Waterfront holiday rentals in Greenwood Lake

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Top-rated waterfront rentals in Greenwood Lake

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Guest favourite

Home in Woodstock

4.94 out of 5 average rating, 339 reviews

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.

Top guest favourite

Cabin in Margaretville

4.99 out of 5 average rating, 178 reviews

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

Top guest favourite

Home in Greenwood Lake

4.99 out of 5 average rating, 160 reviews

Lakefront Haven! Views, Beach, Firepit Free Kayaks

BOOKING FAST! Don't miss summer at the Lake! Escape to this beautiful 3BR home in Greenwood Lake! Experience the incredible lake views and our neighborhood beach to swim, launch kayaks, or fish, just steps away! You'll love the huge deck, cozy living area, firepit, ping-pong, free kayaks, paddleboard & well-equipped kitchen. Ideal for families or friends, this tranquil hideaway promises memories that will last a lifetime! Nearby wineries, breweries, restaurants, hiking, & more! 1 hour from NYC

Guest favourite

Cabin in Wurtsboro

4.97 out of 5 average rating, 336 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Top guest favourite

Home in Greenwood Lake

4.98 out of 5 average rating, 173 reviews

Coldwaters: hike, wineries, lake & mountain views!

Beautiful, comfortable home perched high on a hill across from Greenwood Lake, offering gorgeous views in a spacious, stylish setting, with lake & beach access. 5 minute drive to village restaurants & shops, and 15 to nearby Warwick and Tuxedo, this is the perfect setting for a relaxed & fun getaway no matter what your plans. You'll never want to leave, but you'll always remember you stayed! Book the guest house for an additional 2 bed, 1 bath apartment with kitchen! Permit #: 21-07657 A

Guest favourite

Cottage in Monroe

4.99 out of 5 average rating, 160 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Guest favourite

Home in Greenwood Lake

4.96 out of 5 average rating, 271 reviews

Stylish Lakeside Chalet with Hot Tub

Welcome to Greenwood Lakeside Chalet, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

Top guest favourite

Cottage in Weston

4.97 out of 5 average rating, 143 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Guest favourite

Cottage in Greenwood Lake

4.92 out of 5 average rating, 117 reviews

Oasis on the water 1 hour from NYC

We could all use a little therapy: LAKE THERAPY that is! There is nothing like water to heal what ails you. This entirely renovated cottage sits right on the water. Window views will have you believing you are living on a houseboat. Morning Coffee or evening cocktails on the deck are the perfect way to begin and end the day. The area is full of amazing things to do (guest book provided) Come for the weekend or stay the week. You will never want to leave!!

Top guest favourite

Cabin in Yulan

4.98 out of 5 average rating, 157 reviews

Waterfront Cozy A Frame - Enchanting River Cabin

Enchanting River is a magical 2BR 1Bath A-Frame home secluded on 4 acres of serine forest nestled beside beaver brook running right below the house. This magical get away is just 2 hours from NYC & 2.5 hours from Philly. Only 20 minutes to SKI BIG BEAR, a great snowboarding/ski mountain! As dawn turns to daybreak, there’s nothing more pleasant than being drawn from slumber by the sound of gushing water echoing through each surface of the property.

Guest favourite

Treehouse in Willow

4.96 out of 5 average rating, 797 reviews

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Guest favourite

Cabin in Livingston Manor

4.95 out of 5 average rating, 349 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek, gaze out XL windows, or cozy up by the fire—every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor—a quintessential Catskills town—and less than 2 hours from NYC.