Town of Olive Vacations & Trips from ￥402,053

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The Latest Town of Olive Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥669,025, price is now ￥402,053 per person
￥402,053
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.6/10 Exceptional! (714 reviews)
Very nice and updated hotel; like the location - would def stay again

Reviewed on Jul 24, 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Price was ￥1,540,114, price is now ￥868,712 per person
￥868,712
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was ￥949,980, price is now ￥559,905 per person
￥559,905
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Large 2 Bedrooms with Queen Beds

Large 2 Bedrooms with Queen Beds

4 out of 5
Manhattan
Price was ￥1,442,681, price is now ￥860,733 per person
￥860,733
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
No reviews

Aloft by Marriott New York Brooklyn

Aloft by Marriott New York Brooklyn

3 out of 5
Price was ￥1,368,452, price is now ￥822,009 per person
￥822,009
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (1,168 reviews)
Our room was very clean and the staff was great. My daughter and I had a lovely stay. Thank you!

Reviewed on Jul 24, 2026

Town of Olive Hotel Deals

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
The price is ￥24,747 per night from Jul 28 to Jul 29
￥24,747
￥27,994 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very Good! (934 reviews)
"Poorly maintained. Broken window that could not be shut,broken curtain track, broken drawer in bathroom, leaking faucet in bathroom, etc,etc. The free continental breakfast was abysmal. The room we had was at best a 200$ value and even that is probably a stretch. Won't be coming back."

Reviewed on Jul 25, 2026

Beekman Arms and Delamater Inn
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 ￥17,201 per night from Aug 16 to Aug 17
￥17,201
￥19,265 total
Aug 16 - Aug 17
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"The bed with its big puffy pillows was incredibly comfortable. Great sleep. Staff was friendly and very kind. Great place to spend a night or three"

Reviewed on Jul 25, 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
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 ￥23,264 per night from Aug 10 to Aug 11
￥23,264
￥28,664 total
Aug 10 - Aug 11
includes taxes & fees
Hunter Lodge, a Bluebird by Lark
See all 2,213 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 ￥402,053, 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.

Stay near popular Town of Olive attractions

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.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.