Town of Olive Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Town of Olive Flight & Hotel Packages

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

Radio Hotel

4 out of 5
Manhattan
Price was S$1,843, price is now S$1,343 per person
S$1,343
per person
27 Dec - 29 Dec
found 15 hours ago
Return direct flight included
London (LON) to New York (NYC)
17.2/10 Exceptional! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on 22 Nov, 2025

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was S$2,323, price is now S$1,523 per person
S$1,523
per person
27 Dec - 29 Dec
found 15 hours ago
Return direct flight included
London (LON) to New York (NYC)
18.4/10 Exceptional! (3,941 reviews)
I will only stay here in NY from now on. Clean, new, well furnished, spacious rooms. Great options for food. Reasonably priced. Great location, quiet. Cool roof decks. Friendly staff!

Reviewed on 23 Nov, 2025

Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
Manhattan
Price was S$2,158, price is now S$1,594 per person
S$1,594
per person
27 Dec - 29 Dec
found 15 hours ago
Return direct flight included
London (LON) to New York (NYC)
16.8/10 Exceptional! (4,710 reviews)
Nice people, great location, great price

Reviewed on 23 Nov, 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
Price was S$2,144, price is now S$1,599 per person
S$1,599
per person
27 Dec - 29 Dec
found 15 hours ago
Return direct flight included
London (LON) to New York (NYC)
16.8/10 Exceptional! (3,104 reviews)
Room was very nice and clean , wish I could have stayed longer

Reviewed on 23 Nov, 2025

Roxy Hotel New York

Roxy Hotel New York

4.5 out of 5
Manhattan
Price was S$2,038, price is now S$1,531 per person
S$1,531
per person
27 Dec - 29 Dec
found 15 hours ago
Return direct flight included
London (LON) to New York (JFK)
18.8/10 Exceptional! (1,339 reviews)
I really love this hotel. The bed was so soft. All the amenities were great and the staff was extremely friendly. I will be back.

Reviewed on 19 Nov, 2025

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Frequently asked questions

How much does a Town of Olive holiday package cost?
Starting from only S$1,343, 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.