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Woodbury Holiday Rentals

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Our top choices for Woodbury holiday rentals

10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$325
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom retreat minutes from West Point!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very cute, well decorated, quiet, and has everything we needed for a get away."
United States
Alexis
The price is NZ$403
includes taxes & fees
5 Jan - 6 Jan 2026
Forava Cabins - Tiny Cabin in the Woods
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is NZ$456
includes taxes & fees
19 Jan - 20 Jan 2026
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
The price is NZ$630
includes taxes & fees
5 Jan - 6 Jan 2026
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (20)
"The location was perfect for our visit and the apartment was immaculately clean and well stocked."
United States
Claudia M.
The price is NZ$324
includes taxes & fees
14 Jan - 15 Jan 2026
Charming Apartment in Quiet Neighborhood
9.4 out of 10, Exceptional, (8)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is NZ$264
includes taxes & fees
5 Jan - 6 Jan 2026
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Aparthotel in Greenwood Lake

Villa Verde B&B, bsm, Greenwood Lake NY
10.0 out of 10, Exceptional, (12)
"The breakfast was lovely!"
United States
Tara
The price is NZ$496
includes taxes & fees
1 Jan - 2 Jan 2026
Villa Verde B&B, bsm, Greenwood Lake NY
9.8 out of 10, Exceptional, (12)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is NZ$501
includes taxes & fees
29 Dec - 30 Dec
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is NZ$469
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is NZ$791
includes taxes & fees
15 Jan - 16 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !
9.6 out of 10, Exceptional, (41)
"Wonderful place! Beautifully decorated, high ceilings, yard, and easy access to the river and cafes. Perfect getaway from the city. Will stay again!"
United States
Emily G.
The price is NZ$444
includes taxes & fees
30 Dec - 31 Dec
Grant - A Tranquil One Bedroom Steps from River
2.0 star property
The price is NZ$431
includes taxes & fees
4 Jan - 5 Jan 2026
Forava Cabin • Tiny Home in the Woods + Sauna
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
The price is NZ$412
includes taxes & fees
4 Jan - 5 Jan 2026
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is NZ$415
includes taxes & fees
7 Jan - 8 Jan 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
9.8 out of 10, Exceptional, (14)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is NZ$478
includes taxes & fees
29 Dec - 30 Dec
Cabin in the heart of the Hudson Valley, Cabin 3
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is NZ$675
includes taxes & fees
5 Jan - 6 Jan 2026
Local Artist Inspired | Walk to WestPoint + King Bed
10.0 out of 10, Exceptional, (33)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is NZ$446
includes taxes & fees
11 Jan - 12 Jan 2026
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
10.0 out of 10, Exceptional, (31)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is NZ$478
includes taxes & fees
1 Jan - 2 Jan 2026
Cabin in the Heart of the Hudson Valley, Cabin 1
10.0 out of 10, Exceptional, (2)
"Very clean and great place to stay. "
United States
Charlene D.
The price is NZ$467
includes taxes & fees
7 Jan - 8 Jan 2026
Lux APT Your home away from home.
9.0 out of 10, Wonderful, (10)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is NZ$442
includes taxes & fees
29 Dec - 30 Dec
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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

Find out more about Woodbury

Everything you need to know about Woodbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodbury holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodbury holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodbury holiday rentals we have selected for you start as low as NZ$264 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 holiday 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 holiday.

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 holiday rentals in Woodbury?

Yes, there are holiday rentals close to the most popular sights in Woodbury, or you can select a more secluded option if you're looking for a relaxing 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 coffee shops.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Woodbury offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with an oven, a microwave and kitchenware, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Woodbury?

Expedia has 3 holiday 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 holiday rentals like in Woodbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodbury. Holiday rentals offer extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for small groups.