Town of Olive Holidays from NZ$2,343

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The Latest Town of Olive Holiday Deals

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was NZ$3,884, price is now NZ$2,343 per person
NZ$2,343
per person
15 Jan - 23 Jan
found 1 hour ago
Return direct flight included
Auckland (AKL) to New York (NYC)
18.4/10 Exceptional! (2,007 reviews)
The staff was very friendly. We were able to leave our luggage before check in and after checkout. Complimentary beverages and refills were provided. I booked through third party and no issues with reservation. We had the family suite which included 2 full beds, 1 king, 2 bathrooms. It was very clean and perfect size for 4 adults.

Reviewed on 14 Nov 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was NZ$11,033, price is now NZ$6,723 per person
NZ$6,723
per person
25 Dec - 1 Jan
found 1 day ago
Return direct flight included
Auckland (AKL) to New York (NYC)
19.2/10 Exceptional! (158 reviews)
A perfect place to stay!!

Reviewed on 20 Sept 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
Price was NZ$4,900, price is now NZ$3,015 per person
NZ$3,015
per person
15 Jan - 23 Jan
found 1 hour ago
Return direct flight included
Auckland (AKL) to New York (NYC)
16.8/10 Exceptional! (1,660 reviews)
The room overlooking the park is absolutely amazing.

Reviewed on 14 Nov 2025

Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
Price was NZ$3,909, price is now NZ$2,463 per person
NZ$2,463
per person
15 Jan - 23 Jan
found 1 hour ago
Return direct flight included
Auckland (AKL) to New York (NYC)
16.4/10 Exceptional! (1,943 reviews)
Rooms left much to be desired. Not a proper placement to room anyone considering rooms were being renovated above which directly affected the plumbing in our room.

Reviewed on 27 Oct 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was NZ$4,258, price is now NZ$2,871 per person
NZ$2,871
per person
15 Jan - 23 Jan
found 1 hour ago
Return direct flight included
Auckland (AKL) to New York (NYC)
18/10 Exceptional! (2,794 reviews)
I was allowed an early check-in which was wonderful! But then the key stopped working and the wifi instructions were unclear.

Reviewed on 14 Nov 2025

Our pick of the best Town of Olive Hotel Deals

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
The price is NZ$209 per night from 1 Dec to 2 Dec
NZ$209
1 Dec - 2 Dec
includes taxes & fees
7.6/10 Good! (1,004 reviews)
Room was clean and comfortable.

Reviewed on 3 Nov 2025

Best Western Plus Kingston Hotel And Conference Center
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
The price is NZ$158 per night from 19 Nov to 20 Nov
NZ$158
19 Nov - 20 Nov
includes taxes & fees
7.6/10 Good! (921 reviews)
It was great for one night .. good location

Reviewed on 8 Nov 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
The price is NZ$1,771 per night from 16 Dec to 17 Dec
NZ$1,771
16 Dec - 17 Dec
includes taxes & fees
9.4/10 Exceptional! (54 reviews)
Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ...

Reviewed on 16 Sept 2025

Wildflower Farms, Auberge Collection
See all 2,148 properties in Town of Olive
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$2,343, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.