Town of Olive Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Town of Olive Holiday
Leave all the planning up to us with a Town of Olive holiday package. With everything arranged before you leave, the only thing you'll need to do is relax and experience this destination's culture and beauty. With so much to see and do on a trip to Town of Olive, it can be difficult to know where to begin. Kick off your travels in West Shokan at Catskill Mountains and Giant Ledge Trailhead — two popular attractions here. Another great city to add to your itinerary is Olivebridge. Be sure not to miss Woodstock Public Library and Woodstock Golf Club. Expedia has hotels, flights and whatever else you need to help you create your very own tailored Town of Olive holiday today.
Top Town of Olive Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Town of Olive Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | John F. Kennedy Intl. Airport (JFK) |
Top hotels in Town of Olive
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
£134
30 Aug - 31 Aug
includes taxes & fees
8.2/10 Very good! (984 reviews)
"Very nice walk through history in this gorgeous Inn. Centrally located and walkable to all the town has to offer. I loved the room - so nicely appointed - even included sherry! The towels even had a lavender smell to them which was a nice touch."
Reviewed on 21 Aug 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
£106
10 Sept - 11 Sept
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"Great property in the Catskills! Convenient to many hikes and cute towns! Room with the loft was perfect for our family of three. Definitely recommend!"
Reviewed on 21 Aug 2026
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
£73
31 Aug - 1 Sept
includes taxes & fees
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.
Frequently asked questions
How much does a Town of Olive travel package cost?
Starting from only £452, a travel package is your gateway to cheaper travel. Customize your Town of Olive trip by picking from our wide range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Town of Olive travel package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Locked in your Town of Olive travel package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may be charged a fee by your hotel, airline or car rental company. For more information, look up our Customer Service Portal. We're here to help you each step of the way.
How do I get a cheap travel package to Town of Olive?
It's easy. Just bundle everything together. Hotels, rental cars and flights — combine whatever you need into a Town of Olive travel package to save a pile of cash. Score even better deals when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your own way. We offer more than 550 airlines and 1,000,000 hotel options worldwide, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Town of Olive holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fabulous getaway without draining your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Consider one of these flexible payment options:
- Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all budgets, so you can lock in that well-earned holiday sooner.
- Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.
What are the top hotels in Town of Olive?
Best Western Plus Kingston Hotel And Conference Centre and Howard Johnson by Wyndham Saugerties are a couple of the most popular properties in Town of Olive. Why not check out the facilities and amenities at each and then make a decision?
How far in advance should I book my Town of Olive holiday?
It can be hard to know exactly when is the ideal time to book your Town of Olive holiday. But usually the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels up to 12 months before your departure date. If you're eager to escape on a last-minute getaway, no need to fret! There are terrific deals popping up on Expedia every day.
What does an Expedia Town of Olive travel package include?
With Expedia, you can choose any combination of hotels, car rentals and flights to build your perfect Town of Olive package. Once you've made your booking, you can add on the fun stuff like tours and activities. Don't forget, the more you bundle, the more you'll save!
What should I know before booking a Town of Olive travel package?
You can save a tidy sum by bundling your flights, hotels and rental cars. Once you've created your package, add on fun stuff like tours and activities. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Town of Olive Expedia travel package?
You can, and with over 550 airlines to select from all over the world, you're not short on choice. Look through the available options and find out which airline suits your budget and needs.
Stay near popular Town of Olive attractions
Olive Free Library
After visiting Olive Free Library, make a plan to see the other sights and activities in West Shokan. Discover the mountain views while you're in the area.
Brown's Station
Explore the great outdoors at Brown's Station, a lovely green space in Olivebridge. Amble around the area's forests or experience its entertainment choices.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
