Beachfront holiday rentals in Orange County

Lakefront Haven on Greenwood Lake

Escape to this peaceful lakefront retreat w/ stunning sunset views. 2BR/1BA+garage game room. Fish right off the new dock- there's plenty to catch! Enjoy two levels of outdoor decks with seating, grill, and fire pit for marshmallows under the stars. Dine al fresco just off the kitchen with stainless steel appliances. Close to boat accessible restaurants with live music. Inquire separately for boat rentals and deals with nearby marinas. Legoland, wineries, skiing/snowboarding, ziplining closeby!

The Mountaintop Lakehouse that Time Forgot.

Quiet Private lakehouse set down on 2 rare rock bluffs giving you a majestic water view just like it was in 1939. Extra Lg Great room w a huge fireplace. The great kitchen surrounds the chef. Big hot tub, Rowboat with canopy, 8 kayaks, Treehouse, Neverending Lakeside windows, docks, 1 hr from Manhattan w Eagles & vast wildlife like you were in the deep woods. Clean, unspoiled lake full of fish. Never had gas motors. A Mountaintop lake above the ski area. Stargazing! Perfect for get-togethers.

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

Greenwood Lake’s Iconic Lakefront “Icehouse”

Need a respite from the hustle and bustle of everyday life? This 4 Bedroom, 4 Bath home is located directly on the lake. Two floors of open living space with magnificent views of the lake and mountains. Families and couples can enjoy games indoors and out - with an expansive property and a chimenea fire pit and BBQ. A quick walk to Cove Castle Restaurant. 30 min drive to Legoland 20 min drive to wineries and breweries 15-20 min drive to NY Renaissance Faire PERMIT # 33387

Bungalow near West Point on Hudson River

Let your worries float away in the Hudson River as you relax at this Garrison vacation rental. This rare 3-bed, 2-bath gem is located over the railroad tracks with the river in your backyard. Boasting 2 floors of living space, a charming sunroom, beach and water access, a concrete pier, and view of Bear Mountain Bridge. You’ll also find historic sites, hiking trails, local shops, unique eateries, and charming towns like Cold Spring, Peekskill, & Beacon nearby!

Villa Adriana 4bdr 2 bath lake front dream home

Hello&welcome to Villa Adriana! Immersed amongst the trees and surrounding garden, perched on a slope overlooking Highland Lake, Villa Adriana is considered to have one of the best views of the entire lake. You can enjoy the spectacular view from the comfort of a cozy living room with large windows overlooking the lake, and from the adjacent roomy outdoor deck equipped with table, chairs, umbrella, and a BBQ grill for dining al fresco.

Stylish lake house, 3bd 2full bath, lake access

Get ready to experience the perfect lakeside getaway! This cozy, modern farmhouse has been fully renovated to offer the best of style and comfort. With 3BR's and 2 BA's, it’s the ideal spot for families or small groups looking to unwind. This home features a shared private beach just 50 yards from the lake—perfect for swimming, fishing, tubing or simply enjoying the view. We are 10 minutes from Mt.Peter & half hour from Vernon.

Lakefront Getaway 1 Hr from NYC

This spot is truly one of a kind. Enjoy stunning sunsets on the lake from the enclosed porch, just 10 feet from the lake. Small from the outside, spacious, new energy-efficient, warm and bright on the inside, with a "Cook's Kitchen". The natural beauty of the lake, the creek, the woods, with the cozy modern feel and amenities make this a perfect place to get away from it all, have a romantic weekend, or summer vacation.

Modern Lakefront | Dock • Hot Tub • Game Room

Modern lakefront home on the beautiful Greenwood Lake, NY! Enjoy boating, fishing, and water activities all summer long. In the fall and winter, enjoy nearby hiking & ski resorts! Home includes a private dock, gym, outdoor deck, grill, indoor fireplace, hot tub, and a basement game room. Four spacious bedrooms with a queen murphy bed in the loft. Rental Permit # 21-7783