Holiday houses in Woodbury

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Top-rated holiday rentals in Woodbury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Place to stay in Warwick
4.96 out of 5 average rating, 366 reviews

Luxe Penthouse Studio MainSt Warwick, SteamShower!

Relax & Indulge in our Luxe Penthouse Studio with Elevator & Parking! Beautifully furnished on Main St. in Warwick- Walk to Everything! Panoramic windows with amazing views over Warwick. Spa steam shower with bluetooth speakers, luxury bath toiletries, Heavenly King bed with Egyptian cotton linens, 65 in. HD Smart TV, reclining leather theater seats, velvet loungers convert into sleepers, fully stocked designer kitchen with all appliances, Nespresso & Keurig, coffee, tea, bottled water included.

Guest favourite
A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.
Cottage in Monroe
4.98 out of 5 average rating, 192 reviews

Cozy Lake Cottage

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets in any temps from inside or out, or coffee in the tree hut! Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

Top Guest favourite
A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.
Home in Staatsburg
4.99 out of 5 average rating, 127 reviews

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.

Top Guest favourite
A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.
Cabin in Greenwood Lake
4.96 out of 5 average rating, 477 reviews

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Guest favourite
A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.
Guest suite in Chester
4.95 out of 5 average rating, 380 reviews

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–6 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.98 out of 5 average rating, 381 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top Guest favourite
Guest suite in New Windsor
4.96 out of 5 average rating, 275 reviews

Hudson Valley Spacious Studio Private Secure

Soak in the heated Jacuzzi bathtub Enjoy home-baked muffins and cookies This Spacious studio is an intimate setting for couples Roomy enough for 2 friends to share West Point parents/your cadet stays free Single traveler discount Welcome basket - Home-baked goodies 2 Super comfy queen beds Luxurious bathroom/heated Jacuzzi bath/seated walk in shower Desk/Wifi Private parking/entrance 42 inch tv Coffee/tea/condiments SKAC USMA Woodbury Common DIA Beacon Hiking -No cooking allowed.

Guest favourite
Apartment in Newburgh
4.89 out of 5 average rating, 256 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top Guest favourite
A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.
Home in Greenwood Lake
5 out of 5 average rating, 216 reviews

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.

Top Guest favourite
A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.
Treehouse in Wallkill
4.99 out of 5 average rating, 380 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Guest favourite
A serene lakeside view is captured, featuring lush greenery and colorful plants in planters. A lounge chair is positioned on the grass, inviting relaxation while looking out over the calm waters of the lake, framed by a backdrop of tree-covered hills.
Cottage in Monroe
4.95 out of 5 average rating, 110 reviews

Hudson Valley Lakefront Cottage | Nature Escape

Escape to this tranquil, lakefront cottage in the Hudson Valley. Enjoy stunning lake and cascading creek views, kayaks, paddleboards, a firepit with a steady supply of firewood for cozy evening fires, two Weber grills, and an on-site Level 2 EV charger. Ideal for couples, small groups, or intimate gatherings seeking a peaceful retreat surrounded by nature.

Top Guest favourite
A mid-century octagonal house is surrounded by lush greenery, featuring large glass windows that offer generous natural light. A wooden deck extends from the entry, framed by a black railing. The serene hilltop location provides a peaceful retreat in nature.
Home in New Windsor
4.92 out of 5 average rating, 145 reviews

View House

Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.

Popular amenities for Woodbury holiday rentals

When is the best time to visit Woodbury?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$208 AUD$220 AUD$249 AUD$423 AUD$281 AUD$286 AUD$423 AUD$415 AUD$423 AUD$330 AUD$570 AUD$267 AUD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Woodbury?

    Woodbury has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Woodbury?

    Experience the best of Woodbury with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Woodbury?

    Four-legged friends are welcome in Woodbury. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Woodbury?

    Yes! Work meets play with ease at over 30 vacation rentals in Woodbury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Woodbury vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Woodbury, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Woodbury?

    Make yourself at home in Woodbury by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Central Valley, over 110 vacation rentals in Highland Mills, and over 30 vacation rentals in Harriman.

  • Do house rentals in Woodbury have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Woodbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodbury have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Woodbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodbury have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Woodbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodbury have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Woodbury. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Woodbury

  • Total holiday rentals

    Explore 50 holiday rentals in Woodbury

  • Nightly prices starting at

    Woodbury holiday rentals start at $97 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,350 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Woodbury holiday rentals include Wi-Fi 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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