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Here at VacationHomeRents, you can easily find and compare the best vacation apartments, cabins, house boats, beach houses, and RV deals. By a simple click, we help you search among millions of listings across the top sites like Airbnb, Vrbo, Booking.com and more.
Airbnb Pittsfield, MAVrbo Pittsfield, MABooking.com Pittsfield, MAOutdoorsy Pittsfield, MARvshare.com Pittsfield, MA
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ACCOMMODATION TYPES

Save Up To 77%

Airbnb, Vacation rentals and hotel deals in Pittsfield, MA

Yankee Suites Extended Stay
4.3 (240 reviews)
Yankee Suites Extended Stay
Guest house · 1 Bedroom
$126 /night
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Hampton Inn & Suites Berkshires-Lenox
4.5 (1543 reviews)
Hampton Inn & Suites Berkshires-Lenox
Hotel · 1 Bedroom
$162 /night
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Howard Johnson by Wyndham Lenox
3.7 (1008 reviews)
Howard Johnson by Wyndham Lenox
Hotel · 1 Bedroom
$69 /night
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
4.6 (51 reviews)
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Holiday home · 6 Guests · 3 Bedrooms
$186 /night*
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Berkshire Yankee Suites - An Extended Stay Hotel
4.3 (26 reviews)
Berkshire Yankee Suites - An Extended Stay Hotel
Hotel · 1 Bedroom
$130 /night
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The Cornell Inn, Lenox
4.6 (409 reviews)
The Cornell Inn, Lenox
B & B · 1 Bedroom
$168 /night
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Wagon Wheel Inn
3.6 (739 reviews)
Wagon Wheel Inn
Motel · 1 Bedroom
$69 /night
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Cozy rustic studio minutes from Jiminy Peak
5.0 (2 reviews)
Cozy rustic studio minutes from Jiminy Peak
Apartment · 2 Guests · 1 Bedroom
$100 /night*
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Yankee Inn
4.3 (1472 reviews)
Yankee Inn
Hotel · 1 Bedroom
$95 /night
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Airbnb, Holiday Lakefront House with Air Conditioning in Pittsfield, MA

Charming historic cottage on scenic road to Mt. Greylock
Air Conditioning
4.9 (151 reviews)
Charming historic cottage on scenic road to Mt. Greylock
Cottage · 4 Guests · 2 Bedrooms
$190 /night*
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Brook Farm Inn
Air Conditioning
2.7 (87 reviews)
Brook Farm Inn
B & B · 1 Bedroom
$321 /night
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Grand Colonial Home in the heart of the Berkshires
Air Conditioning
4.9 (22 reviews)
Grand Colonial Home in the heart of the Berkshires
Holiday home · 10 Guests · 5 Bedrooms
$449 /night*
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Airbnb, Holiday Lakefront House with Fireplace in Pittsfield, MA

Luxury Berkshires Retreat in Lenox - Main House  & Studio
Fireplace
4.9 (11 reviews)
Luxury Berkshires Retreat in Lenox - Main House & Studio
Holiday home · 14 Guests · 7 Bedrooms
$1,150 /night*
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Heart of Lenox Walk to Town Cozy Cottage!
Fireplace
5.0 (29 reviews)
Heart of Lenox Walk to Town Cozy Cottage!
Holiday home · 4 Guests · 2 Bedrooms
$349 /night*
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Enjoy comfortable elegance in this secluded grand home located in Lenox town
Fireplace
5.0 (43 reviews)
Enjoy comfortable elegance in this secluded grand home located in Lenox town
Holiday home · 10 Guests · 5 Bedrooms
$800 /night*
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Airbnb, Vacation Condo with Pool in Pittsfield, MA

Jiminy Peak 4 LEVEL DELUXE SKI CONDO- 3+ BEDROOMS, 2 BATHS, WHIRLPOOL,SAUNA MORE
Pool
3.3 (39 reviews)
Jiminy Peak 4 LEVEL DELUXE SKI CONDO- 3+ BEDROOMS, 2 BATHS, WHIRLPOOL,SAUNA MORE
Condo · 8 Guests · 4 Bedrooms
$500 /night*
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Airbnb, Vacation Condo with Full Kitchen, and Other Rental Options in Pittsfield, MA

Historical  Downtown 1bedroom
Full Kitchen
5.0 (22 reviews)
Historical Downtown 1bedroom
Apartment · 2 Guests · 1 Bedroom
$195 /night*
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Renovated Downtown 1bedroom
Full Kitchen
5.0 (16 reviews)
Renovated Downtown 1bedroom
Apartment · 2 Guests · 1 Bedroom
$195 /night*
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Jiminy Peak 4 LEVEL DELUXE SKI CONDO- 3+ BEDROOMS, 2 BATHS, WHIRLPOOL,SAUNA MORE
Full Kitchen
3.3 (39 reviews)
Jiminy Peak 4 LEVEL DELUXE SKI CONDO- 3+ BEDROOMS, 2 BATHS, WHIRLPOOL,SAUNA MORE
Condo · 8 Guests · 4 Bedrooms
$500 /night*
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How Does The Amenity Info Looks Like at Pittsfield, MA?

Top Rental Amenities in Pittsfield, MA

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

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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How Many Rental Accommodations Are Pets Friendly in Pittsfield, MA?
Pets Allowed vs Not Allowed in Pittsfield, MA
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.
Where Are The Good Trails in Pittsfield, MA?
Must Visit Trails In Pittsfield, MA
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
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.
* 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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