Waterfront holiday rentals in Berkshire County

Find and book unique waterfront accommodation on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Berkshire County waterfront rentals

Waterfront apartment accommodation

Apartment in Pittsfield
5 out of 5 average rating, 4 reviews

Lavishly Appointed 2BR Apt. Home

RachelRating, 5 stars4 months ago
A charming place and cozy stay! Robert was responsive and friendly. Also, I highly recommend the shrimp and cheddar grits at District Bar & Kitchen which is only a few minutes away. So good!
Apartment in Williamstown
4.83 out of 5 average rating, 214 reviews

Williamstown Apt. on Green River Walk to Williams!

CannieRating, 5 stars4 months ago
Very convenient to the college and Spring St shops and restaurants; very walkable. Plenty of room for 5 people and found the washer/dryer very useful. Added bonus were the fall colors and the sound of water from the creek. Molly very responsive to questions and timely. Very clean. Thanks!
Guest favourite
Apartment in Great Barrington
4.89 out of 5 average rating, 27 reviews

Zen River Studio

EldadRating, 5 stars4 months ago
we enjoyed our stay at this beautiful inviting cozy place. On top of the having most any amenities one can think of, the place is situated at a great place to explore Western Massachusetts from. we got all the help we needed to get around during our stay, places to visit, the better places to eat etc. I will definitely recommend my friend to stay there. thank you much Jill and Steve for creating this place.
Apartment in Williamstown
4.67 out of 5 average rating, 24 reviews

Lovely two bedroom river-view rental unit

ClaireRating, 5 stars4 months ago
Overall, we had a good stay here. There was some noise from the street, but it was not an issue for me. If you are a very light sleeper, this might be something to consider. The queen bed was very soft/squishy, which again I like, but if you prefer a firmer mattress, keep that in mind. The place was extremely clean and easy to access for check-in.
Guest favourite
Apartment in Lanesborough
5 out of 5 average rating, 41 reviews

Cozy Berkshire Waterfront Home

MarkRating, 5 stars2 weeks ago
Can’t say enough good things about this find near Jiminy Peak in the Berkshires! Stayed for three nights while skiing two days over presidents weekend. Hosts were very thoughtful and flexible. Left cookies and s’mores kit which were a nice touch. During snowstorm steps to the unit and walking areas were kept shoveled and salted. For us and our two teenagers this offered the perfect alternative to pricey on mountain lodging and was only about a 13 minute drive. There was even a bonus game room which could probably serve as a small additional bedroom if someone had the need, it certainly has room for a twin air mattress. Our two kids shared the queen bed with minimal fighting, but that would’ve been our back up plan😂. Anyway, they were super responsive, check in and check out was easy and will certainly look to stay again if we get up there to ski again this year !
Apartment in Richmond
5 out of 5 average rating, 21 reviews

Private Main Floor of Cottage on Richmond Pond

AlanRating, 5 stars3 months ago
Beautiful location overlooking the pond, conveniently located to towns and attractions, and private. Cozy, well stocked kitchen/cooking gear, everything you need as a contained retreat or a home base while exploring the Berkshires.
Guest favourite
Apartment in Great Barrington
4.94 out of 5 average rating, 66 reviews

King Bed, Wi-Fi, 2m Ski Resort

StephanieRating, 5 stars1 week ago
Nice spot! Design was really nice. Bed was so comfortable. Perfect place for a couple nights. Walkable to restaurants or close car rides to lots of places and ski mountains. Would stay again for sure!
Guest favourite
Apartment in Otis
4.96 out of 5 average rating, 92 reviews

Enjoy every season the Berkshires have to offer.

AndreaRating, 5 stars2 weeks ago
Extremely clean and peaceful place. Very cute and cozy set up as well! Denise and John are excellent hosts. Upon leaving, our car unfortunately got stuck a mile out from the house in some deep snow. John saved the day and immediately came to the rescue to tow us out. His kindness and quick response saved me a lot of stress. Highly recommend John and Denise for their exceptional hospitality and willingness to go the extra mile!

Waterfront house rentals

Guest favourite
Home in Sandisfield
5 out of 5 average rating, 32 reviews

Waterfront oasis in heart of Berkshires

JoshuaRating, 5 stars2 months ago
Terrific experience. Would definitely stay again!!!
Guest favourite
Home in Becket
5 out of 5 average rating, 14 reviews

Private Lakehouse in the heart of the Berkshires

AaronRating, 5 stars4 months ago
I want to say thank you to Christopher and his family for allowing my friends and me to stay in their home. it was clean, beautiful, serene and exactly what it was described to be. Christopher, your suggestions on golf courses for my friends and me were exceptional. I hope we were as good of guests as you were hosts!
Superhost
Home in Monterey
4.86 out of 5 average rating, 7 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars3 weeks ago
This house was great for a winter weekend getaway! Great Barrington, Lenox, and Stockbridge are all adorable towns to visit and are a 15 - 30m drive away. The house itself was cozy and had all the amenities we needed. Shay was very responsive. Something to know about the area is that ride shares and cabs are hard to come by, so having a car that fit everyone we were traveling with was crucial for our group to get around town.
Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Family Fun at Hygge House on Richmond Pond

KatrinaRating, 5 stars4 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.
Guest favourite
Home in Becket
4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

DaveRating, 5 stars3 months ago
Daphne is a thoughtful and wonderful host. The property was clean, comfortable and very well appointed with everything I would need, especially in the kitchen. I highly recommend this 5-star property. It is quiet, peaceful and full of nature everywhere the eye can see.
Superhost
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

Ski at The 19th c. Barn in The Berkshires

JohnRating, 5 stars2 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Guest favourite
Home in Pittsfield
4.96 out of 5 average rating, 54 reviews

Cozy winter getaway close to skiing & ice fishing

WilliamRating, 5 stars1 month ago
My girlfriend and I spent four nights days at Joe and Jess’s beautiful home for a much needed vacation after the holidays. We spent most of our days/nights in the sunroom playing board games and watching movies with the beautiful view of the lake. It snowed halfway through our stay and the snow on the lake made it truly feel like we were in a winter wonderland. The house was very clean and we had everything we needed to cook our meals. We would love to come back during the warmer months and explore the lake as well as some of the hiking trails nearby.
Superhost
Home in Becket
4.9 out of 5 average rating, 20 reviews

Lakefront Jewel By: Evergreen Home

AldiasRating, 5 stars2 months ago
great place to spend your time with family. they provide many things which is awesome. we definitely like to go back. Great cabin. we love it and enjoyed it.

Destinations to explore