Lake house vacation rentals in Berkshires

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Great Barrington, Cabin Sleeps 14, Walk To Town

You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Lovely Farm Cottage & Majestic Waterfall

The Sparrow House is a beautiful farmhouse with a private trail to a majestic 120' waterfall. With vintage wallpapers, eclectic antiques, a cozy fireplace, an outdoor cedar sauna, a large fenced in yard surrounded by honeysuckle vines and a spectacular mountain view, the house is a perfect getaway spot in unspoiled nature and still-wild forests of the Catskills. The waterfall is a truly magical place and considered a sacred site. The house is not appropriate for loud groups or parties. 🙏🦋🙌

HEAVEN ON EARTH - Hudson Riverfront Home

Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access year round. We provide kayaks & stand up paddle board. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Fish right off the lawn. Enjoy brunch, dinner or high tea in the Gazebo suspended over the Hudson with a private chef (inquire about availability). Explore Hudson, Saugerties, Woodstock....honestly, you'll not want to leave.

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Creekside Cottage

Set on the beautiful Esopus Creek, this lovely 2 BR, 2 bath home is perfect for a get-away w/family, friends or a romantic or creative retreat. It's just a 15-20 minute drive to the quaint Village of Saugerties, Kingston, Woodstock & Rhinebeck. Sit & watch the river run by on the screened porch or on the deck down by the river's edge, bbq (4 burner gas stove), play board games, take a kayak or swim in the river. Kitchen w/full amenities. Pets are not allowed unless pre-approved.

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.

Romantic getaway!3BDR/2BTH-HotTub/Sauna/Fireplace!

Welcome to The Camptons Cottage! Spending time at a stylish, fully renovated cottage can be a great way to have fun and create lasting memories. Enjoy the cozy atmosphere, explore the surroundings, and engage in activities that everyone will enjoy. Whether it’s soaking in the HotTub, enjoying backyard, playing games, having a barbecue, or simply relaxing together. This is pet friendly house (only one pet allowed per stay). Thank you!

Lakefront +pets +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.