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
4.67 out of 5 average rating, 64 reviews

Camp on Windsor Pond- Berkshires

JenniferRating, 5 stars1 week ago
The cabin is in a beautiful location with the pond right across the street. It’s not a luxury stay but if you are just looking for a scenic location near the berkshires it is great.
Top guest favourite
Flat in Otis
4.96 out of 5 average rating, 97 reviews

Enjoy every season the Berkshires have to offer.

MicheleRating, 5 stars6 days ago
The space is very clean. I stayed 2 nights and brought my dog with me. The only thing that I was surprised about was that there wasn't a door to the bedroom area. I had looked at the pictures and assumed the door I saw was to the bedroom but it was a closet. The bed area is separated by a partial wall but not an actual door. Something to keep in mind if you have additional people sleeping on the pull out couch.
Superhost
Home in Monterey
4.83 out of 5 average rating, 80 reviews

Rustic 3bd Lake Front Country Cottage

SarahRating, 5 stars1 week ago
Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.
Cabin in Austerlitz

The Cosmo Cottage

BrianRating, 5 stars1 week ago
look forward to renting again 4 sure
Guest favourite
Home in Egremont
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 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!

Private beachfront home rentals

Guest favourite
Home in Becket
4.94 out of 5 average rating, 150 reviews

Lake front retreat - Stylish Berkshire home

ShaiRating, 5 stars2 weeks ago
We had a wonderful time at this beautiful lake house! The home itself is lovely—spacious, comfortable, and perfect for a family getaway. The lake and boats were a big highlight for us, offering plenty of fun and relaxation. Our host was incredibly responsive and helpful throughout our stay. While there were a few small things that needed fixing, she addressed them right away and was very communicative, which we really appreciated. Overall, it was a great experience and a memorable holiday for our family. We’d definitely love to come back!
Superhost
Home in Monterey
4.83 out of 5 average rating, 80 reviews

Rustic 3bd Lake Front Country Cottage

SarahRating, 5 stars1 week ago
Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.
Guest favourite
Cottage in Becket
4.81 out of 5 average rating, 54 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
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 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).
Top guest favourite
Home in Tolland
5 out of 5 average rating, 33 reviews

Lakefront Retreat at Porcupine Place

BrianaRating, 5 stars1 week ago
This place was beautiful and very peaceful. The neighborhood is super quiet. It was a great place to stay and wake up in the morning and drink my morning coffee while listening to nature and look out at cranberry pond. Unfortunately it was a very busy weekend due to staying here for a wedding so I did not get to fully enjoy this cute place that included a paddle boat, fire pit and kayaks. I would definitely recommend this quiet get away to anyone looking for a peaceful vacation or an outdoor vacation with the kids at the lake. The host was also super responsive and helpful during my stay. Only challenging thing that happened which might not happen for everyone is the address had me a couple campsites before the actual location (got to love technology and GPS right). We were able to find it once we drove a little bit farther. However this could have just been my GPS but wanted to give people the heads up if they are also in my position and coming during the nighttime.
Guest favourite
Home in Becket
4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars3 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

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

Big Pond Hideaway

AnneRating, 5 stars1 month 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! 🤗
Home in Pittsfield
4.93 out of 5 average rating, 41 reviews

Lakefront home in the heart of the Berkshires

ChrisRating, 5 stars4 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, 150 reviews

Lake front retreat - Stylish Berkshire home

ShaiRating, 5 stars2 weeks ago
We had a wonderful time at this beautiful lake house! The home itself is lovely—spacious, comfortable, and perfect for a family getaway. The lake and boats were a big highlight for us, offering plenty of fun and relaxation. Our host was incredibly responsive and helpful throughout our stay. While there were a few small things that needed fixing, she addressed them right away and was very communicative, which we really appreciated. Overall, it was a great experience and a memorable holiday for our family. We’d definitely love to come back!
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.

Destinations to explore