
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.

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.

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🐕

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.

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!)

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.

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

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.

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!

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.

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

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.

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
Other great holiday rentals in Woodbury

Gorgeous Suite w/ Private Entrance

Sunset House: near West Point, Hiking & Woodbury

A-Frame Modern House w/ Private Pond

A Cozy-Luxe Getaway | Scenic & Serene

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

Arkadia House Mid-century retreat with pool & view

[Rabbit Hill Cabin] Hiking/Private/Forest view

The cottage at Oasis Cove
When is the best time to visit Woodbury?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°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!
Destinations to explore
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- Times Square
- Madison Square Garden
- New York City Center
- Central Park Zoo
- New York University
- Columbia University
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Barclays Center
- United Nations Headquarters
- Rockefeller Center
- Empire State Building
- Citi Field
- Grand Central Terminal
- Bethel Woods Center for the Arts
- Bryant Park
- Statue of Liberty
- Radio City Music Hall
- Astoria Park
- Thunder Ridge Ski Area
- Fairfield Beach
- USTA Billie Jean King National Tennis Center
- American Dream





