
Beach house holiday rentals in Tanglewood
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Top-rated beach house rentals in Tanglewood
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5 BR Lakefront House w/ Hot Tub - Catskills
Please enjoy the tranquility and relaxation that lake-life has to offer at our lakeside property on Sleepy Hollow Lake. Our hilltop house, nestled in the trees, alongside a quiet cove, allows for one of the more private areas on the lake. Enjoy a retreat at the lake or explore all that the area has to offer. We are located 2 hours north of New York City and about 20-40 minutes from Catskill, Hudson, Saugerties, Woodstock, and Albany, and Hunter and Windham Mountains. The main floor has an open plan convenient for family style entertaining and cooking. There is a full kitchen, a good-sized kitchen island with seating, a dining table that seats 8 people, and a living room for gathering. Bring the meal outside with our dining and barbecue set on the deck while enjoying the lake-side views. This main floor has the master suite with a king bed and a jack-and-jill bathroom, a bedroom with a queen-sized bed, and a room with two twin beds. The bottom floor has the TV and game lounge with two bedrooms; one queen-sized bed and one full bed. There is also a laundry space on this floor and a bathroom. Right outside, we have a 6 persons hot tube. From this floor you can walk out and descend to our private lake dock for kayaking and canoeing. You may also enjoy fishing or just sunbathing on the dock with a glass of wine. The house is located on a quiet cove with a dock and a broad private lake front, from which we cannot hear motor boats. We have 5 kayaks, a 3-person canoe, paddles and lifejackets that guests can use after reading lake navigation rules available in the house; Guests use the kayaks, the canoe, the life jackets, and paddles at their own risk, and agree to taking full responsibility for using the kayaks and canoe, at their own risk. Guests need to bring life jackets that fit their children to use the kayaks and canoe. Fishing is allowed on the lake. Guests also have access to the lake community shared amenities, including swimming pools (~mid-May to ~mid-September), a marina, a sand beach, tennis courts, bocce ball courts, basketball courts, volleyball courts, a baseball/softball field, a golf driving range, playgrounds, a dog park, and a doggy beach. The house has multiple desks to work comfortably, and the highest speed internet available.
5.0 out of 5 average rating, 67 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!
4.92 out of 5 average rating, 180 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.
4.95 out of 5 average rating, 192 reviews
Up to 10 ppl w/ central air, parking, pond &kayaks
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.
4.74 out of 5 average rating, 172 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.
4.95 out of 5 average rating, 56 reviews
Artsy lake house on an island
This brand new impeccably renovated Hudson Valley 3-bed offers everything for an amazing lake 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
4.94 out of 5 average rating, 48 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.
4.95 out of 5 average rating, 94 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!
4.95 out of 5 average rating, 256 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.
4.87 out of 5 average rating, 169 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.
4.94 out of 5 average rating, 47 reviews
Twin Island Lake House • Hot Tub
Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great area for hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.
4.97 out of 5 average rating, 141 reviews
Lakefront Retreat w/ Dock, Sunset Views + Beach
Welcome to our lakefront cottage on Burden Lake—your perfect spring and summer escape. Wake up to coffee on the private deck, spend your days swimming, kayaking, or relaxing on the seasonal dock, and wind down with sunset views by the fire pit. Bright, comfortable spaces with two decks, outdoor shower, and a small beach perfect for kids. Sleeps 5 (queen, twin bunks, twin). Just 20 min to Albany, 25 to Jiminy Peak, 40 to Saratoga. Easy, breezy lake days await.
5.0 out of 5 average rating, 8 reviewsPopular amenities for Tanglewood beach house rentals
Beach house rentals with a pool

Waterfalls and Trails at 'The Mills At Green Hole'
5.0 out of 5 average rating, 54 reviews
Lake House close to Skiing & Indoor Hot Tub
4.96 out of 5 average rating, 112 reviews
Private lakefront home, hot tub & resort amenities
4.95 out of 5 average rating, 192 reviews
Modern-Chic Athens Home - Fish, Ski & Swim!
4.95 out of 5 average rating, 94 reviews
5 BR Lakefront House w/ Hot Tub - Catskills
5.0 out of 5 average rating, 67 reviewsPrivate beach house rentals

Hudson River 1830s cottage w/ private beach!
4.71 out of 5 average rating, 102 reviews
Designer Lakefront house, a hiking-ski retreat.
4.74 out of 5 average rating, 121 reviews
Lake House close to Skiing & Indoor Hot Tub
4.96 out of 5 average rating, 112 reviews
Lake front retreat - Stylish Berkshire home
4.92 out of 5 average rating, 180 reviews
HEAVEN ON EARTH - Hudson Riverfront Home
4.95 out of 5 average rating, 256 reviews
Dreamy Hudson Valley Lakehouse with Hot Tub
4.87 out of 5 average rating, 169 reviews
Private lakefront home, hot tub & resort amenities
4.95 out of 5 average rating, 192 reviews
Linny's | Private Dock | Lake Access | Firepit
4.97 out of 5 average rating, 140 reviewsPet-friendly beach house rentals

Hudson Riverfront home w/ private beach
4.98 out of 5 average rating, 62 reviews
HEAVEN ON EARTH - Hudson Riverfront Home
4.95 out of 5 average rating, 256 reviews
Dreamy Hudson Valley Lakehouse with Hot Tub
4.87 out of 5 average rating, 169 reviews
Private lakefront home, hot tub & resort amenities
4.95 out of 5 average rating, 192 reviews
Majestic lake front house
4.95 out of 5 average rating, 56 reviews
Forest Hollow | Waterfront • Kayaks • Wood Stove
4.85 out of 5 average rating, 99 reviews
Artsy lake house on an island
4.94 out of 5 average rating, 48 reviews
Modern-Chic Athens Home - Fish, Ski & Swim!
4.95 out of 5 average rating, 94 reviewsDestinations to explore
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- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- June Farms
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Kent Falls State Park
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Ski Sundown
- Rensselaer Polytechnic Institute
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- Poets' Walk Park
- New York State Museum





