Town of Olive Holidays from NZ$4,080
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The Latest Town of Olive Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square
Manhattan
NZ$4,870
per person
5 Oct - 12 Oct
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (4,305 reviews)
The space was clean, however it took forever to get anywhere. The elevator took a long time and was always packed so getting in and out with luggage was a nightmare. The lobby was on the 6th floor to check in. There was no one to greet you upon arrival. The city parking garage near the hotel wouldn’t allow me access to my car during the day so I chose a different garage that allowed me access but then that became a problem. We ended up having to lug bags through Times Square and then the hotel wouldn’t validate the parking. The pool closed at 8 pm and there was not a lot of pace to sit. The lifeguard was in charge of cleaning up towels people left and getting towels for people so they didn’t always have eyes on the pool. The woman at the desk when I arrived was less than friendly. I wouldn’t go back ever again.
Reviewed on 21 Aug 2026
The Shelburne Sonesta New York
Manhattan
NZ$4,616
per person
5 Oct - 12 Oct
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (2,029 reviews)
Great location! I loved the stay but our air conditioning was leaking water the whole time. So the floor was always wet. Otherwise- great hotel, great location and I would stay there again!
Reviewed on 20 Aug 2026
Our pick of the best Town of Olive Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
NZ$322
31 Aug - 1 Sept
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
NZ$266
7 Sept - 8 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
NZ$167
21 Sept - 22 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 holiday package cost?
Starting from only NZ$4,080, a holiday package is your portal to inexpensive travel. Create your own Town of Olive escape by choosing from our wide range of flights, hotels and rental cars.
How do I get a cheap travel package to Town of Olive?
Book everything all in one place with our Town of Olive holiday packages. You'll find deals on flights, hotels, tours and more that'll keep your hip pocket happy and your adventurous spirit full. And, with more than 550 partner airlines and 1 000 000 hotels all over the world to select from, you have countless opportunities to mix and match all you want.
What are the top hotels in Town of Olive?
If it's your first time staying in Town of Olive, make a reservation at Catskills Family Hideaway or Mountain Retreat With 2 Hot Tubs. Both hotels offer friendly service and are top options with many savvy travellers.
How far in advance should I book my Town of Olive holiday?
While prices do change, we generally suggest booking your seats as soon as possible. Most international airfares become available on Expedia up to 12 months in advance. If you're booking last minute, you might still get lucky. Discount prices to Town of Olive sometimes emerge only weeks before departure.
What does an Expedia Town of Olive travel package include?
It comes down to what you're after. If you're travelling by yourself, you might decide to bundle flights and hotels. Bringing the whole family to Town of Olive? A travel package that includes hotels, rental cars and flights might be a better fit. Expedia gives you the flexibility and freedom to build your own travel package.
What should I know before booking a Town of Olive travel package?
When you book your flights, hotels and car rentals together, you'll be rewarded with great discounts. Whether you're organising a wilderness getaway in a cabin or want to stay in a convenient hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Town of Olive Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to pick from across the world. With all that choice, finding the perfect carrier to whisk you off to Town of Olive won't be difficult.
If I'm not able to travel, can I cancel my Town of Olive holiday package?
Your situation can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Olive holiday package for free if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your airline, hotel or car rental company may impose a charge. Want more information? Have a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
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.
