
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

Lovely 1 bedroom apt. with free parking in Rondout

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

Sunny Peaceful Home

Holland House: Modern Rustic Guest Apartment

Globetrotter Retreat too - Minutes to the Mountain

River View Apt in Shelburne Falls Historic Village

DeMew Townhouse in Historic Kingston

Majestic Farmhouse Private & Peaceful Guest Apt.
Waterfront house rentals

Lakefront close to ski & shopping

Private lakefront home, hot tub & resort amenities

Stylish Waterfront Escape on the Esopus Creek

Twin Island Lake House • Hot Tub

Majestic lake front house

Upstate Riverfront Getaway with Hot tub

Hudson Riverfront Mid-Century Modern Home

Saratoga Lake Access | Private Dock | BEST Views!
Waterfront condo rentals

Gorgeous Waterfront - Close to track & Saratoga

LAKEFRONT: Walk to Marina, Restaurants, Near Track

Lakefront, dock, walk to marina and restaurants!

Flowers & Falls Spot House
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
- Hudson Valley Vacation rentals
- Boston Vacation rentals
- Long Island Vacation rentals
- The Hamptons Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Cape Cod Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Montreal Vacation rentals
- Rentals with a patio Pittsfield
- Apartment rentals Pittsfield
- Rentals with a hot tub Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a washer and dryer Pittsfield
- Kid-friendly rentals Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with outdoor seating Pittsfield
- Pet-friendly rentals Pittsfield
- Fitness-friendly rentals Pittsfield
- House rentals Pittsfield
- Rentals with pools Pittsfield
- Rentals with lake access Pittsfield
- Rentals with a fireplace Pittsfield
- Waterfront rentals Berkshire County
- Waterfront rentals Massachusetts
- Waterfront rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Six Flags New England
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- Zoom Flume
- John Boyd Thacher State Park
- Mohawk Mountain Ski Area
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Opus 40
- Norman Rockwell Museum
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Ekwanok Country Club
- Bright Nights at Forest Park
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- 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