Woodbourne holiday rentals

We found 319 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Woodbourne to find one that's perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include Wi-Fi and a hot tub. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Woodbourne

Showing deals for:4 Dec - 11 Dec

Sun-room with french doors
Property grounds
View from rear of house, standing at sin-room entryway.
Exterior
Exceptional
(39 reviews)

Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

11% off
S$2,120
for 7 nights, 1 cabin
S$303 per night
includes taxes & fees
Waterfront property, perfect winter getaway, directly on the Willowemoc!
Second floor Hallway
The house
Dining table
The fields
Exceptional
(87 reviews)

The Stone Wall Property on 25 acres with private lake

Hurleyville

8% off
S$3,215
for 7 nights, 1 cottage
S$459 per night
includes taxes & fees
The Stone Wall Property on 25 acres with private lake
Pool
Interior
Indoor spa tub
Living area
Exceptional
(41 reviews)

Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Monticello

7% off
S$5,864
for 7 nights, 1 villa
S$838 per night
includes taxes & fees
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!
Living area
Main Cabin- dining, kitchen, fireplace, common area, walk in/out to patio
Interior
Sun Room + screened in porch in summer months
Exceptional
(6 reviews)

NEW Mid Century Expansive Hillside 4-bed nature retreat on 100+ acres

Ellenville

11% off
S$3,685
for 7 nights, 1 room
S$526 per night
includes taxes & fees
NEW Mid Century Expansive Hillside 4-bed nature retreat on 100+ acres
Property grounds
Living area
Living area
Exterior
Exceptional
(46 reviews)

Wood Cabin in Catskill NYS

Woodbourne

11% off
S$6,304
for 7 nights, 1 cabin
S$901 per night
includes taxes & fees
Wood Cabin in Catskill NYS
Pool
Exterior
Exterior
Interior
Exceptional
(7 reviews)

Luxe, Secluded Catskill Lodge Heated Pool, Hot Tub

Ellenville

8% off
S$10,565
for 7 nights, 1 home
S$1,509 per night
includes taxes & fees
Luxe, Secluded Catskill Lodge Heated Pool, Hot Tub
Screen Room
House with Screen Room
Living area
Private Lake Area
Exceptional
(31 reviews)

Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!

Wurtsboro

12% off
S$2,161
for 7 nights, 1 chalet
S$309 per night
includes taxes & fees
Beautiful Chalet with Private Lake Spot Near Popular Resorts - Wurtsboro NY!
Exterior
Property grounds
Interior
Property grounds
Exceptional
(13 reviews)

The Blue House on the Hill Catskills—VIEWS

Claryville

16% off
S$3,123
for 7 nights, 1 home
S$446 per night
includes taxes & fees
The Blue House on the Hill Catskills—VIEWS
Property grounds
Private kitchen
Exterior
Dining
Very good
(28 reviews)

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Monticello

7% off
S$8,333
for 7 nights, 1 home
S$1,190 per night
includes taxes & fees
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
View of home from River
Modern Kitchen
Sitting Room with view of River
Picnic back with old Barn
Exceptional
(15 reviews)

Charming Catskill Farm House on River Front

Woodridge

11% off
S$3,325
for 7 nights, 1 home
S$475 per night
includes taxes & fees
Charming Catskill Farm House on River Front
Interior
Living area
Living area
Private kitchen
Exceptional
(12 reviews)

Manor house renovated with rustic charm

Livingston Manor

7% off
S$2,814
for 7 nights, 1 home
S$402 per night
includes taxes & fees
Manor house renovated with rustic charm
Room
Property grounds
Bar (on property)
Exterior
Exceptional
(57 reviews)

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello

7% off
S$6,432
for 7 nights, 1 home
S$919 per night
includes taxes & fees
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Living room
View upon arrival
BBQ area
Stairways to second floor and lower level
Exceptional
(6 reviews)

Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!

Napanoch

11% off
S$3,388
for 7 nights, 1 home
S$484 per night
includes taxes & fees
Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Woodbourne getaway

Learn about the unique charm of Woodbourne with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Woodbourne

Are you looking for attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Woodbourne has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Concord Monster Golf Course (7 mi / 11.2 km)
  • Sullivan County Golf and Country Club (9.1 mi / 14.6 km)
  • Monticello Motor Club (10.9 mi / 17.6 km)
  • Straus Center - Frost Valley YMCA (15.1 mi / 24.2 km)
  • Brimstone Hill Winery (17.2 mi / 27.6 km)
  • Tarry Brae Golf Course (3.2 mi / 5.1 km)

Exploring the natural landscape of Woodbourne

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Woodbourne. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Sam's Point Preserve (13.1 mi / 21.1 km)
  • Mongaup Pond Campground (14.6 mi / 23.4 km)
  • Woodstock Monument (15.3 mi / 24.7 km)
  • Neversink River (15.4 mi / 24.8 km)
  • Lake Superior State Park (16 mi / 25.8 km)
  • Minnewaska State Park (18.4 mi / 29.6 km)

Transport options to and around Woodbourne

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 31.8 mi (51.1 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Woodbourne?
The most desirable types of holiday rentals in Woodbourne are cabins. Ready for more choices? Vrbo has a variety of options to match our guests' needs, so you'll see properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — grab yours today.
How much does it cost to rent a holiday rental in Woodbourne?
A number of things determine how much you'll pay for a holiday rental in Woodbourne, like the type of property, season and length of stay. Still, all Vrbo homes have something in common — exceptional value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Woodbourne?
Prices for beach houses in Woodbourne will vary depending on the size and style of the property and time of year you're travelling. Simply enter your dates of travel into Vrbo and the number of guests to see your options and prices. From there you can use the filters to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday rentals in Woodbourne?
Good news. There are. Choose from seven holiday homes that roll out the welcome mat in Woodbourne on Vrbo. Our furry friends need a break too, so simply use our search function for pet-friendly holiday rentals to book a perfect pad where your pooch can get in on the family fun.
What are popular rental amenities in Woodbourne?
A barbecue grill, a swimming pool and an electric car charging station are rated the most popular rental amenities in Woodbourne. Whether you're taking to the road by yourself, with your better half or a bunch of friends, Vrbo will help you find a holiday home that fits your style with all the conveniences you're looking for.
Are there large group holiday rentals in Woodbourne?
Take your pick of three Vrbo properties in Woodbourne that can host five or more people. You'll get all the space and privacy you need to spend time with the people you're holidaying with — and no one else.
Are there holiday rentals in Woodbourne that welcome kids?
Woodbourne has seven family-friendly holiday rentals to choose from. And tracking down a stay that welcomes youngsters is super easy with Vrbo's "Properties good for families" filter. As well as having the whole place to yourselves, you'll also enjoy access to perks and amenities like extra bedrooms, private pools and yards.
What are the top attractions for families in Woodbourne?
Keeping the kids entertained during your holiday in Woodbourne is a breeze with these top family-friendly attractions:
  • The Kartrite Resort & Indoor Waterpark
  • Concord Monster Golf Course
  • Tarry Brae Golf Course
Are there one-bedroom holiday rentals in Woodbourne?
Yes, you can choose from two one-bedroom rentals in Woodbourne. Whether you're on the lookout for a secluded cottage or an upmarket condo, Vrbo's one-bedroom properties are just right if you don't need lots of space. One of the best parts about having your own place? You won't need to share your trip with strangers.
Are there holiday rentals with WiFi in Woodbourne?
Pick from three holiday rentals with WiFi in Woodbourne. If you want to disconnect from the world during your break, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Woodbourne?
Pick your travel dates and then use our filter tool to locate holiday rentals with air conditioning in Woodbourne on Vrbo. With five air-conditioned properties on offer here, you can look forward to a cool and comfy stay.
How old do you have to be to rent a holiday rental in Woodbourne?
The minimum age permitted can differ across properties on Vrbo, so check the rules of the holiday rental in Woodbourne you're considering. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Woodbourne for?
It's up to the Woodbourne property. To look at a list of options offering extended stays, just type your dates and guest number into the Vrbo search page. Enjoy having the property to yourself, along with home comforts like air conditioning, a kitchen and a yard to play in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.