Woodbourne Vacations from $332

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Your Woodbourne Vacation

Take the hard work out of travel planning with a Woodbourne vacation package. A good neighborhood to base yourself in this amazing city is Greenfield Park, which is good for camping and a lot more. Any trip to Woodbourne needs a well-planned itinerary. Fill yours with leading attractions like Sullivan County Dramatic Workshop - Rivoli Theatre, Tarry Brae Golf Course and Neversink Dam. A few clicks is all it takes to create a customized Woodbourne vacation on Expedia.

The Latest Woodbourne vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $620, price is now $332 per person
$332
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Nice boutique hotel. Convenient location, very clean, but LOUD. No fault of the hotel, but 45th is busy at all hours of the night. Sirens, horns, cars, people, and all other noises makes it impossible to sleep. Bed was extremely hard.

Reviewed on Dec 31, 2025

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,691, price is now $783 per person
$783
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $1,204, price is now $613 per person
$613
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $747, price is now $390 per person
$390
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.6/10 Excellent! (590 reviews)
Great view but a gas station has a better breakfast.

Reviewed on Dec 26, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $759, price is now $402 per person
$402
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Staff were wonderful. Hotel was a great experience

Reviewed on Dec 25, 2025

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Woodbourne Hotel Deals

Log Cabin in Catskill NYS

Log Cabin in Catskill NYS

Woodbourne NY
9.8/10 Exceptional! (46 reviews)
Cozy cabin, good to relax with friends

Reviewed on Oct 13, 2025

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Log Cabin in Catskill NYS
Private Lakeside Paradise - Pool/2Hot tub/Sauna/RV/Pickleball/Basketball

Private Lakeside Paradise - Pool/2Hot tub/Sauna/RV/Pickleball/Basketball

Woodbourne NY
8.6/10 Excellent! (3 reviews)
Nice place. !

Reviewed on Sep 28, 2025

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Private Lakeside Paradise - Pool/2Hot tub/Sauna/RV/Pickleball/Basketball
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive Monticello NY
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $244 total per night from Jan 8 to Jan 9
$244 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8/10 Very Good! (1,884 reviews)
the room was spotless , very nice & clean resort . Staff was very accommodating. This is an amazing place for family especially kids . I would definitely come back !

Reviewed on Dec 27, 2025

The Kartrite Resort & Indoor Waterpark
See all 1,088 properties in Woodbourne
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.

Find the Best Woodbourne Vacation Packages

Woodbourne Essential Information

Language
English
Currency
U.S dollars
Top Sights
The Kartrite Resort & Indoor Waterpark, Holiday Mountain Ski and Fun Park and Sullivan County Dramatic Workshop - Rivoli Theatre

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Frequently asked questions

How much does a Woodbourne vacation package cost?
Offering great value package deals from $332 on Expedia, you'll be surprised at how little a vacation to Woodbourne costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Woodbourne?
If you'd like to score a cheap Woodbourne vacation package, consider planning a trip in January, March and December. You'll generally find lower rates on accommodations and flights during these months — ideal for travelers wishing to save money.
How many days is enough for Woodbourne?
With a well-organized itinerary, you can easily tick off the most popular Woodbourne attractions in a handful of days. But if you want to discover hidden spots or go on day tours, consider booking your Woodbourne vacation for longer.
How to find the best Woodbourne package deals?
Use Expedia's filters to find some tempting Woodbourne package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Woodbourne package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woodbourne vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Woodbourne vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Woodbourne?
If you're considering a spontaneous Woodbourne vacation, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Woodbourne vacation packages?
Jet off on your perfect escape to Woodbourne with help from our Book Now, Pay Later vacations. No need to save like crazy or wait until payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.