Waterfront holiday rentals in Pittsfield

Find and book unique waterfront accommodation on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Pittsfield waterfront rentals

Waterfront apartment accommodation

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

Holland House: Modern Rustic Guest Apartment

AbbieRating, 5 stars1 week 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
Apartment in Charlemont
4.99 out of 5 average rating, 158 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars3 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!
Top Guest favourite
Apartment in Florence
4.92 out of 5 average rating, 630 reviews

Sunny Peaceful Home

JeanRating, 5 stars2 weeks ago
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!
Guest favourite
Apartment in Wilmington
4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars2 months ago
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.
Top Guest favourite
Apartment in Brattleboro
4.99 out of 5 average rating, 141 reviews

River View apartment

JohnRating, 5 stars2 days ago
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.
Guest favourite
Apartment in Shelburne Falls
4.97 out of 5 average rating, 122 reviews

River View Apt in Shelburne Falls Historic Village

JuliaRating, 5 stars4 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
Apartment in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars1 week 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.
Guest favourite
Apartment in West Granby
4.9 out of 5 average rating, 131 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

CindyRating, 5 stars9 months ago
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

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 stars1 week 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 Ancram
4.99 out of 5 average rating, 181 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

AdelyaRating, 5 stars1 month ago
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!
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!
Superhost
Home in Lee
5 out of 5 average rating, 7 reviews

Cabin With a Beautiful Lake View

HumiraRating, 5 stars5 months ago
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.
Guest favourite
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars3 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, 195 reviews

Lakefront +pets +skiing +bbq +firepit +games

RichRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Summer 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, 163 reviews

Idyllic family retreat - spacious lake home,

MaryRating, 5 stars2 weeks ago
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

Superhost
Condo 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
Condo in Shelburne Falls
4.92 out of 5 average rating, 48 reviews

Flowers & Falls Spot House

TerriRating, 5 stars2 weeks ago
Always an easy peaceful stay whenever we stay at David’s place. We will be back again
Superhost
Condo in Lenox
4.8 out of 5 average rating, 10 reviews

Tranquil Lakeside Escape in the Berkshires

GregoryRating, 5 stars3 weeks ago
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.
Guest favourite
Condo in Saratoga Springs
4.84 out of 5 average rating, 44 reviews

Gorgeous Waterfront - Close to track & Saratoga

RyanRating, 5 stars4 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
Condo in Saratoga Springs
4.81 out of 5 average rating, 70 reviews

LAKEFRONT: Walk to Marina, Restaurants, Near Track

SylvanaRating, 5 stars3 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
Condo 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

    $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