Beachfront holiday rentals in Berkshire County

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Berkshire County

Pet-friendly beachfront home rentals

Cabin in Plainfield
4.66 out of 5 average rating, 62 reviews

Camp on Windsor Pond- Berkshires

RhondaRating, 5 stars1 week ago
Nostalgic lake cabin with all the charm you would expect. Was a chilly day, electric heater may be a bit outdated, but the space heater provided was perfect. I would definitely visit again!
Top guest favourite
Flat in Otis
4.96 out of 5 average rating, 95 reviews

Enjoy every season the Berkshires have to offer.

MarieRating, 5 stars4 days ago
We had a lovely relaxing time. The place was in a quiet, beautiful spot. Denise’s instructions were helpful and she was very welcoming. The place was spotless and the bed was extremely comfortable. We’d happily stay there again.
Superhost
Home in Monterey
4.82 out of 5 average rating, 79 reviews

Rustic 3bd Lake Front Country Cottage

EdwardRating, 5 stars3 weeks ago
Peaceful, perfect getaway. Jaryn’s cabin on Lake Garfield was the ideal escape—cozy, quiet, and surrounded by nature. We loved the lake access, morning coffee on the porch, and how easy everything was.
Guest favourite
Home in Egremont
4.94 out of 5 average rating, 81 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars2 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Superhost
Home in Monterey
4.88 out of 5 average rating, 8 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars4 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.
Cabin in Austerlitz

Campground Cottage near Tanglewood and Chatham

Private beachfront home rentals

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 Monterey
4.82 out of 5 average rating, 79 reviews

Rustic 3bd Lake Front Country Cottage

EdwardRating, 5 stars3 weeks ago
Peaceful, perfect getaway. Jaryn’s cabin on Lake Garfield was the ideal escape—cozy, quiet, and surrounded by nature. We loved the lake access, morning coffee on the porch, and how easy everything was.
Barn in Stockbridge
4.58 out of 5 average rating, 12 reviews

LAKE COTTAGE -In the Berkshire/ walk to Tanglewood

JaneRating, 5 stars36 months ago
I had a wonderful stay at Ranne and Ray's amazing historic home. It is small and cozy, clean, well-supplied, and the hosts are gracious and generous in every way---right down to lending me a yoga mat! The location is ideal for everything one could want to do in the Berkshires.
Guest favourite
Cottage in Becket
4.81 out of 5 average rating, 53 reviews

Cozy Cottage on the Lake

PaigeRating, 5 stars5 months ago
The cottage was easy to check into, clean, and very cozy. It was decorated for the holidays which was perfect for our weekend. We enjoyed the fireplace and the games in the cabin as well! I would consider coming back in the summer to enjoy the outdoor area and lake. Ann-Marie and Carl provided really helpful instructions on how to get to the house.
Guest favourite
Home in Egremont
4.94 out of 5 average rating, 81 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars2 weeks ago
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!
Top guest favourite
Cottage in Hinsdale
4.99 out of 5 average rating, 154 reviews

Cozy Cottage in the Berkshires

MichaelRating, 5 stars1 month ago
Have stayed in Sonya’s cottage many times and each time is better than the last. Definitely the place I check for first when in the area.
Guest favourite
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
Guest favourite
Home in Becket
4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars2 weeks ago
Our family had an AMAZING stay in this cottage. It was clean and comfortable, and just what we were looking for. A quiet spot where we could enjoy fishing, kayaking, biking, etc with the comforts of home. Because of all the amenities offered, we didn’t have to pack too much which is always a bonus! We are already talking about our next visit 😊

Luxury beachfront home rentals

Home in Pittsfield
4.93 out of 5 average rating, 41 reviews

Lakefront home in the heart of the Berkshires

ChrisRating, 5 stars3 months ago
Great house and great location. We booked for a family ski vacation at Jiminy Peak. Convenient and easy trip over (less than 20 mins), and was lovely to come “home” to a spacious, well appointed house instead of the hotel room on-site. Siting on the lake looks ideal for other seasons as well. Highly recommend.
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!
Home in Otis
4.58 out of 5 average rating, 24 reviews

Lake house in the heart of the Berkshires

AmandaRating, 5 stars44 months ago
We loved our stay! The pictures were a great representation, but the view is even better in person. Lots of amenities, great location, clear instructions and communication.
Guest favourite
Home in Otis
4.97 out of 5 average rating, 32 reviews

Big Pond Hideaway

AnneRating, 5 stars3 weeks ago
A 5 star from wonderful bedding to the side tables to hold your coffee! Comfy chairs, throws for the chilly times and of course, the views and fire pit! Kitchen nicely appointed! Dave and Kathy, thank you for opening your home so graciously! We lacked for nothing! 🤗
Superhost
Home in Monterey
4.88 out of 5 average rating, 8 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars4 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.

Destinations to explore