Waterfront vacation rentals in Great Barrington

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Great Barrington 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 stars5 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!
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 stars5 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.
Guest favorite
A modern living area is furnished with a gray sectional sofa and an accent chair. A wooden coffee table sits between them on a light rug. Natural light filters through large windows, illuminating a mirror mounted on the wall. Decorative pillows add a pop of color.
Apartment in Valatie
4.95 out of 5 average rating, 189 reviews

Holland House: Modern Rustic Guest Apartment

JulieRating, 5 stars1 month ago
Seth is definitely a “super host”! Instructions were very detailed and perfect! The suggestions for restaurants and things to do was extensive. The location was perfect for our visit to Valatie. I have never been to an Airbnb that was this clean - impeccable! The small back porch with a view of the river was awesome! I will definitely book this Airbnb again!
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 !
Top guest favorite
A covered patio area is shown, featuring a wooden floor and two chairs next to a small table. The space is surrounded by screens, offering views of the grassy lawn and the Hudson River in the distance, with trees framing the scene.
Apartment in Coxsackie
5 out of 5 average rating, 111 reviews

Hudson River Beach House

BrandonRating, 5 stars6 days ago
This was the perfect spot and location for a getaway with my girlfriend. The unit is beautiful, clean and you can’t beat the view of the Hudson.
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 stars1 week 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!
Top guest favorite
Apartment in Pittsfield
4.96 out of 5 average rating, 78 reviews

The sweet place in the beautiful Berkshires!

CaitlinRating, 5 stars2 months ago
This was the second time we stayed at Theresa's place. Its a wonderful, clean apartment with all the amenities. More importantly Theresa and her partner are amazing hosts. For example, there were back to back snowstorms when we were there and they were wonderful about making sure the area was safe and we could get out! We look forward to our next visit.

Waterfront house rentals

Guest favorite
A dining area features a wooden table surrounded by six chairs, with two additional seats visible. Large glass doors provide a view of Glass Lake, while warm wood paneling and beams create an inviting atmosphere. Natural light floods the space, enhancing its connection to the outdoors.
Home in Averill Park
4.98 out of 5 average rating, 174 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

KathleenRating, 5 stars3 weeks ago
First of all, a 1 o’clock check in started us off on a very happy note. Then, having room for each female to have her own bed made a for peaceful stay. The biggest thing was how much the space was warm, comforting, and full of character. The sliders provided a broad view of the lake. The kitchen with the open area to dining and front area provided an open concept feel to an older home while maintaining its true character. The tall cabinets contained every utensil/small appliance that we needed and more. We brought a bag of board games as we know what we like, but there was a great variety already there. While there was plenty of room, we felt “together” in that space. We can only imagine the beauty that arrives later in spring. Thank you for having us!
Guest favorite
An open-plan living and dining area features large windows providing ample natural light. A dining table with floral-patterned chairs sits next to a cozy seating arrangement, which includes a light-colored sofa and a stylish armchair. A wooden mirror and decorative accents enhance the modern design.
Home in Becket
4.94 out of 5 average rating, 146 reviews

Lake front retreat - Stylish Berkshire home

CynthiaRating, 5 stars2 months ago
We loved our stay at this lakeside cottage! Quick 12 minute drive to Otis Ridge for skiing. Elle was super responsive. The house fit all our needs for two families with young kids - great space for hanging out, lots of perks for the kids, the ping pong table was a hit. We’d love to stay here again in warmer weather.
Guest favorite
A covered porch features comfortable seating arrangements with wicker sofas and a coffee table. The view overlooks a serene lake, framed by trees and a cloudy sky. The patio area offers potential for relaxation, with easy access to lovely outdoor scenery.
Home in Craryville
4.91 out of 5 average rating, 46 reviews

Cozy Lakefront House close to Ski Mountains

SamanthaRating, 5 stars6 months ago
Wonderful, attentive, and responsive hosts! Their home is in a beautiful location, with views of/ access to the lake. We would love to come back.
Guest favorite
Home in Athens
5 out of 5 average rating, 20 reviews

Modern 4 season lakefront rental

KatieRating, 5 stars6 months ago
An amazing house for a family stay in the Catskills area. Antonia has designed a beautiful home, with so many unique retro nods and details. The basement is an awesome additional space for everyone to hang out in. The backyard set up is also great- with easy access to the hot tub and a few steps to the lake. 15 min drive to great restaurants and things to do-Loved our stay here!
Guest favorite
A bright living space features large floor-to-ceiling windows that allow natural light to fill the room. A cozy seating arrangement includes modern chairs and a round coffee table on a patterned rug, with a view of the trees and lake visible through the glass.
Home in Valatie
4.97 out of 5 average rating, 30 reviews

Majestic lake front house

MagdalenaRating, 5 stars2 months ago
This really was a perfect stay with an incredible view! We had an amazing stay at this Airbnb! The view was absolutely breathtaking, just as shown in the pictures. The bed was incredibly comfortable, and we felt right at home from the moment we arrived. The kitchen was spacious and well-equipped, making it easy to prepare meals. Everything was exactly as described, and we couldn’t have asked for a better experience. Highly recommend!
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.
Top guest favorite
A combined living and reading area features wooden beams above and a plush armchair. A decorative arrangement of branches is placed on a side table, accompanied by a cozy throw on the chair. Built-in shelving displays books and decor, with natural light illuminated through the nearby window.
Home in Hudson
4.95 out of 5 average rating, 372 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

KelleyRating, 5 stars1 week ago
We loved staying at Jeffrey and Juan’s quiet home on the rushing Chittenden Creek! Jeff is a communicative, friendly, and accommodating host and would absolutely recommend his place to others. I surprised myself at how much I loved the bird watching (don’t worry, Jeff has binoculars and a book to guide you!). Don’t miss out on the Empire trail for early evening walks! My husband and I stayed at their home for two weeks as we both work remotely and there was plenty of space to spread out and take calls. The plant room in their home is so beautiful that people complimented my ‘digital’ background on zoom! Would absolutely stay again.
Guest favorite
A spacious dining area is highlighted by a large black table that seats eight, surrounded by wooden chairs with woven seats. A warm brick wall features decorative accents, while a bookshelf holds various books. Natural light enters through nearby windows, illuminating the wooden floor.
Home in Staatsburg
4.96 out of 5 average rating, 118 reviews

Light and Spacious Designer Retreat near Rhinebeck

JaniceRating, 5 stars3 months ago
Great spot for our family weekend! Plenty of room, large well supplied kitchen easy “check in” and great communication with host!

Quick stats about waterfront rentals in Great Barrington

  • Total rentals

    20 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    880 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore