
House holiday rentals in Woodbury
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Top-rated house rentals in Woodbury
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1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!
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.

Fall Warwick Escape! Farms, Apple Pick, Ren Faire!
Fall is the BEST time to visit Warwick! You'll love this cozy & relaxing newly constructed home in the heart of Warwick's beautiful & historic Bellvale Hamlet. Enjoy the warm decor, great style, all new furniture, plenty of games & game table for pool or ping pong! Less than 10 minutes to Greenwood Lake, hiking, wineries, breweries, restaurants, Warwick Main Street, Bellvale Creamery & more! Nearby Pennings Orchard & Cidery, Legoland, Mountain Creek Resort & Spa. ~1 hr from NYC Permit # 33758

Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

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.

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.

Hillside Views in Hudson Valley
Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

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.

Cozy, Modern Retreat in the Woods of Cold Spring
Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

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.
Popular amenities for house rentals in Woodbury
House rentals with a pool

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

Charming cottage

Upstate Modern Scandinavian Barn in the Catskills

Simply Serene: Wild West City, 4 acres of privacy

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Modern House with Hot-Tub and Fireplace

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Weekly house rentals

The Best Lake House! *Ask About Boat Use Promo*

Perfect For Families and Large Groups

Modern creekside cabin in the Catskills

Eclectic one-bedroom house

Arkadia House Mid-century retreat with pool & view

Charming Cottage on 12 Secluded Acres + Hot Tub

Explore a Luxurious Lakefront with Private Beach

Crystal Cottage Retreat
Private house rentals

Nordic escape among tree tops

Sugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC

The Hudson Hideaway~Pool, Hot Tub, Sauna~1hr toNYC

Modern Usma Home, Walk to West Point. Hot Tub!

Elegant Hideaway: Cozy Cottage in Katonah, NY

Farmhouse w/ Sauna & Hot Tub near Storm King

Home in Cold Spring- Farm Stay!

Waterfront Lake House
Quick stats about house rentals in Woodbury

Total holiday rentals
Explore 20 holiday rentals in Woodbury

Nightly prices starting at
Woodbury holiday rentals start at $91 SGD per night before taxes and fees

Verified guest reviews
Over 240 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Woodbury holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Woodbury rentals

4.9 Average rating
Woodbury stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a washing machine and dryer Woodbury
- Rentals with pools Woodbury
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- Family-friendly rentals Woodbury
- Rentals with a firepit Woodbury
- Rentals with a patio Woodbury
- Rentals with a fireplace Woodbury
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Empire State Building
- Grand Central Terminal
- Bethel Woods Center for the Arts
- Statue of Liberty
- Rye Beach
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- The Metropolitan Museum of Art
- Astoria Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bronx Zoo




