
Beachfront holiday rental in Berkshire County
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Top-rated beachfront accommodation in Berkshire County
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
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Popular amenities for Berkshire County beachfront rentals
Pet-friendly beachfront home rentals

Camp on Windsor Pond- Berkshires
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.

Enjoy every season the Berkshires have to offer.
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.

Rustic 3bd Lake Front Country Cottage
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.

The Cosmo Cottage
look forward to renting again 4 sure

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!
Private beachfront home rentals

Lake front retreat - Stylish Berkshire home
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!

Rustic 3bd Lake Front Country Cottage
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.

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 Retreat at Porcupine Place
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.

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

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! 🤗

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
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!

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