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, 59 reviews

Camp on Windsor Pond- Berkshires

ArjunRating, 5 stars6 months ago
It was a wonderful experience staying in the middle of the nature. It was really peaceful and relaxing. Dani made it very easy and comfortable stay for us. We would definitely recommend the stay for a quick and peaceful gateway in nature.
Top guest favourite
Flat 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!
Superhost
Home in Monterey
4.81 out of 5 average rating, 75 reviews

Rustic 3bd Lake Front Country Cottage

ChristopherRating, 5 stars1 week ago
We thoroughly enjoyed our stay at this property—it was truly a delightful experience. The setting is serene, with beautiful views that made our time there feel peaceful and restorative. The house itself is exceptionally clean and full of character. We particularly appreciated the eclectic wall hangings throughout, which added a unique and personal touch to the space. The furniture was comfortable and evoked a charming 1970s vibe that we found both nostalgic and inviting. The kitchen is modern and well-equipped with everything one might need, making meal preparation easy and enjoyable. The beds and bedding were also very comfortable, ensuring a restful night's sleep. One of the true highlights was the abundance of outdoor space, which provided plenty of room to relax, gather, and take in the natural surroundings. All in all, this home was a real treat, and we’re grateful to have had the opportunity to stay here.
Guest favourite
Home in Egremont
4.94 out of 5 average rating, 78 reviews

Modern and Stylish Country Lakeside Cottage

SeanRating, 5 stars6 days ago
Hello - Great to be back in Maureen's home. Super excellent location 5mins or so to Great Barrington and close to everything the Berkshires has to offer. Home is really amazing for a romantic weekend away, my partner and I both loved everything about the home and the surrounding property. no notes.

Private beachfront home rentals

Guest favourite
Home in Becket
4.94 out of 5 average rating, 148 reviews

Lake front retreat - Stylish Berkshire home

BetsyRating, 5 stars3 weeks ago
We had a wonderful long weekend at Elle’s house. The bedrooms and living spaces were thoughtfully laid out and decorated beautifully. A short drive to lots of little cafés and hiking trails. We appreciated the quiet solitude of this little getaway in the Berkshires, and the ping pong table too. We didn’t get to use the lake (snow in April!) but hope to return to try again!
Superhost
Home in Monterey
4.81 out of 5 average rating, 75 reviews

Rustic 3bd Lake Front Country Cottage

ChristopherRating, 5 stars1 week ago
We thoroughly enjoyed our stay at this property—it was truly a delightful experience. The setting is serene, with beautiful views that made our time there feel peaceful and restorative. The house itself is exceptionally clean and full of character. We particularly appreciated the eclectic wall hangings throughout, which added a unique and personal touch to the space. The furniture was comfortable and evoked a charming 1970s vibe that we found both nostalgic and inviting. The kitchen is modern and well-equipped with everything one might need, making meal preparation easy and enjoyable. The beds and bedding were also very comfortable, ensuring a restful night's sleep. One of the true highlights was the abundance of outdoor space, which provided plenty of room to relax, gather, and take in the natural surroundings. All in all, this home was a real treat, and we’re grateful to have had the opportunity to stay here.
Barn in Stockbridge
4.58 out of 5 average rating, 12 reviews

LAKE COTTAGE -In the Berkshire/ walk to Tanglewood

JaneRating, 5 stars35 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
Home in Egremont
4.94 out of 5 average rating, 78 reviews

Modern and Stylish Country Lakeside Cottage

SeanRating, 5 stars6 days ago
Hello - Great to be back in Maureen's home. Super excellent location 5mins or so to Great Barrington and close to everything the Berkshires has to offer. Home is really amazing for a romantic weekend away, my partner and I both loved everything about the home and the surrounding property. no notes.
Top guest favourite
Cottage in Hinsdale
4.99 out of 5 average rating, 153 reviews

Cozy Cottage in the Berkshires

SteveRating, 5 stars7 months ago
Thanks for much for an amazing stay! Sonya took extra steps to ensure we enjoyed our time here. It was a cozy little cottage and the perfect little getaway. We will be back!
Guest favourite
Home in Becket
4.96 out of 5 average rating, 25 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars4 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, 31 reviews

Lakefront Retreat at Porcupine Place

LaurieRating, 5 stars1 month ago
Obsessed! if a house could be a soul mate I met mine! I don't say that lightly, I am everything real estate, holding, buying, selling, air bnbs, construction, sales and staging.......and this house could not have been any better. Cherishing the old, while putting new where needed. Let's you feel like you are at the lake without one thing on the to do list. Trees and water, seclusion without being alone. Everything in a logical, well thought out position. The experience from tennis to childlike wondering in the woods, with the most accommodating host that didn't overly reach out. I will be back for all of my peaceful getaways with my daughter. So very grateful for what this host offered us.
Guest favourite
Home in Becket
4.93 out of 5 average rating, 30 reviews

Lakefront Cottage on Private Beach

DaveRating, 5 stars6 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.

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