Holiday rentals with lake access in Lenox

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Magical Private Island Retreat in Pine Plains

Enjoy the serenity of Twin Island Lake, surrounded by tranquil water, lush mountains and nature. this incredible private island retreat is only 2 hours from NYC. Take a canoe across a lily pad dotted lake to your own private island paradise. You will never find a magical space like this so close! The entire island is yours to enjoy and has plenty of outdoor spaces including a propane grill, hammocks and plenty of seating areas. The inside a humble aesthetic with wood paneling and charm.

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish glamping cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood & fantastic interior design. Unwind in the reading nook, master bedroom with skylights, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9-minute walk or 2-minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood is just minutes away.

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

The House of Pi

Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!