Town of Olive Holidays
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Town of Olive Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
S$2,177
per person
4 Oct - 14 Oct
found 4 hours ago
Return flight included
Atlanta (ATL) to New York (JFK)
6.8/10 (2,071 reviews)
The rooms are small which is totally fine. The customer service was not all that great except for the one staff member who actually helped us get a fan. The plumbing was messed up and had no hot water, AC, or ice. And they had no way of saying how long it would be that way. The elevators are very tiny and hold only a couple of people with luggage. Room was clean but other than the one helpful staff member, that was all they had going for them.
Reviewed on 25 Aug, 2026
Ink 48 Hotel
Manhattan
S$2,666
per person
8 Oct - 18 Oct
found 4 hours ago
Return direct flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very good! (1,755 reviews)
You have to pay a resort fee of $40 which really isn't worth much if you're not using the gym etc. Didn't have a chance to check out the rooftop bar since there was a monsoon the night I was there! The location is good. Easy walk to Broadway.
Reviewed on 26 Aug, 2026
Margaritaville Resort Times Square
Manhattan
S$2,901
per person
3 Oct - 13 Oct
found 1 day ago
Return flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (4,286 reviews)
Really clean room and totally sound proofed! Slept so so well! The staff I met were very helpful. Great location. The pity for me was the pool, which was my reason for booking the hotel. It’s a lot smaller than it looks and was so busy I couldn’t get in it!
Reviewed on 26 Aug, 2026
The Ridge Hotel
Manhattan
S$2,351
per person
2 Oct - 12 Oct
found 1 day ago
Return flight included
Atlanta (ATL) to New York (JFK)
8.2/10 Very good! (1,193 reviews)
Good value, bed was comfortable, the room had everything we needed, good location, the roof top has a cool view. Could have been cleaner and the elevator was slow at check-in due to being used by housekeeping. Staff was pleasant, but pretty hands-off.
Reviewed on 26 Aug, 2026
Top hotels in Town of Olive
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
S$231
20 Sept - 21 Sept
includes taxes & fees
8.2/10 Very good! (987 reviews)
"I have a habit of calling ahead a day or two before my arrival to make sure my reservation is confirmed. I made numerous attempts to to so and no one was answering the phones? It took from 1.30pm - 8.30pm to reach someone.... Other than the trash can missed being empty, all was very nice. I will ..."
Reviewed on 26 Aug, 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
S$201
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"Hunter Lodge is a pleasant, no frills stay for a reasonable price. The rooms are clean and the mountain view is lovely. Breakfasts are simple and basic. Sadly, breakfast upkeep and clean up is disappointing."
Reviewed on 27 Aug, 2026
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
S$127
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 holiday package cost?
Starting from only S$2,177, 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
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.
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.
* 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.
