
House holiday rentals in Woodbury
Find and book unique houses on Airbnb
Top-rated house rentals in Woodbury
Guests agree: these houses are highly rated for location, cleanliness and more.

Slate Cabin - Stylish Country Escape x Rhinebeck
This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.
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.

Modern 3BD West Point USMA House w/ HotTub!
Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

Your West Point Academy Home Away from Home
Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

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.

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

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.

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Balmville Mid-Century Gem & Work From Home Retreat
Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

Spacious, bright 5 bedroom house near West Point
Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

4 Bd Paradise Gorgeous Design Close to All!
Forget your worries in this spacious and serene space. The Riley house is close to Stewart Airport, West Point, NYMA, The Storm King School and Mount Saint Mary College and all the Hudson Valley has to offer. Central to Wallkill, Patterson, and Warwick as well. Extra fees will apply for guests over 6 and pets.
Popular amenities for house rentals in Woodbury
House rentals with a pool

TheGoshenGetawayPoolHotTubLegoLandArcade.

Entire Home (private pool), Event Friendly

Private Retreat w/Pool, Hot Tub & Fire Pit, 6 BR

Scenic River View Escape | New Paltz

4Br Mountain Brook House on 130 acres w/ trails

Mountain Creek retreat PH w/pool & hot tub

Charming cottage

New Paltz dog friendly retreat w/ salt water pool
Weekly house rentals

Sunset House: near West Point, Hiking & Woodbury

World Cup Base ~ Lakefront House w/ Hot Tub & View

Mountainside Home (Beacon/Cold Spring)

Arkadia House Mid-century retreat with pool & view

Hot Tub Bliss on 2 acres 16mi to West Point

Rustic Swedish Barn/Featured in Airbnb Magazine

Home in Cold Spring- Farm Stay!

Modern, sun-filled farmhouse retreat
Private house rentals

The Hilltop • Fenced 8-Acre Dog-Friendly Retreat

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

On the Lake - 5 Kings - Huge Yard - Massage Chair

Deer Pond Lodge 4BR Hot Tub & Game Room Pet

Elegant Hideaway: Cozy Cottage in Katonah, NY

Victorian Eclectic

Cold Spring Hidden Gem: woods, walk to town, SAUNA

Hudson Valley Getaway/West Point/Woodbury/Legoland
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 $102 SGD per night before taxes and fees

Verified guest reviews
Over 400 verified reviews to help you choose

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

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!
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- Family-friendly rentals Woodbury
- Rentals with a washing machine and dryer Woodbury
- Rentals with a firepit Woodbury
- Rentals with outdoor seating Woodbury
- Pet-friendly rentals Woodbury
- Rentals with a fireplace Woodbury
- Rentals with pools Woodbury
- Rentals with a patio Woodbury
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