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Woodbury Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Woodbury holiday rentals

Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is HK$1,434
HK$4,035 total
includes taxes & fees
28 Jun - 29 Jun
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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)
The price is HK$952
HK$1,503 total
includes taxes & fees
22 Jun - 23 Jun
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,324
HK$2,166 total
includes taxes & fees
22 Jun - 23 Jun
Cabin in the heart of the Hudson Valley, Cabin 3
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,763
HK$3,317 total
includes taxes & fees
22 Jun - 23 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, (34 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,324
HK$2,166 total
includes taxes & fees
22 Jun - 23 Jun
Cabin in the Heart of the Hudson Valley, Cabin 1
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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is HK$1,552
HK$2,564 total
includes taxes & fees
22 Jun - 23 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is HK$2,645
HK$4,180 total
includes taxes & fees
22 Jun - 23 Jun
Modern penthouse suite in a restored grain tower with private roof deck.
Fridge, microwave, oven, stovetop

Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is HK$2,118
HK$3,756 total
includes taxes & fees
22 Jun - 23 Jun
Luxury 3BR with King Beds in Montgomery Village
Private kitchen

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is HK$3,449
HK$4,247 total
includes taxes & fees
13 Jul - 14 Jul
Carriage House Apartment Goshen NY
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 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$1,380
HK$2,270 total
includes taxes & fees
22 Jun - 23 Jun
Historic Cabin with Pool & Fire Pit
Interior

Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is HK$2,688
HK$5,469 total
includes taxes & fees
25 Jun - 26 Jun
Bright Cornwall-on-hudson Vacation Rental!
Smart TV, fireplace

Charming 2-bedroom cabin with a stunning view

Charming 2-bedroom cabin with a stunning view
Vernon Township
10.0 out of 10, Exceptional, (8 reviews)
"A beautiful home! And incredible lake views. We loved our stay here"
United States
Ellie H.
The price is HK$3,135
HK$4,016 total
includes taxes & fees
25 Jun - 26 Jun
Charming 2-bedroom cabin with a stunning view
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (38 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is HK$1,675
HK$4,129 total
includes taxes & fees
22 Jun - 23 Jun
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is HK$3,879
HK$5,505 total
includes taxes & fees
22 Jun - 23 Jun
Chestnut on Willow Lake
Interior

Harriman Outdoor Center - White Oak Cabin

Harriman Outdoor Center - White Oak Cabin
Haverstraw
The price is HK$1,889
HK$2,168 total
includes taxes & fees
24 Jun - 25 Jun
Harriman Outdoor Center - White Oak Cabin
Outdoor spa tub

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (9 reviews)
"So cute and cozy!! We had the best time and loved it. "
United States
corinne n.
The price is HK$1,983
HK$3,777 total
includes taxes & fees
23 Jun - 24 Jun
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Exterior

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248
Vernon
10.0 out of 10, Exceptional, (12 reviews)
"Me, my partner and another couple stayed here for a summer weekend, the accommodations were so cozy, everything provided was great! The kitchen was fully equipped and we had pleasant breakfasts in the mornings, we went for the waterpark right around the corner, and we hope to return for the winter season. We all loved the stay! "
United States
David C.
The price is HK$2,069
HK$4,003 total
includes taxes & fees
25 Jun - 26 Jun
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248
Fridge, microwave, stovetop, dishwasher

Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful place, safe neighborhood, very clean and cozy. "
United States
Glori B.
Bright Cornwall-On-Hudson Vacation Rental!
Private kitchen

2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (1 review)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
The price is HK$1,481
HK$1,897 total
includes taxes & fees
1 Jul - 2 Jul
2-bedroom apartment in excellent Newburgh with AC and charm
Free WiFi, bed sheets

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.6 out of 10, (7 reviews)
"It was a great place "
United States
Jose
The price is HK$984
HK$2,133 total
includes taxes & fees
2 Jul - 3 Jul
Cottage Suites
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

Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Good"
Ayellen 1-night trip
Posted 8 hours ago
Inn on the Hudson

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, we have holiday rentals where you'll be just 10.7 mi (17.3 km) from LEGOLAND® New York, giving you a secluded option if you want a quiet 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 coffee shops.

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

Lakefront Paradise Pool + Paddle Boats Sleeps 12: This holiday home rental outside of Woodbury offers an outdoor pool, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of garden in this rental home to help you unwind.

How many holiday rentals will I find in Woodbury?

Expedia has 6 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.