Waterfront vacation rentals in Berkshire County

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Popular amenities for Berkshire County waterfront rentals

Waterfront apartment rentals

Superhost
A cozy living area is featured with a dark leather sofa and a light-colored armchair. A glass coffee table sits atop a patterned area rug. Wall sconces provide soft lighting, while a television and decorative fireplace are visible, enhancing the space's comfort.
Apartment in Pittsfield
5 out of 5 average rating, 4 reviews

Lavishly Appointed 2BR Apt. Home

RachelRating, 5 stars6 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!
A bright living area features a floral-patterned sofa and a wooden rocking chair. A wooden coffee table is placed in the center, adorned with brochures. Light enters through two windows, while a fire extinguisher is positioned near the door.
Apartment in Williamstown
4.83 out of 5 average rating, 215 reviews

Williamstown Apt. on Green River Walk to Williams!

CannieRating, 5 stars6 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!
Top guest favorite
A bright sunroom features large windows that allow natural light to illuminate the space. A gray and white patterned rug lies on the floor, complementing a cozy seating area with yellow cushions. A green dining table with chairs and potted plants add a touch of color.
Apartment in Great Barrington
4.89 out of 5 average rating, 27 reviews

Zen River Studio

EldadRating, 5 stars6 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.
Top guest favorite
Apartment in Lanesborough
5 out of 5 average rating, 41 reviews

Cozy Berkshire Waterfront Home

MarkRating, 5 stars2 months 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 !
A cozy living area features a light beige sectional sofa adorned with red and white striped cushions. A black coffee table sits at the center, complemented by wooden flooring. Artwork and decorative pieces are displayed on the walls, contributing to a warm atmosphere.
Apartment in Richmond
5 out of 5 average rating, 21 reviews

Private Main Floor of Cottage on Richmond Pond

AlanRating, 5 stars5 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 favorite
A modern bedroom features a plush King-sized bed with crisp white linens and decorative pillows. A door opens to an outdoor area, while a unique wall design adds architectural interest. A small console table with a coffee maker is positioned against the wall.
Apartment in Great Barrington
4.94 out of 5 average rating, 72 reviews

King Bed, Wi-Fi, 2m Ski Resort

MeghanRating, 5 stars2 weeks ago
Great find! My husband and I were visiting friends in GB and out dog sitting fell through, we searched around and found this great spot and were able to bring our furry friend with us. We are so glad we found this place! It was quiet and our anxious dog settled in so well - it felt like home to all of us.
Guest favorite
A wooden dock extends over a calm pond, framed by tall grasses on either side. The tranquil water reflects the surrounding trees, creating a serene natural setting, while distant cabins are visible along the shoreline.
Apartment in Otis
4.96 out of 5 average rating, 92 reviews

Enjoy every season the Berkshires have to offer.

AndreaRating, 5 stars2 months 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!
Guest favorite
A tranquil lakeside scene is depicted, showcasing a wooden dock reflecting in the calm water. Surrounding trees exhibit vibrant autumn colors, and a gazebo is situated on the shoreline, offering a serene retreat amidst nature.
Apartment in Hinsdale
4.8 out of 5 average rating, 5 reviews

Lakeside Getaway

AltonRating, 5 stars3 months ago
Very nice, clean space. Perfect for everything I needed for a long relaxing weekend!

Waterfront house rentals

Top guest favorite
A spacious living area features a wood-burning stove and large windows offering views of the waterfront. Natural light fills the space through skylights. Seating is provided by a sofa and two armchairs, while a dining area with red chairs can be seen in the background.
Home in Sandisfield
5 out of 5 average rating, 32 reviews

Waterfront oasis in heart of Berkshires

JoshuaRating, 5 stars4 months ago
Terrific experience. Would definitely stay again!!!
Guest favorite
Home in Becket
5 out of 5 average rating, 14 reviews

Private Lakehouse in the heart of the Berkshires

AaronRating, 5 stars6 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
An aerial view captures the tranquil setting of Lake Garfield, surrounded by colorful autumn foliage. The house is positioned near the water, showcasing nearby docks and residential properties. The landscape displays a serene and inviting atmosphere, with clear blue water reflecting the season's colors.
Home in Monterey
4.88 out of 5 average rating, 8 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars2 months 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 favorite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Family Fun at Hygge House on Richmond Pond

KatrinaRating, 5 stars6 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 favorite
A serene view of the house set among lush greenery, featuring a private sandy beach and dock extending into the lake. A canoe and kayak are visible on the shore, while the spacious yard offers a perfect spot for relaxation.
Home in Becket
4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

DaveRating, 5 stars5 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
A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars4 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 favorite
A serene view of a lakeside home is framed by lush greenery and large trees. The house features a white deck overlooking Pontoosuc Lake, with gentle waves reflecting the clear blue sky. The landscape reveals a spacious lawn leading towards the water.
Home in Pittsfield
4.96 out of 5 average rating, 54 reviews

Charming lake home with amazing sunset views

WilliamRating, 5 stars3 months 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
A spacious deck overlooks a tranquil lake, bordered by lush greenery and trees. Several white Adirondack chairs are positioned for relaxation, allowing guests to enjoy the serene water views. The deck's surface is wooden, providing a natural feel to the outdoor space.
Home in Becket
4.91 out of 5 average rating, 23 reviews

Lakefront Jewel By: Evergreen Home

JayRating, 5 stars1 week ago
We had an amazing stay! The house came with very detailed and easy-to-follow check-in instructions. The view was absolutely stunning, with the lake right in front of the property. We loved spending time kayaking and relaxing by the water. The place was clean, peaceful, and perfect for a getaway. Would highly recommend and would love to visit again!

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