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A lakeside park with autumn foliage, a wooden dock, and a picnic area.

Woodbury Vacation Rentals

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  • Check prices for these dates

    Check prices for these dates, December 14–15, 2026

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    Our top choices for Woodbury vacation rentals

    1. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

    A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

    2. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

    A house with a view of a bridge and mountains.

    3. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

    A deck with Adirondack chairs, a fire pit, and a grill.

    4. Cozy 1-bedroom retreat minutes from West Point!

    Living area

    5. Local Artist Inspired | Walk to WestPoint + King Bed

    A modern kitchen with stainless steel appliances, white cabinetry, a coffee station, and a dining area with a wooden table and bench.

    6. Hudson Valley Retreat w/ Pool Near Greenwood Lake

    A backyard with a pool, a gazebo, and a small shed.

    7. 3BR Near West Point | Coffee Bar | Sleeps 6

    A hallway with a wooden door, a black table with a sign, and large green plants.

    8. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

    A brick building with a sign reading 'Lobby' in front.

    9. Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

    A brick building with a storefront featuring a sign for 'LUXE Optique'.

    10. Columbus Suites

    A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

    11. 1 King Bed | Non-Smoking, Kitchen, Shower

    A compact kitchenette with a microwave, stove, sink, and a small dining area.

    12. Grant - A Tranquil One Bedroom Steps from River

    A living room with a dark blue sectional sofa, a round coffee table, and a decorative ceiling light.

    13. Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

    A bathroom with a black vanity, a glass bowl sink, and a mirror above it.

    14. Historic Cabin with Pool & Fire Pit

    A swimming pool with a wooden deck, lounge chairs, and a red umbrella.

    15. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

    A kitchen with black cabinets, a wooden countertop, a black refrigerator, and a window with a view of trees.

    16. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

    A hotel room with a large bed, a TV, a sofa, a desk, and a view of the outside.

    17. A Cozy Private Suite in a Country Home near New Paltz

    A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

    18. Walk to WP Gate + Free Parking!

    A two-story house with a porch and a gated driveway.

    19. Lovely 3BR Home with parking-Walk to WP Gate!

    A room with hardwood flooring, a flat-screen TV on a stand, a white door, and a staircase leading to another level.

    20. Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

    A brick building with a storefront featuring a sign for 'LUXE Optique'.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Top Woodbury Hotel Reviews

    Sleep Inn & Suites Monroe - Woodbury

    A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

    Cromwell Manor Inn

    A large, two-story house with a blue roof, surrounded by lush greenery and a well-maintained lawn.

    The Dominion House Bed & Breakfast

    A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

    La Quinta Inn & Suites by Wyndham Middletown-Goshen

    A modern hotel building with a prominent sign, a covered entrance, and a parking area.

    Candlewood Suites Middletown Goshen by IHG

    A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

    The Abbey Inn & Spa

    A conference room with a stone wall, a large arched window, and a television on the wall.

    Homewood Suites Stewart Airport

    A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

    Residence Inn by Marriott Middletown Goshen

    An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

    Residence Inn by Marriott Fishkill

    An outdoor patio with a stone fire pit surrounded by wicker chairs and a table.

    Harvest Inn

    A spacious hotel lobby with a high ceiling, wooden beams, a large mural, and a seating area with a sofa and chairs.

    Find out more about Woodbury

    Everything you need to know about Woodbury vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodbury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodbury vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Woodbury vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Woodbury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodbury vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Woodbury vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Woodbury rentals

    At Expedia, we put the best Woodbury vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Woodbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodbury vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find vacation rentals in Woodbury?

    Yes, you can find vacation rentals close to the most popular attractions in Woodbury, or you can choose a more remote option if you want a relaxing place to stay. Discover why Woodbury is known for its array of shops and mountain landscape. While you're here, grab a bite or have a drink at the coffeehouses.

    What are some of the best vacation home rentals that Woodbury has to offer?

    Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental near Woodbury is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

    How many vacation rentals will I find in Woodbury?

    Expedia has 6 vacation rentals for your stay in Woodbury.

    What can I see and do in Woodbury?

    Cultural attractions include United States Military Academy, whereas Lake Tiorati Beach is a spot to enjoy nature. While here, Woodbury Common Premium Outlets and Harriman State Park are other places worth a visit.

    What are vacation rentals like in Woodbury?

    Vacation rentals are privately owned accommodations you can reserve for several days or longer in Woodbury. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family getaway.

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