Beach house holiday rentals in Tanglewood

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Top-rated beach house rentals in Tanglewood

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Top guest favourite

Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.

Home in Athens

4.94 out of 5 average rating, 176 reviews

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, kayaks, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, or work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking, art galleries, antique shops, and cultural centers.

Superhost

A bright living area features a cozy sofa with a soft throw, complemented by an orange accent chair. A coffee table displays a potted plant and books. Large windows allow natural light to illuminate the space, with a modern kitchen visible in the background.

Home in Becket

4.91 out of 5 average rating, 169 reviews

Lake front retreat - Stylish Berkshire home

Experience total privacy at this beautiful mid-century home with 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly getaway offers exclusive lake frontage, complete with a dock & 4 kayaks for endless adventures! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Just 15 minutes from Downtown Lee, close to outlets, hiking trails, and Otis Ridge skiing!

A charming house is surrounded by lush greenery and colorful flowerbeds. A gravel driveway leads up to the home, with a gazebo visible in the background. Comfortable seating areas on the porch invite relaxation amidst the tranquil landscape.

Home in Plainfield

4.74 out of 5 average rating, 169 reviews

Winter luxury w/ a fireplace, indoor parking, pond

Secluded Berkshire house surrounded by 10,000 acres forest is with marked trails & pond that sleeps up to 10 people comfortably. Central air & heat, fireplace, propane BBQ & charcoal BBQ & smoker BBQ, Fibre high-speed WiFi gigabit internet (new in January 2020), Roku streaming device with Netflix & Amazon Prime & hundreds more channels, gazebo, private pond, comfy mattresses/beds, 2 bathrooms, new laundry dryer, 16 foot C shaped couches, indoor garage parking, vegetable gardens, kayaks & more.

Guest favourite

A modern living space is featured with large windows allowing natural light to fill the room. Comfortable seating, including a plush sofa and stylish chairs, surrounds a wooden coffee table. A patterned area rug adds warmth to the sleek, tiled floor.

Home in Valatie

4.96 out of 5 average rating, 50 reviews

Majestic lake front house

Experience the ultimate retreat at our 2,100 sq ft 2 bedroom, 2.5 bathroom, modern lake front property. Enjoy swimming, fishing, free kayaking and paddle boarding on our Private Lake. Relax and unwind at our Outdoor Fire Pit or simply enjoy the picturesque view out of our floor to ceiling picture windows. Your Dream Family Reunion at our Secluded 26-acre Property awaits. We are also open to host a small, QUIET Wedding or similar event. There is no review yet, it is newly up for str.

Guest favourite

Home in Copake

4.94 out of 5 average rating, 36 reviews

Modern ski house close to Catamount Mountain

This brand new impeccably renovated Hudson Valley 3-bed offers everything for an amazing winter getaway Outdoors: Deck+grill, adirondack chairs + view of lake + winter wonderland; kayaks, stand-up paddle boards + tubes Indoors: Fireplace; 3 bedrooms with queen-sized beds; pull-out couch in second living room; kids room 10 minutes to Catamount; 15 to Millerton + Hillsdale; 25 to Hudson + Great Barrington; 40 minutes to Tanglewood + Lenox; 45 to Rhinebeck Ski, hike, restaurants, golf, lake

Superhost

Home in Rhinebeck

4.83 out of 5 average rating, 291 reviews

Private Lakefront Bungalow

Outside Rhinebeck, renovated sunny 2 bedroom bungalow on Silver Lake. Private lakefront sandy beach, dock, canoe, kayak, paddle board + outdoor fire pit. Great fishing + swimming. Smart TV, projector w apple tv with woodstove. Newly remodeled eatin kitchen. The house includes to private 2 queen bedrooms and additional sleeping loft with a full bed. Large master bedroom with vaulted ceilings, private bath, and french doors leading out to deck with lake view. Additional outhouse workspace.

Guest favourite

A spacious living area features a comfortable sofa and two armchairs arranged around a central coffee table. Natural light floods in from a nearby window, illuminating a textured area rug. A decorative plant adds a touch of greenery, creating an inviting atmosphere.

Home in Athens

4.94 out of 5 average rating, 85 reviews

Modern-Chic Athens Home - Fish, Ski & Swim!

Feel as if you've stepped into a home magazine when you arrive at this roomy 5-bedroom, 2.5-bathroom house! You'll adore the vacation rental's stylish decor, high-end amenities, and the variety of sleeping arrangements to ensure everyone in your party is satisfied. Plus, the abode is nestled in the perfect spot to access endless opportunities for fun including Sleepy Hollow Lake, downtown Athens, various Hudson River preserves, and more. Come weary, leave rejuvenated at this welcoming home.

Top guest favourite

A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.

Home in Catskill

4.95 out of 5 average rating, 233 reviews

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!

Guest favourite

The exterior of the home is illuminated at dusk, showcasing a multi-level structure with numerous large windows. The well-maintained lawn features stone pathways, and outdoor seating areas are visible. Surrounding trees offer a natural backdrop, enhancing the tranquil setting.

Home in Pittsfield

4.93 out of 5 average rating, 43 reviews

Lakefront home in the heart of the Berkshires

Lakefront, close to skiing, hiking, restaurants, Tanglewood and everything the Berkshire county has to offer. 4 bed/4 bath and additional sleeping area in lower level. Large open layout with two living areas overlooking the lake. Master bedroom with a wall of windows and amazing views, balcony. Three decks to enjoy the views and a patio with built in firepit for colder nights. Jiminy peak skiing 20 min, Tanglewood 20 min, Berkshire Museum 10 min, and lake, dock, and kayaks right outside.

Guest favourite

Sunlight glimmers on the calm water surface at sunset, framed by tall trees. A hammock is visible on the ground, while a private dock with two Adirondack chairs provides a serene spot to relax. Colors of autumn foliage add warmth to the scene.

Home in Copake

4.87 out of 5 average rating, 158 reviews

Dreamy Hudson Valley Lakehouse with Hot Tub

Hello, hygge! Our renovated lakehouse on idyllic 100-acre non-motorboat Robinson Pond was designed as our dream getaway. Soak in the water views from every room, walk onto the deck or patio (and hot tub!) from sliding doors that let the outside in, kayak or paddle board from our private dock, project movies on the big screen, make pizzas in the outdoor oven, play foosball or air hockey, sit around the wood burning stoves or fire pits, walk to sandy beaches and marvel at all the wildlife.

Guest favourite

Home in Palenville

4.98 out of 5 average rating, 43 reviews

Giant Serene Private Luxury Creekside Home

Sprawling Private 2 Bedroom and more nestled in the Catskills magical Kaaterskill Clove. As you walk through the front doors relaxation washes over you. Dine at the farmhouse table with the mountain and garden view. Stargaze on the patio, and cuddle up on the oversized couches. Luxury 1st floor and more of a 1892 home. Very private, beautiful 2-family home on Kaaterskill Creek. Private quiet office space with blazing fast WiFi Ideal for families, friends, 2 couples on vacation.

A spacious wooden deck is surrounded by trees and overlooks the lake. Soft lighting from string lights creates a warm ambiance. A round dining table with several chairs is placed in the center, offering a comfortable space for outdoor meals.

Home in Pine Plains

4.77 out of 5 average rating, 112 reviews

Designer Lakefront house, a hiking-ski retreat.

Lakefront property at its finest, recently renovated designer house. Beautiful Twin Island Lake. The peace and tranquillity of a non-motorboat lake is something to truly love & enjoy. Enjoy kayaking or just resting on the large deck that overlooks the beautiful Lake; our family summer home and we put much care into ints maintenance; You will find everything in the house of high quality. A remote sanctuary minutes from the town, this home delivers the much-needed 'Good Life'.