Woodbury Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Woodbury holiday rentals

Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (64 reviews)
"For us it was in a great location, had a reasonable price and room for everyone."
United States
Gertrude (Gert) P.
The price is HK$1,939
HK$2,531 total
includes taxes & fees
7 May - 8 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is HK$1,010
HK$1,564 total
includes taxes & fees
7 May - 8 May
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,689
HK$4,264 total
includes taxes & fees
10 May - 11 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$838
HK$1,656 total
includes taxes & fees
10 May - 11 May
Historic Cabin with Pool & Fire Pit
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$847
HK$1,625 total
includes taxes & fees
6 May - 7 May
Cozy 1-bedroom retreat minutes from West Point!
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is HK$901
HK$2,404 total
includes taxes & fees
7 May - 8 May
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (135 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,473
HK$2,489 total
includes taxes & fees
10 May - 11 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$979
HK$3,046 total
includes taxes & fees
6 May - 7 May
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (33 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,958
HK$3,467 total
includes taxes & fees
31 May - 1 Jun
Contemporary Cozy Cottage
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,324
HK$2,184 total
includes taxes & fees
7 May - 8 May
Cabin in the Heart of the Hudson Valley, Cabin 1
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is HK$1,163
HK$2,284 total
includes taxes & fees
9 May - 10 May
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Outdoor spa tub

Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (62 reviews)
"Very good host "
United States
Binyomin
The price is HK$2,025
HK$3,840 total
includes taxes & fees
6 May - 7 May
Country House w/Hot Tub, Deck, Grill & Fire Pit
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (17 reviews)
"Great place to stay! "
United States
Megan D.
The price is HK$956
HK$1,666 total
includes taxes & fees
19 May - 20 May
Piermont Oasis
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (16 reviews)
"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 HK$649
HK$1,159 total
includes taxes & fees
6 May - 7 May
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is HK$1,559
HK$1,867 total
includes taxes & fees
6 May - 7 May
Luxury home near West Point
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"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 HK$1,136
HK$3,586 total
includes taxes & fees
6 May - 7 May
Sleek Escape: Modern 3 BR- 4 Min from West Point !
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is HK$1,567
HK$2,543 total
includes taxes & fees
7 May - 8 May
Luxury House Near West Point
Fridge, microwave, oven, stovetop

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

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is HK$1,497
HK$2,567 total
includes taxes & fees
6 May - 7 May
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very good, (6 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is HK$1,183
HK$3,811 total
includes taxes & fees
6 May - 7 May
3BR West Point Retreat-3min to Back Gate+ King Bed
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Such a cute place to stay"
United States
Melissa
The price is HK$1,175
HK$2,295 total
includes taxes & fees
7 May - 8 May
Cozy country efficiency in the Hudson Valley
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

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

8/10 Good
"Staff was wonderful , very clean hotel"
Edna 1-night trip
Posted 6 hours ago
Fairfield Inn & Suites by Marriott Goshen Middletown

Find out more about Woodbury

Search for holiday rentals in Woodbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodbury using one of the methods below:

  • View our selection of featured holiday rentals in Woodbury
  • Use the map to find apartments and other holiday homes in the Woodbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodbury while they last

Look no further and take a look at our great range of rental properties in Woodbury!

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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Woodbury is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

How many holiday rentals will I find in Woodbury?

Expedia has 4 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.