Waterfront holiday rentals in Pittsfield

Find and book unique waterfront rentals on Airbnb

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Popular amenities for waterfront rentals in Pittsfield

Waterfront apartment rentals

Guest favourite
Flat in Valatie
4.95 out of 5 average rating, 192 reviews

Holland House: Modern Rustic Guest Apartment

AbbieRating, 5 stars1 day ago
This place exceeded our expectations in every way. The highlight was definitely the porch – we spent hours there listening to the birds singing and the gentle sound of the creek. It’s incredibly peaceful and restorative. The space itself is beautifully designed with clean Scandinavian aesthetics that feel both modern and cozy. Everything was immaculately clean, and we loved the thoughtful touches like the small collection of books that made it feel like a home away from home. The location is perfect for nature lovers. There’s a short walk to a creekside trail that’s accessible for all fitness levels – we enjoyed it multiple times during our stay. Our host provided excellent local recommendations that really enhanced our visit. Having the diner downstairs was such a convenience and made our mornings effortless. Great food and no need to venture far for a delicious breakfast. Our host was responsive and clearly cares about providing a top-notch experience.
Top guest favourite
Flat in Charlemont
4.99 out of 5 average rating, 158 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars2 months ago
We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!
Guest favourite
Flat in Shelburne Falls
4.97 out of 5 average rating, 122 reviews

River View Apt in Shelburne Falls Historic Village

JuliaRating, 5 stars3 weeks ago
shelburne Falls is an adorable town, and this Airbnb has a small table with 3 chairs on a back porch that looks out on the river and bridge— very nice . Cute apartment over the the owner’s store and perfect location to walk around town . crystal was a great host…. proactive before our arrival responsive
Top guest favourite
Flat in Newfane
4.97 out of 5 average rating, 454 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars2 days ago
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Top guest favourite
Flat in Kingston
4.96 out of 5 average rating, 238 reviews

DeMew Townhouse in Historic Kingston

LauraRating, 5 stars1 week ago
Such a fantastic stay right in the heart of Kingston! This apartment was exactly as described and incredibly clean. Easy to get to everything in and around Kingston. Tara was a responsive host with clear instructions on how to check in/check out.
Guest favourite
Flat in Craryville
4.92 out of 5 average rating, 137 reviews

Captain's Quarters at Mickey's Marina

CarlRating, 5 stars5 days ago
We had a great say. Beautiful area. Tremendous lake which we enjoyed by kayak. Rooms were clean and comfortable. Nice sitting area outside and another on the front porch. We were here early June and so the eatery next store and another up the road were not open for the season quite yet. Great communication.
Superhost
Flat in Downtown Albany
4.81 out of 5 average rating, 113 reviews

Classic & Homey 2BD/1BA Fl 2 Apt @ Downtown Albany

EdwardRating, 5 stars4 weeks ago
Very clean, comfortable & affordable. Will def stay again!
Guest favourite
Flat in Kingston
4.95 out of 5 average rating, 210 reviews

Cozy 1 bedroom apartment in the Rondout Kingston

AdriaRating, 5 stars4 weeks ago
Clean, great location. Perfect for a weekend visit.

Waterfront house rentals

Top guest favourite
Home in Canaan
4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars4 days ago
This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.
Guest favourite
Home in Saugerties
4.92 out of 5 average rating, 153 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

KateRating, 5 stars3 weeks ago
A great spot close to many fun activities and nature preserves. Friendly hosts and well kept house. Definitely recommend.
Guest favourite
Home in Becket
4.94 out of 5 average rating, 149 reviews

Lake front retreat - Stylish Berkshire home

NitzanRating, 5 stars1 month ago
A true gem! Great location for a Berkshires excursion. Spent two nights, 4 adults and 2 kids. Everything exactly as described. Cute house with everything you may want and need. Loved the design touches. Peaceful and serene, modern and comfortable. Highly recommended!
Guest favourite
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars2 weeks ago
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.
Guest favourite
Home in Copake
4.96 out of 5 average rating, 194 reviews

Lakefront +pets +skiing +bbq +firepit +games

MelanieRating, 5 stars1 month ago
We had a wonderfully relaxing stay at Frank’s beautiful home! The house was spotless, well-equipped, and had everything we could have needed for a comfortable visit. We especially enjoyed the easy access to the lake and the close proximity to great hiking trails. It was the perfect spot to unwind and connect with nature. We would love to come back again soon!
Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Family Fun at Hygge House on Richmond Pond

KatrinaRating, 5 stars8 months ago
The Hygge House was a lovely spot to spend my birthday weekend with my family and friends. We took advantage of so many close-by activities. But the highlights were at the house itself - paddling the canoe and kayak through the water, outdoor dinner, and s’mores at the fire pit. Jessica was also so easy to communicate with and super accommodating during a personal emergency we experienced. We loved our stay and would love to come back again soon.
Top guest favourite
Home in Otis
4.95 out of 5 average rating, 162 reviews

Idyllic family retreat - spacious lake home,

JoelRating, 5 stars4 weeks ago
What an amazing location, and the host was so helpful, answering all our questions rapidly. Beautiful lake home!
Top guest favourite
Home in Averill Park
4.96 out of 5 average rating, 161 reviews

Cozy, peaceful lake house close to Jiminy Peak

PoornaRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay at this beautiful lake house. The interior was warm and inviting, adorned with charming art pieces, while the exterior offered breathtaking views of the lake, lush trees, and open sky. From every room in the house, we could marvel at the serene scenery and spot wildlife, including birds and squirrels. Spending time by the dock and taking a refreshing dip in the lake were highlights of our visit. Whether it was sunny or rainy, this home provided the perfect setting for relaxation. Phyllis was incredibly responsive and her detailed instructions made the pre-check, check-in, and check-out processes seamless. We can’t wait to return!

Waterfront apartment rentals

Superhost
Apartment in Lenox
4.63 out of 5 average rating, 8 reviews

Peaceful 1BR Condo with Pond View

VeraRating, 5 stars5 months ago
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts
Superhost
Apartment in Shelburne Falls
4.92 out of 5 average rating, 48 reviews

Flowers & Falls Spot House

TerriRating, 5 stars1 week ago
Always an easy peaceful stay whenever we stay at David’s place. We will be back again
Guest favourite
Apartment in Saratoga Springs
4.84 out of 5 average rating, 44 reviews

Gorgeous Waterfront - Close to track & Saratoga

RyanRating, 5 stars3 months ago
Nicholas was a great host and the place was awesome! Super clean and has everything you need. My dogs really liked looking out the big windows to the lake :)
Guest favourite
Apartment in Saratoga Springs
4.81 out of 5 average rating, 70 reviews

LAKEFRONT: Walk to Marina, Restaurants, Near Track

SylvanaRating, 5 stars2 weeks ago
This beautiful lake house made this day truly special, despite the cloudy and rainy weather. The house’s warm and welcoming atmosphere was therapeutic, and the lake view was simply breathtaking. Everything we needed was within reach, and Nick was incredibly attentive to our every need.
Guest favourite
Apartment in Saratoga Springs
4.97 out of 5 average rating, 32 reviews

Lakefront, Dock, Near Browns Beach & Restaurants!

KathleenRating, 5 stars2 months ago
Nicholas was very responsive and accommodating. Beautiful place and well maintained.

Quick stats about waterfront rentals in Pittsfield

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹8,572 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

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