Town of Olive Vacations & Trips from ￥294,156

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to ￥45,448 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

The Latest Town of Olive Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was ￥402,894, price is now ￥294,156 per person
￥294,156
per person
Dec 4 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to New York (JFK)
8/10 Very Good! (2,198 reviews)
This hotel is a hidden gem. Clean rooms, friendly staff, and a fantastic location. I was able to walk to most attractions. I also appreciated how quickly they responded to requests

Reviewed on Oct 21, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥492,167, price is now ￥310,851 per person
￥310,851
per person
Dec 7 - Dec 11
found 16 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (2,748 reviews)
Great options! Stay here often

Reviewed on Oct 21, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was ￥661,624, price is now ￥476,628 per person
￥476,628
per person
Dec 28 - Jan 1
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (1,008 reviews)
My fav spot in all of NYC!

Reviewed on Oct 11, 2025

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was ￥460,370, price is now ￥337,905 per person
￥337,905
per person
Dec 4 - Dec 8
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to New York (JFK)
8.4/10 Very Good! (1,438 reviews)
The staff was efficient, helpful, friendly and informative. I will definitely be staying her for future trips to the city.

Reviewed on Oct 19, 2025

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Price was ￥819,630, price is now ￥608,402 per person
￥608,402
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (1,018 reviews)
Clean, comfortable, & great location!

Reviewed on Oct 22, 2025

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 ￥17,182 per night from Oct 28 to Oct 29
￥17,182
￥19,243 total
Oct 28 - Oct 29
includes taxes & fees
7.6/10 Good! (1,036 reviews)
For all the goods, the property seems to be in transition and I can't tell if it's going to get better or worse.

Reviewed on Oct 17, 2025

Best Western Plus Kingston Hotel And Conference Center
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is ￥166,117 per night from Nov 12 to Nov 13
￥166,117
￥192,612 total
Nov 12 - Nov 13
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 Sep 16, 2025

Wildflower Farms, Auberge Collection
Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
7 Terwilliger Ln, New Paltz, NY
Fully refundableReserve now, pay when you stay
The price is ￥14,287 per night from Nov 6 to Nov 7
￥14,287
￥16,000 total
Nov 6 - Nov 7
includes taxes & fees
8.8/10 Excellent! (1,022 reviews)
Great place for a stay on the way!

Reviewed on Oct 16, 2025

Americas Best Value Inn New Paltz
See all 2,140 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 vacation package cost?
Starting from only ￥294,156, a vacation 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 vacation 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 travelers.
How far in advance should I book my Town of Olive vacation?
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 traveling 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 organizing 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 vacation 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 vacation package?
Your situation can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Olive vacation 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.