
Waterfront vacation rentals in Pittsfield
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Pittsfield
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield waterfront rentals
Waterfront apartment rentals

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Suite 23 - Spacious Sunny 2-BR with Mountain view

Sunny Peaceful Home

Holland House: Modern Rustic Guest Apartment

Globetrotter Retreat too - Minutes to the Mountain

River View Apt in Shelburne Falls Historic Village

Rock River Retreat: VT Oasis Pet Friendly

Majestic Farmhouse Private & Peaceful Guest Apt.
Waterfront house rentals

Lake House in Averill Park, NY (age 30+ excl kids)

Escape to Lakefront Leisure—Amazing views!

Private lakefront home, hot tub & resort amenities

Upstate Waterfront Saugerties Retreat-Near HITS

Lakefront +pets +skiing +bbq +firepit +games

Twin Island Lake House • Hot Tub

Upstate Riverfront Getaway with Hot tub

Direct Lakefront Home on Otis Reservoir Giant Yard
Waterfront condo rentals

Peaceful 1BR Condo with Pond View

Flowers & Falls Spot House

Tranquil Lakeside Escape in the Berkshires

Gorgeous Waterfront - Close to track & Saratoga

LAKEFRONT: Walk to Marina, Restaurants, Near Track

Lakefront, dock, walk to marina and restaurants!
Quick stats about waterfront rentals in Pittsfield
Total rentals
20 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
870 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
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- Stratton Mountain
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- Six Flags New England
- Catamount Mountain Ski Resort
- Albany Center Gallery
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Mount Snow Ski Resort
- Berkshire East Mountain Resort
- Taconic State Park
- Zoom Flume
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- Bright Nights at Forest Park
- Hancock Shaker Village
- Kent Falls State Park
- Beartown State Forest
- Pineridge Cross Country Ski Area
- Naumkeag
- Otis Ridge
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes