
Waterfront holiday rentals in Pittsfield
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Pittsfield
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield waterfront rentals
Waterfront apartment accommodation

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!

Sunny Peaceful Home
I highly recommend this airbnb. It was spacious, lovely, and well stocked. Jenny has thought of everything anyone could possibly need while away from home. I don't think I've ever stayed anywhere so well appointed. In addition, the space was beautifully set up, peaceful and quiet. Thank you so much for a lovely stay!

Globetrotter Retreat too - Minutes to the Mountain
Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

River View apartment
If you are in the Brattleboro area, I highly recommend this listing. It was clean, comfortable, and quiet. We were there for just one night, but were very pleased with these accomodations.

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.

Majestic Farmhouse Private & Peaceful Guest Apt.
This was a quick trip to the area to break up the drive to a further destination. Joy's little 18thc apartment was perfect. Joy met and explained everything needed, and was very helpful with local suggestions for dining and activities.Was'nt here long enough to experience any of the hiking trails,.etc but truly seems like a place I'd like to return. if you're lucky, you will meet the inimitable Baloo!
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.

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok
The best Airbnb we’ve ever stayed at! It truly felt like home—every detail was so thoughtfully taken care of. You have everything you need for a comfortable stay, from a well-stocked space to those little touches that make a big difference. The bed and pillows were super comfortable, and even though it rained, the hosts had dry firewood ready for the fireplace, which made it feel extra warm and inviting. We loved sitting by the lake and even saw a fish jump out of the water—such a magical moment! Communication with the host was excellent from start to finish. And thank you so much for approving our cats to stay with us—it meant the world. If we could give 10 stars, we absolutely would. Highly recommend this place to anyone looking for a peaceful and welcoming getaway. Thank you for an unforgettable stay!

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!

Cabin With a Beautiful Lake View
We stayed at Caroline and Nathaniel’s beautiful home over the winter and celebrated NYE’s. Their house is beautiful and perched on top of the hills overlooking a lake. The view is absolutely stunning in the mornings. The house was well maintained and clean. The hosts were very active in communicating with us where we needed anything or if we needed to be aware of any situations regarding the house. I would definitely stay here again.

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 great time, the location is great, right on the water and the fishing was even better. A very quiet lake and much bigger when you are out on it in the kayaks. I would surely stay here again!

Summer 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,
We had a wonderful stay at this peaceful and comfortable lake house. The setting was serene—perfect for a relaxing getaway—and the home itself was clean, cozy, and well-equipped. The owner was incredibly helpful and responsive, always quick to reply to any questions via text, which made the whole experience smooth and stress-free. Highly recommend!
Waterfront condo accommodation

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

Tranquil Lakeside Escape in the Berkshires
Beautiful property. We enjoyed very much the tranquility. There was an issue with the kitchen light but maintenance was going to address it. The exterior of some of the buildings needs to be worked on, but overall the place was great.

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
$165 NZD 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
Wi-Fi availability
20 properties include access to Wi-Fi
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- Long Island Holiday rentals
- The Hamptons Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Montreal Holiday rentals
- South Jersey Holiday rentals
- Rentals with pools Pittsfield
- Kid-friendly rentals Pittsfield
- Rentals with outdoor seating Pittsfield
- Rentals with a hot tub Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with a washing machine and dryer Pittsfield
- Pet-friendly rentals Pittsfield
- Fitness-friendly rentals Pittsfield
- Rentals with lake access Pittsfield
- House rentals Pittsfield
- Rentals with a fireplace Pittsfield
- Rentals with a patio Pittsfield
- Apartment rentals Pittsfield
- Family-friendly rentals Pittsfield
- Waterfront rentals Berkshire County
- Waterfront rentals Massachusetts
- Waterfront rentals 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
- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Opus 40
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards