Airbnb, Vacation Rentals in Pittsfield, MA

Compare 1,348 available, short term lakefront holiday vacation home properties, starts from $25

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ACCOMMODATION TYPES

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Airbnb, Vacation rentals and hotel deals in Pittsfield, MA

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
$155 /night
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Stay Berkshires
Stay Berkshires
Stay Berkshires
Stay Berkshires
8.4 (330 reviews)
Stay Berkshires
Hotel · 2 Guests · 1 Bedroom
$160 /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
$165 /night
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Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
9.2 (230 reviews)
Hilton Garden Inn Lenox Pittsfield
Hotel · 2 Guests · 1 Bedroom
$213 /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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Life House, Berkshires
Life House, Berkshires
Life House, Berkshires
Life House, Berkshires
8.8 (125 reviews)
Life House, Berkshires
Hotel · 2 Guests · 1 Bedroom
$175 /night
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Quality Inn
Quality Inn
Quality Inn
Quality Inn
Quality Inn
Hotel · 2 Guests · 1 Bedroom
$94 /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
$184 /night*
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Hotel on North
Hotel on North
Hotel on North
Hotel on North
9.4 (187 reviews)
Hotel on North
Hotel · 2 Guests · 1 Bedroom
$198 /night
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Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
9.2 (48 reviews)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Condo · 2 Guests · 1 Bedroom
$258 /night*
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Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
9.2 (31 reviews)
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Condo · 2 Guests · 1 Bedroom
$258 /night*
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Two Rooms with En-Suite in Quiet Woodland
Two Rooms with En-Suite in Quiet Woodland
Two Rooms with En-Suite in Quiet Woodland
Two Rooms with En-Suite in Quiet Woodland
10 (21 reviews)
Two Rooms with En-Suite in Quiet Woodland
Apartment · 2 Guests · 1 Bedroom
$215 /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
$224 /night
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A simple kind of paradise
A simple kind of paradise
A simple kind of paradise
A simple kind of paradise
10 (12 reviews)
A simple kind of paradise
Agritourism · 2 Guests · 1 Bedroom
$195 /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
$127 /night
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The Blue Jay - a New England Cottage
The Blue Jay - a New England Cottage
The Blue Jay - a New England Cottage
The Blue Jay - a New England Cottage
9.6 (5 reviews)
The Blue Jay - a New England Cottage
Cottage · 2 Guests · 1 Bedroom
$200 /night*
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The Red Lion Inn
The Red Lion Inn
The Red Lion Inn
The Red Lion Inn
8.5 (290 reviews)
The Red Lion Inn
Hotel · 2 Guests · 1 Bedroom
$188 /night
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
9.8 (136 reviews)
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Holiday home · 2 Guests · 1 Bedroom
$235 /night*
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Berkshire Inn
Berkshire Inn
Berkshire Inn
Berkshire Inn
7.8 (217 reviews)
Berkshire Inn
Motel · 2 Guests · 1 Bedroom
$78 /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
$69 /night
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Vacation Destinations Near Pittsfield, MA

Airbnb, Holiday Lakefront House with Air Conditioning in Pittsfield, MA

Brook Farm Inn
Brook Farm Inn
Brook Farm Inn
Brook Farm Inn
Air Conditioning
Brook Farm Inn
B & B · 2 Guests · 1 Bedroom
$334 /night
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Chambery Inn
Chambery Inn
Chambery Inn
Chambery Inn
Air Conditioning
9.4 (104 reviews)
Chambery Inn
B & B · 2 Guests · 1 Bedroom
$216 /night
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The Dewey
The Dewey
The Dewey
The Dewey
Air Conditioning
9.1 (63 reviews)
The Dewey
B & B · 2 Guests · 1 Bedroom
$130 /night
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How Does The Amenity Info Looks Like at Pittsfield, MA?
Top Rental Amenities in Pittsfield, MA
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The above reveals the top rental amenities and the property numbers associated with each of them in Pittsfield. In Pittsfield, 635 rentals offer Internet or Wifi, 597 rentals offer No Smoking, 581 rentals offer Parking Available. 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 Kitchen, Hot Tub.
Which Price Range Is Considered As A Good Deal in Pittsfield, MA Area?
Vacation House & Apartment Rental Price Information in Pittsfield, MA
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The graph shows the percentages of vacation homes in each price bucket. Pittsfield has the largest percentage (14.80%) of homes in $150 - $200 price range.
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$500 +
$500 +
What Are The Popular Property Types in Pittsfield, MA?
Most Picked Accommodations in Pittsfield, MA
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Before visiting Pittsfield, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Apartment, Condo, Cottage, Studio, Resort, Cabin, Estate, Farmhouse, Chalet, Chateau / Country House, Lodge, Villa, Barn, Building, Guest House, Townhome, Hotel Suites, Hotel, Mill, Bungalow. House is the most-liked rental type, with the largest percentage of 54.90%. The biggest home in this area available for rent is around 12000 square feet.The least popular accommodation in Pittsfield is Bungalow rentals
How Many Rental Accommodations Are Pets Friendly in Pittsfield, MA?
Pets Allowed vs Not Allowed in Pittsfield, MA
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29.08% of vacation homes in Pittsfield are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Best Tourist Attractions in Pittsfield, MA?
Must Visit Places In Pittsfield, MA
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Where Are The Good Trails in Pittsfield, MA?
Must Visit Trails In Pittsfield, MA
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The most visited trails here in Pittsfield are: Hancock Shaker Village Trail, Ashuwillticook Rail Trail, Appalachian Trail: Dalton to Cheshire, The Boulders, Pittsfield State Forest Area Trails, Turner Trail, Canoe Meadows Wildlife Sanctuary Trail, Brickhouse Mountain Trail, Aspinwall Loop Trail, Pleasant Valley Sanctuary Trail.
Any RV Campgrounds in Pittsfield, MA?
Top Rated Campgrounds In Pittsfield, MA
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The best RV campgrounds here in Pittsfield are: Alps Family Campground, Broken Wheel Campground, Aqua Vista Campground, Woodland Hills Campground, Pine Hollow Campground, Clarksburg Campground, Prospect Lake Park Campground, Tolland State Forest Campground, Northampton / Springfield KOA, Mohawk Trail State Forest Campground.

Other Vacation Rentals Ideas

Airbnb, Holiday Lakefront House with Fireplace in Pittsfield, MA

Richmond Pond Beauty
Richmond Pond Beauty
Richmond Pond Beauty
Richmond Pond Beauty
Fireplace
9.6 (32 reviews)
Richmond Pond Beauty
Holiday home · 2 Guests · 1 Bedroom
$399 /night*
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Rustic Inn in the Shaker Tradition
Rustic Inn in the Shaker Tradition
Rustic Inn in the Shaker Tradition
Rustic Inn in the Shaker Tradition
Fireplace
Rustic Inn in the Shaker Tradition
Guest house · 2 Guests · 1 Bedroom
$828 /night*
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
Fireplace
9.6 (22 reviews)
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
Holiday home · 2 Guests · 1 Bedroom
$984 /night*
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Airbnb, Vacation Condo with Pool in Pittsfield, MA

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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Airbnb, Vacation Condo with Full Kitchen, and Other Rental Options in Pittsfield, MA

Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Full Kitchen
9.2 (48 reviews)
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Condo · 2 Guests · 1 Bedroom
$258 /night*
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2 bedroom Riverhouse in the Heart of the Berkshires
2 bedroom Riverhouse in the Heart of the Berkshires
2 bedroom Riverhouse in the Heart of the Berkshires
2 bedroom Riverhouse in the Heart of the Berkshires
Full Kitchen
9.8 (51 reviews)
2 bedroom Riverhouse in the Heart of the Berkshires
Apartment · 2 Guests · 1 Bedroom
$175 /night*
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New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
Full Kitchen
10 (10 reviews)
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
Apartment · 2 Guests · 1 Bedroom
$270 /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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