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
Apartment in Wilmington
4.91 out of 5 average rating, 109 reviewsGlobetrotter Retreat too - Minutes to the Mountain
Apr 28 – May 5
Apartment in Schenectady
4.9 out of 5 average rating, 177 reviewsBring your Kayak or paddleboard this Summer!
Dec 11 – 18
Apartment in Valatie
4.94 out of 5 average rating, 164 reviewsHolland House: Modern Rustic Guest Apartment
Oct 24 – 31
Apartment in Charlemont
5.0 out of 5 average rating, 128 reviewsSuite 23 - Spacious Sunny 2-BR with Mountain view
Oct 4 – 11
Apartment in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
Dec 1 – 8
Apartment in Wilmington
4.98 out of 5 average rating, 438 reviews**Happy Hour! Gorgeous & Modern Downtown Retreat**
Jun 10 – 17
Apartment in Kingston
4.95 out of 5 average rating, 150 reviewsCozy 1 bedroom apartment in the Rondout Kingston
Oct 22 – 29
Apartment in West Granby
4.89 out of 5 average rating, 116 reviewsMajestic Farmhouse Private & Peaceful Guest Apt.
Apr 15 – 22
Waterfront house rentals
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Mar 23 – 30
Home in Hudson
4.96 out of 5 average rating, 340 reviewsRushing Rapids Cottage – a birdwatcher's paradise
Oct 17 – 24
Home in Averill Park
4.95 out of 5 average rating, 143 reviewsCozy, peaceful lake house close to Jiminy Peak
May 29 – Jun 5
Home in Great Barrington
4.96 out of 5 average rating, 140 reviewsElegant Year-Round Lakeside Retreat with AC
Nov 17 – 24
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Jan 27 – Feb 3
Home in Chatham
4.88 out of 5 average rating, 138 reviewsCountry house on Indian Creek
Oct 21 – 28
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
Feb 20 – 27
Home in Saugerties
4.99 out of 5 average rating, 144 reviewsThe Wood House
Apr 16 – 23
Waterfront condo rentals
Condo in Shelburne Falls
4.88 out of 5 average rating, 33 reviewsFlowers & Falls Spot House
Jun 10 – 17
Condo in Saratoga Springs
4.95 out of 5 average rating, 22 reviewsLakefront, dock, walk to marina and restaurants!
Dec 25 – Jan 1
Condo in Saratoga Springs
4.8 out of 5 average rating, 61 reviewsLAKEFRONT: Walk to Marina, Restaurants, Near Track
May 23 – 30
Condo in Saratoga Springs
4.81 out of 5 average rating, 37 reviewsGorgeous Waterfront - Close to track & Saratoga
Nov 27 – Dec 4
Quick stats about waterfront rentals in Pittsfield
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
730 reviews
Nightly prices starting at
$100 before taxes and fees
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