Cheshire hotels

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Best Cheshire hotels

Discover the best hotels in Cheshire and compare prices, ratings, and locations to find the right stay for your trip.
These are the best prices for Sep 28 - 29.
Harbour House Inn - Cheshire
Harbour House Inn - Cheshire
Harbour House Inn
Cheshire, MA
9.6Wonderful(29)
Parking
Free Wi-Fi
$245+
Check availability
The Trail in Adams - Berkshires' Art Hotel - Adams - Living room
The Trail in Adams - Berkshires' Art Hotel - Adams - Living room
The Trail in Adams - Berkshires' Art Hotel
Adams, MA
8.5Very good(60)
Parking
Free Wi-Fi
$204+
Check availability
Berkshire Valley Inn - New Ashford - Living room
Berkshire Valley Inn - New Ashford - Living room
Berkshire Valley Inn
New Ashford, MA
9.3Wonderful(108)
Parking
Free Wi-Fi
Pool
Pet friendly
$189+
Check availability
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities! - Lanesborough - Building
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities! - Lanesborough - Building
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!
Lanesborough, MA
9.2Wonderful(15)
$212+
Check availability
Berkshire Hills Nature Lovers' Log Home Retreat - Cheshire - Living room
Berkshire Hills Nature Lovers' Log Home Retreat - Cheshire - Living room
Berkshire Hills Nature Lovers' Log Home Retreat
Cheshire, MA
9.7Wonderful(4)
House
Parking
Free Wi-Fi
Pet friendly
$635+
Check availability
19th c. Barn in the Berkshires - Cheshire - Living room
19th c. Barn in the Berkshires - Cheshire - Living room
19th c. Barn in the Berkshires
Cheshire, MA
9.4Wonderful(32)
House
Free Wi-Fi
$506+
Check availability
Berkshires Lakefront Retreat by Evergreen Home - Cheshire - Patio
Berkshires Lakefront Retreat by Evergreen Home - Cheshire - Patio
Berkshires Lakefront Retreat by Evergreen Home
Cheshire, MA
9.8Wonderful(11)
House
Free Wi-Fi
$839+
Check availability
Private Mountain Retreat On 10 Acres The Perfect Family Escape - Cheshire
Private Mountain Retreat On 10 Acres The Perfect Family Escape - Cheshire
Private Mountain Retreat On 10 Acres The Perfect Family Escape
Cheshire, MA
10Wonderful(1)
House
Parking
$776+
Check availability

Hotel deals for next week

Some of KAYAK users’ favorite hotels with availability next week Sep 28 - 29.
Cabin Rental for Four in Stephentown, New York, for Weekend Getaways to Nature - Cheshire - Outdoors view
Cabin Rental for Four in Stephentown, New York, for Weekend Getaways to Nature
Cheshire, MA
5.1Fair(9)
Cabin
$157+
Check availability
Cheshire Cove | Waterfront • Kayak • Firepit - Cheshire - Living room
Cheshire Cove | Waterfront • Kayak • Firepit
Cheshire, MA
House
Free Wi-Fi
$509+
Check availability
Renovated Historic Berkshire Gem w/Hot Tub • Pool - Cheshire - Living room
Renovated Historic Berkshire Gem w/Hot Tub • Pool
Cheshire, MA
House
$1,210+
Check availability

Top-rated hotels

Stay at the hotels that our users loved the most Sep 28 - 29.
Berkshires Lakefront Retreat by Evergreen Home - Cheshire - Patio
Berkshires Lakefront Retreat by Evergreen Home
Cheshire, MA
9.8Wonderful(11)
House
Free Wi-Fi
$839+
Check availability
Harbour House Inn - Cheshire
Harbour House Inn
Cheshire, MA
9.6Wonderful(29)
Parking
Free Wi-Fi
$245+
Check availability
19th c. Barn in the Berkshires - Cheshire - Living room
19th c. Barn in the Berkshires
Cheshire, MA
9.4Wonderful(32)
House
Free Wi-Fi
$506+
Check availability
Berkshire Valley Inn - New Ashford - Living room
Berkshire Valley Inn
New Ashford, MA
9.3Wonderful(108)
Parking
Free Wi-Fi
Pool
Pet friendly
$189+
Check availability
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities! - Lanesborough - Building
Comfy Suite in the Berkshires w/ WiFi & Great Resort Amenities!
Lanesborough, MA
9.2Wonderful(15)
$212+
Check availability
The Trail in Adams - Berkshires' Art Hotel - Adams - Living room
The Trail in Adams - Berkshires' Art Hotel
Adams, MA
8.5Very good(60)
Parking
Free Wi-Fi
$204+
Check availability

Popular filters in Cheshire hotels

Hotels with parking
Harbour House Inn, The Trail in Adams - Berkshires' Art Hotel and others
Find stays
Hotels with free cancellation
Explore hotel deals with free cancellation in the area
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Useful Info

Good to know

Low season

High season

Average price (weekend night)

September
July
$349
Cheapest month to stay with an average 5% drop in price.
Most expensive month to stay with an average 5% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Cheshire hotel deals

  • If you’re looking for a cheap hotel in Albany, you should consider visiting during the low season. You'll find cheaper accommodations in Albany in September and July.
  • How long should you stay? KAYAK users usually book their accommodation in Albany for 5 days.

FAQs when booking a hotel in Cheshire

  • How do I find a hotel in central Cheshire?

    After you launch a hotel search on KAYAK, you can refine your research by neighborhood, which allows you to pick the central Cheshire districts. You can also do a search using the city map to choose a specific location, like Cheshire city center.

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Cheshire hotels with free parking?

    There are many hotels in Cheshire that offer both parking and free parking. Popular choices among KAYAK users include Harbour House Inn, The Trail in Adams - Berkshires' Art Hotel and Berkshire Valley Inn.

Where to stay in Cheshire?

Our map will help you find the perfect place to stay in Cheshire by showing you the exact location of each hotel.

More options for your stay in Cheshire