
House vacation rentals in Woodbury
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Top-rated house rentals in Woodbury
Guests agree: these houses are highly rated for location, cleanliness, and more.

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

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).

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

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.

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.

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

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

Charming cottage

Simply Serene: Wild West City, 4 acres of privacy

Upstate Modern Scandinavian Barn in the Catskills

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Weekly house rentals

Lower Hudson Valley Idyllic Retreat

Perfect For Families and Large Groups

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

Modern creekside cabin in the Catskills

Billy Joel/JP Morgan Hudson Valley Home 1h to NYC

Arkadia House Mid-century retreat with pool & view

Rustic Swedish Barn/Featured in Airbnb Magazine

Explore a Luxurious Lakefront with Private Beach
Private house rentals

The Hilltop • Fenced 8-Acre Dog-Friendly Retreat

Private Island + Lakefront Home

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

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

Spacious 7BR - Sleeps 12 - LakeVIEW - Fireplace

Farmhouse w/ Sauna & Hot Tub near Storm King

Home in Cold Spring- Farm Stay!

Hudson Valley Hideaway: 10 Minutes to Storm King!
Quick stats about house rentals in Woodbury

Total vacation rentals
Explore 20 vacation rentals in Woodbury

Nightly prices starting at
Woodbury vacation rentals start at $98 CAD per night before taxes and fees

Verified guest reviews
Over 240 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Woodbury vacation 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!
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- Rentals with a firepit Woodbury
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 - Pet-friendly rentals Woodbury
 - Rentals with outdoor seating Woodbury
 - Rentals with a washer and dryer Woodbury
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