Town of Olive Vacations & Trips from ￥295,022

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The Latest Town of Olive Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was ￥407,830, price is now ￥295,022 per person
￥295,022
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,755 reviews)
Yes and easy to get around

Reviewed on Mar 9, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥1,227,177, price is now ￥780,592 per person
￥780,592
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready.

Reviewed on Feb 24, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥521,913, price is now ￥340,464 per person
￥340,464
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,419 reviews)
Excellent location & staff very helpful. Only drawback was elevators. Early mornings there was only 1 operating in mornings from 6-10:00am. They used other 2 to transport people to 5th floor.(restaurant location.). Had to walk down 12 flights to make my breakfast reservation. Couldn’t get on the one elevator that was available.

Reviewed on Mar 9, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥481,160, price is now ￥321,258 per person
￥321,258
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,923 reviews)
Great location, clean, courteous staff, breakfast buffet had lots of options. Would definately stay again.

Reviewed on Mar 5, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was ￥421,363, price is now ￥310,440 per person
￥310,440
per person
May 22 - May 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
La ubicación se me hizo adecuada ya que es céntrica, está cerca el times square, y a dos cuadras el metro. Hay tiendas de 24 horas muy cerca. La habitación la entregaron limpia y también hacían el aseo cuando lo solicitábamos, agua caliente, el staff muy amables y atentos. Solo el wifi a veces era lento más en la noches supongo porque ya todos llegábamos a esa hora :)

Reviewed on Mar 10, 2026

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 ￥15,021 per night from Mar 16 to Mar 17
￥15,021
￥16,824 total
Mar 16 - Mar 17
includes taxes & fees
7.6/10 Good! (1,005 reviews)
Wish there was a way to show when the pool is closed. We had a choice of similar hotels - selected this one based on location and our family likes to enjoy having access to a pool during a vacation. The hotel needs quite a bit of TLC - our room cleanliness was okay but there as a bad looking white ...

Reviewed on Mar 8, 2026

Best Western Plus Kingston Hotel And Conference Center
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Fully refundableReserve now, pay when you stay
The price is ￥21,335 per night from Apr 9 to Apr 10
￥21,335
￥30,085 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (462 reviews)
Loved the experience

Reviewed on Mar 9, 2026

AutoCamp Catskills
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
The price is ￥16,897 per night from Mar 25 to Mar 26
￥16,897
￥21,659 total
Mar 25 - Mar 26
includes taxes & fees
9.2/10 Wonderful! (880 reviews)
So close to Hunter Mountain, we made first chairs everyday! Very clean, great restaurant, perfect location! King Room with Patio was very large and comfortable. Great pillows too!

Reviewed on Mar 9, 2026

Hunter Lodge, a Bluebird by Lark
See all 2,162 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 ￥295,022, 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.