House holiday rentals in Monroe

Cozy up on the lake! Hot tub/Firepit open all year

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Aster Place

A beautiful and cozy home nestled in the Forest Hills section of Greenwood Lake, just over an hour outside of New York City. Boasting nearby activities in each season, including wineries, skiing and lake activities, this is a perfect year-round retreat. located 1/2 mile from our quiet community beach allows for a serene daily chill by the water. Town center is a short drive away, or 15 minutes from all that Warwick has to offer, you will enjoy this perfect setting for your lakeside getaway!

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

The Wine & Wilderness Hideaway [Cal King •1hr NYC]

*COZY UP IN OUR FALL OASIS NOW! Nature’s haven, indulge in seamless spacious single-level living! Minutes away from Mountain Creek Spa & Water park, Warwick wineries, breweries, creameries & apple picking, scenic hiking trails, serene lakes, enchanting parks, & indulgent restaurants. Open concept, Chef's kitchen, Dishwasher, Washer & Dryer, 2 BR, 2 Bath, Cal King bed w primary BR attached to private Bath w soaking tub a retreat to relaxation. Huge patio & fireplace create everlasting memories

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

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

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).

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.

Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

Modern Woodland Retreat, Hudson Valley & Catskills

A dreamy forest retreat wrapped in trees and good light—perfect for couples or families. Lounge on the deck, sip wine by the fire pit, or sleep in under plush bedding. Inside, you’ll find a fully stocked kitchen, organic toiletries, toys, books, and baby gear—all thoughtfully chosen for comfort and ease. Minutes from Beacon, New Paltz, and Harriman State Park for hikes, river towns, swimming holes, farmers markets, and slow mornings that stretch into golden afternoons.

Millionaire Mansion Countryside Stay w/ Lrg Hottub

You'll be staying in a millionare mansion in the town where cream cheese was invented. Immerse in the fresh upstate NY nature nearby farms! Sugarloaf antique village, famous vineyards, luxury shopping, amusement parks, hiking, swimming, and restaurants. Surround yourself with mountain views through floor-to-ceiling windows spilling shimmering light into spacious rooms. Every room flows effortlessly into the next, naturally creating the space for deep connections.