Beachfront vacation rentals in Berkshire County

Find and book unique beachfront homes on Airbnb

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Popular amenities for Berkshire County beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
Home in Becket
4.96 out of 5 average rating, 70 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

JanieRating, 5 stars1 month ago
Private, secluded and cozy weekend away. The space was just as described and more private than expected. We loved waking up with the daylight and relaxing at night with the open sky and sauna sessions. Area recommendations were spot on and made the trip even more enjoyable. Hope to be able to get back during a different season to enjoy the area again!
Cabin in Plainfield
4.66 out of 5 average rating, 58 reviews

Camp on Windsor Pond- Berkshires

JoyceRating, 5 stars6 months ago
This is a great, no frills getaway. I don’t mean that in a bad way. It fit our needs perfectly. Plenty of room and comfortable. The view of the pond can’t be beat with the beach just steps from the front door. We saw two bald eagles our first morning there! Dani was a great host and always responsive.
Guest favorite
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!
Superhost
Home in Monterey
4.81 out of 5 average rating, 74 reviews

Rustic 3bd Lake Front Country Cottage

Kimberly JeanRating, 5 stars3 weeks ago
We enjoyed our 3 night stay. Jaryn was very responsive and his cabin is on a beautiful lake. The kitchen was well stocked with everything we needed. We enjoyed the downstairs entertainment/game room. Although the weather was cool we enjoyed spending time on the multi-level decks and docks. We would definitely go back.
Guest favorite
Home in Egremont
4.94 out of 5 average rating, 77 reviews

Modern and Stylish Country Lakeside Cottage

DylanRating, 5 stars2 months ago
fantastic and cozy, nice backyard, well equipped with amenities as well
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 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.

Private beachfront home rentals

Guest favorite
Home in Becket
4.94 out of 5 average rating, 147 reviews

Lake front retreat - Stylish Berkshire home

BetsyRating, 5 stars2 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!
Barn in Stockbridge
4.58 out of 5 average rating, 12 reviews

LAKE COTTAGE -In the Berkshire/ walk to Tanglewood

JaneRating, 5 stars34 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 favorite
Home in Egremont
4.94 out of 5 average rating, 77 reviews

Modern and Stylish Country Lakeside Cottage

DylanRating, 5 stars2 months ago
fantastic and cozy, nice backyard, well equipped with amenities as well
Top guest favorite
Cottage in Hinsdale
4.99 out of 5 average rating, 152 reviews

Cozy Cottage in the Berkshires

KateRating, 5 stars6 months ago
Staying at Sonya’s house was an amazing experience! The house is very clean, updated, quiet and had everything we needed! I highly recommend staying at the cottage on the lake. The porch was an extra spot that the sun shined all day! It truly was a beautiful weekend!
Guest favorite
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).
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 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 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.
Guest favorite
Home in Becket
4.96 out of 5 average rating, 70 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

JanieRating, 5 stars1 month ago
Private, secluded and cozy weekend away. The space was just as described and more private than expected. We loved waking up with the daylight and relaxing at night with the open sky and sauna sessions. Area recommendations were spot on and made the trip even more enjoyable. Hope to be able to get back during a different season to enjoy the area again!

Luxury beachfront home rentals

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

Lakefront home in the heart of the Berkshires

ChrisRating, 5 stars2 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 favorite
Home in Becket
4.94 out of 5 average rating, 147 reviews

Lake front retreat - Stylish Berkshire home

BetsyRating, 5 stars2 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
4.88 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.
Home in Otis
4.58 out of 5 average rating, 24 reviews

Lake house in the heart of the Berkshires

AmandaRating, 5 stars42 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