Airbnb, Vacation Rentals in Cheshire, MA

Compare 908 available lakefront holiday vacation home properties, starts from $24

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Airbnb, Vacation rentals and hotel deals in Cheshire, MA

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

Airbnb, Holiday Lakefront House with Fireplace in Cheshire, MA

Hudson River Valley/Berkshires Rural Retreat
Hudson River Valley/Berkshires Rural Retreat
Hudson River Valley/Berkshires Rural Retreat
Hudson River Valley/Berkshires Rural Retreat
Fireplace
9.8 (32 reviews)
Hudson River Valley/Berkshires Rural Retreat
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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Enchanting Modern Farmhouse with Picturesque Views
Enchanting Modern Farmhouse with Picturesque Views
Enchanting Modern Farmhouse with Picturesque Views
Enchanting Modern Farmhouse with Picturesque Views
Fireplace
10 (5 reviews)
Enchanting Modern Farmhouse with Picturesque Views
Holiday home · 2 Guests · 1 Bedroom
$367 /night*
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Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond
Froggy Pond - Family-Friendly Home With Incredible Views And A Private Swim Pond
Fireplace
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!
Spacious Historic Home in the Berkshires!
Spacious Historic Home in the Berkshires!
Spacious Historic Home in the Berkshires!
Full Kitchen
Spacious Historic Home in the Berkshires!
Holiday home · 2 Guests · 1 Bedroom
$292 /night*
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Hudson River Valley/Berkshires Rural Retreat
Hudson River Valley/Berkshires Rural Retreat
Hudson River Valley/Berkshires Rural Retreat
Hudson River Valley/Berkshires Rural Retreat
Full Kitchen
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!
Bennington Cabin w/ Deck & Views of 3 States!
Bennington Cabin w/ Deck & Views of 3 States!
Bennington Cabin w/ Deck & Views of 3 States!
Full Kitchen
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

FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
Pool
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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Wyndham Bentley Brook Condo Resort
Wyndham Bentley Brook Condo Resort
Wyndham Bentley Brook Condo Resort
Wyndham Bentley Brook Condo Resort
Pool
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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