
Beachfront holiday rentals in Berkshire County
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Top-rated beachfront rentals in Berkshire County
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Popular amenities for beachfront rentals in Berkshire County
Pet-friendly beachfront home rentals

Camp on Windsor Pond- Berkshires
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 Was a chilly day, electric heater may be a bit outdated, but the space heater provided was perfect.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!

Enjoy every season the Berkshires have to offer.
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.

Rustic 3bd Lake Front Country Cottage
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.

Modern and Stylish Country Lakeside Cottage
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!

Berkshire Ski House on Lake Garfield W/HT By GB
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.

Campground Cottage near Tanglewood and Chatham
Private beachfront home rentals

Lake front retreat - Stylish Berkshire home
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!

Rustic 3bd Lake Front Country Cottage
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.

LAKE COTTAGE -In the Berkshire/ walk to Tanglewood
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.

Cozy Cottage on the Lake
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.

Modern and Stylish Country Lakeside Cottage
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!

Cozy Cottage in the Berkshires
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.

New Shaw Pond Skytop Retreat in the Berkshires
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).

Lakefront Cottage on Private Beach
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

Lakefront home in the heart of the Berkshires
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.

Lake front retreat - Stylish Berkshire home
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!

Lake house in the heart of the Berkshires
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.

Big Pond Hideaway
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! 🤗

Berkshire Ski House on Lake Garfield W/HT By GB
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.
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- Six Flags New England
- John Boyd Thacher State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Opus 40
- Naumkeag
- Brignole Vineyards
- Bull's Bridge Golf Club