Waterfront vacation rentals in Pittsfield
Find and book unique waterfront accommodations on Airbnb
Top-rated waterfront accommodations in Pittsfield
Guests agree: these waterfront accommodations 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
4.88 out of 5 average rating, 279 reviewsGlobetrotter Retreat - Minutes to the Mountain
Oct. 11 – 18
Apartment in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
Feb. 14 – 21
Apartment in Charlemont
5.0 out of 5 average rating, 128 reviewsSuite 23 - Spacious Sunny 2-BR with Mountain view
Feb. 12 – 19
Apartment in Kingston
4.95 out of 5 average rating, 147 reviewsCozy 1 bedroom apartment in the Rondout Kingston
Sep. 24 – Oct. 1
Apartment in Valatie
4.94 out of 5 average rating, 164 reviewsHolland House: Modern Rustic Guest Apartment
Aug. 13 – 20
Apartment in West Granby
4.89 out of 5 average rating, 116 reviewsMajestic Farmhouse Private & Peaceful Guest Apt.
Mar. 6 – 13
Apartment in Wilmington
4.98 out of 5 average rating, 435 reviews**Happy Hour! Gorgeous & Modern Downtown Retreat**
Aug. 20 – 27
Apartment in Saugerties
4.91 out of 5 average rating, 171 reviewsEsopus Bend Getaway - 4 min to HITS
Oct. 6 – 13
Waterfront house rentals
Home in Averill Park
4.95 out of 5 average rating, 143 reviewsCozy, peaceful lake house close to Jiminy Peak
May 28 – Jun. 4
Home in Hillsdale
4.93 out of 5 average rating, 209 reviewsLake House, Copake Lake, NY
Jun. 24 – 29
Home in Hudson
4.96 out of 5 average rating, 339 reviewsRushing Rapids Cottage – a birdwatcher's paradise
Feb. 8 – 15
Home in Great Barrington
4.96 out of 5 average rating, 139 reviewsElegant Year-Round Lakeside Retreat with AC
Apr. 18 – 25
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Dec. 4 – 11
Home in Chatham
4.88 out of 5 average rating, 137 reviewsCountry house on Indian Creek
Sep. 5 – 12
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
Nov. 12 – 19
Home in Saugerties
4.99 out of 5 average rating, 142 reviewsThe Wood House
Feb. 15 – 22
Waterfront condo rentals
Condo in Shelburne Falls
4.88 out of 5 average rating, 32 reviewsFlowers & Falls Spot House
Dec. 14 – 21
Condo in Saratoga Springs
4.95 out of 5 average rating, 22 reviewsLakefront, dock, walk to marina and restaurants!
Mar. 3 – 10
Condo in Saratoga Springs
4.8 out of 5 average rating, 61 reviewsLAKEFRONT: Walk to Marina, Restaurants, Near Track
Jan. 30 – Feb. 6
Condo in Saratoga Springs
4.81 out of 5 average rating, 37 reviewsGorgeous Waterfront - Close to track & Saratoga
May 17 – 24
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
$137 CAD before taxes and fees
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