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Airbnb, Vacation rentals and hotel deals in Cheshire, MA

9.8 (55 reviews)
Inn at Silver Maple Farm
B & B · 2 Guests · 1 Bedroom
$126 /night
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8.9 (125 reviews)
Fairfield Inn & Suites by Marriott Williamstown
Hotel · 2 Guests · 1 Bedroom
$179 /night
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9.3 (227 reviews)
Courtyard by Marriott Lenox Berkshires
Hotel · 2 Guests · 1 Bedroom
$219 /night
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6.2 (474 reviews)
Econo Lodge Lee - Great Barrington
Motel · 2 Guests · 1 Bedroom
$63 /night
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The Black Swan Lee - Lenox, Ascend Hotel Collection
Hotel · 2 Guests · 1 Bedroom
$121 /night
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9.1 (350 reviews)
Hampton Inn & Suites Berkshires-Lenox
Hotel · 2 Guests · 1 Bedroom
$155 /night
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6.7 (114 reviews)
Pleasant Valley Motel West Stockbridge
Motel · 2 Guests · 1 Bedroom
$59 /night
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8.6 (220 reviews)
The Central Downtown Inn Suites
Hotel · 2 Guests · 1 Bedroom
$129 /night
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9.8 (32 reviews)
Hudson River Valley/Berkshires Rural Retreat
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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7.4 (18 reviews)
The Constance
B & B · 2 Guests · 1 Bedroom
$162 /night
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9.2 (82 reviews)
Cozy and quaint country cottage, walk to downtown Williamstown
Holiday home · 2 Guests · 1 Bedroom
$142 /night*
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9.1 (148 reviews)
Willows Motel
Motel · 2 Guests · 1 Bedroom
$78 /night
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6.2 (59 reviews)
Pilgrim Inn
Inn · 2 Guests · 1 Bedroom
$76 /night
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10 (2 reviews)
Stockbridge Home: Walk to Town Beach!
Holiday home · 2 Guests · 1 Bedroom
$179 /night*
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8.4 (224 reviews)
Best Western Plus Berkshire Hills Inn & Suites
Hotel · 2 Guests · 1 Bedroom
$132 /night
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8.7 (585 reviews)
Vacation Village in the Berkshires
Holiday park · 2 Guests · 1 Bedroom
$165 /night
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8.9 (212 reviews)
Cozy Corner Motel
Motel · 2 Guests · 1 Bedroom
$78 /night
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8.6 (130 reviews)
Berkshire Mountain Lodge
Lodge · 2 Guests · 1 Bedroom
$178 /night
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7.7 (316 reviews)
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$142 /night
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9.4 (104 reviews)
Chambery Inn
B & B · 2 Guests · 1 Bedroom
$216 /night
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Airbnb, Holiday Lakefront House with Fireplace in Cheshire, MA

9.8 (32 reviews)
Hudson River Valley/Berkshires Rural Retreat
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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10 (5 reviews)
Enchanting Modern Farmhouse with Picturesque Views
Holiday home · 2 Guests · 1 Bedroom
$367 /night*
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9.8 (26 reviews)
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond
Holiday home · 2 Guests · 1 Bedroom
$414 /night*
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What Are The Most Popular Amenities in Cheshire, MA?
Amenity Info in Cheshire, MA
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There are in total of 15 rental amenities in Cheshire, shown above with the property numbers. In Cheshire, 432 rentals offer Internet or Wifi, 393 rentals offer Parking Available, 371 rentals offer No Smoking. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Pets Friendly, Hot Tub.
Which Price Range Is Most Typical in Cheshire, MA Area?
Vacation House & Condo Rental Price Information in Cheshire, MA
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The graph shows the percentages of vacation homes in each price bucket. Cheshire has the largest percentage (17.59%) of homes in $100 - $150 price range.
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Which Accommodations Should I Pick in Cheshire, MA?
Best Accommodation Types in Cheshire, MA
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There are various types of homes in Cheshire area. Depending on your group size, you can pick the one using filters accordingly. House is the most popular accommodation type, and the largest homes can accommodate 38 people.The least popular accommodation in Cheshire is Hotel Suites rentals
How Many Accommodations Are Pets Allowed in Cheshire, MA?
Percentage of Pet Friendly Rental Properties in Cheshire, MA
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24.23% of vacation homes in Cheshire are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Where Are The Good Trails in Cheshire, MA?
Must Visit Trails In Cheshire, MA
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Here are the trails we recommend in Cheshire: Bradley Farm Interpretive Trail, Mount Greylock South Flank and Rounds Rock, Cheshire Cobbles Trail, The Cobbles Via Appalachian Trail, Rounds Rock Trail, Saddle Ball Mountain, Jones Nose Trail, Mount Greylock and Saddle Ball Mountain, Cheshire Harbor Trail to Mount Greylock, March Cataract Falls Trail.
Best Campgrounds in Cheshire, MA?
Most Visited Campgrounds In Cheshire, MA
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For campgrounds in Cheshire, here are our recommendations: Alps Family Campground, Broken Wheel Campground, Aqua Vista Campground, Woodland Hills Campground, Pine Hollow Campground, Clarksburg Campground, Prospect Lake Park Campground, Northampton / Springfield KOA, Mohawk Trail State Forest Campground, Indian Hollow Campground.
Which Airports Should I Choose To Get To Cheshire, MA?
Top Airports in Cheshire, MA
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Here are the airports that located near Cheshire:

Airbnb, Holiday Lakefront House with Full Kitchen, and Other Rental Options in Cheshire, MA

Spacious Historic Home in the Berkshires!
Holiday home · 2 Guests · 1 Bedroom
$292 /night*
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9.8 (32 reviews)
Hudson River Valley/Berkshires Rural Retreat
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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Bennington Cabin w/ Deck & Views of 3 States!
Cottage · 2 Guests · 1 Bedroom
$392 /night
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Airbnb, Vacation Condo with Pool in Cheshire, MA

9.4 (68 reviews)
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
Apartment · 2 Guests · 1 Bedroom
$185 /night*
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9.8 (14 reviews)
Wyndham Bentley Brook Condo Resort
Condo · 2 Guests · 1 Bedroom
$799 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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