - Dec 2
    Total with taxes and fees
    9.6/10 Exceptional! (39 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $94 nightly
    The price is $105 total per night from Nov 23 to Nov 24
    $105 total
    Nov 23 - Nov 24
    Total with taxes and fees
    8.6/10 Excellent! (2,136 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $107 nightly
    The price is $120 total per night from Dec 20 to Dec 21
    $120 total
    Dec 20 - Dec 21
    Total with taxes and fees
    8.6/10 Excellent! (1,004 reviews)

Inns

Find a great Cheshire inn
If you’re on the lookout for a place to stay in Cheshire that sports special touches and décor but is less costly than a bed and breakfast, rent a room at an inn. Whether you’re staying for a day, a week or a month, Orbitz has a great selection of super-comfy Cheshire inns to choose from.

Pick the right inn for you
The most popular hotel inns in Cheshire merge the convenience of an inn with many of the standard features of a hotel. Think pools and gyms, without the hefty price tag.

You’ll find Cheshire inns are located in all sort of convenient neighborhoods, making them a great option for those traveling on four wheels. They can also offer a tasty breakfast and hearty dinner, saving you the time and effort it would take to find good eats in a new place. 

If you want a space filled with loads of personality and a good helping of hospitality to boot, look out for historic inns. Privately owned with an exclusive number of rooms, you’ll receive a more personalized stay, much like a boutique hotel. No matter what type of inn you choose, you’re sure to enjoy unique experiences you won’t find anywhere else.

Cheshire Inns essential information

Accommodation
5 Inns
Lowest Price
$105
Highest Price
$264
Popular accommodation
Gregory House Country Inn, Apple Tree Inn, 1896 House Country Inn & Motels, Kemble Inn, The Kemble Berkshires