
Waterfront holiday rentals in Pittsfield
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Top-rated waterfront rentals in Pittsfield
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Popular amenities for waterfront rentals in Pittsfield
Waterfront apartment rentals

Holland House: Modern Rustic Guest Apartment
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.

Suite 23 - Spacious Sunny 2-BR with Mountain view
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!

River View Apt in Shelburne Falls Historic Village
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

Rock River Retreat: VT Oasis Pet Friendly
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.

DeMew Townhouse in Historic Kingston
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.

Captain's Quarters at Mickey's Marina
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.

Classic & Homey 2BD/1BA Fl 2 Apt @ Downtown Albany
Very clean, comfortable & affordable. Will def stay again!

Cozy 1 bedroom apartment in the Rondout Kingston
Clean, great location. Perfect for a weekend visit.
Waterfront house rentals

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

Upstate Waterfront Saugerties Retreat-Near HITS
A great spot close to many fun activities and nature preserves. Friendly hosts and well kept house. Definitely recommend.

Lake front retreat - Stylish Berkshire home
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!

Twin Island Lake House • Hot Tub
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.

Lakefront +pets +skiing +bbq +firepit +games
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!

Family Fun at Hygge House on Richmond Pond
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.

Idyllic family retreat - spacious lake home,
What an amazing location, and the host was so helpful, answering all our questions rapidly. Beautiful lake home!

Cozy, peaceful lake house close to Jiminy Peak
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

Peaceful 1BR Condo with Pond View
Very nice and clean 1-bedroom apartment with a great view and everything you need for cooking meals. Wonderful location and very kind hosts

Flowers & Falls Spot House
Always an easy peaceful stay whenever we stay at David’s place. We will be back again

Gorgeous Waterfront - Close to track & Saratoga
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 :)

LAKEFRONT: Walk to Marina, Restaurants, Near Track
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.

Lakefront, Dock, Near Browns Beach & Restaurants!
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
Destinations to explore
- Hudson Valley Holiday rentals
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- Rentals with pools Pittsfield
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- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- John Boyd Thacher State Park
- Stratton Mountain Resort
- Albany Center Gallery
- Catamount Mountain Ski Resort
- Taconic State Park
- Bash Bish Falls State Park
- Mount Snow Ski Resort
- Zoom Flume
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Kent Falls State Park
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Brignole Vineyards
- Pineridge Cross Country Ski Area
- Beartown State Forest