Town of Olive Vacations & Trips from ￥308,798

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Sep 13 - Sep 21
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
7.6/10 Good! (796 reviews)
The stag was pleasant , the room was in clean condition , the price was great and we would recommend and stay there again .

Reviewed on Jun 25, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 13 - Sep 21
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,385 reviews)
Great centrally located modern hotel with all convenience you expect from top class hotel!

Reviewed on Jun 28, 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
per person
Sep 13 - Sep 21
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (2,725 reviews)
Nice and modern hotel, small rooms which make sense for NYC, and great hotel staff. Confusing emails, the parking email had the wrong hotel location, but otherwise it was a good stay.

Reviewed on Jun 27, 2025

The Dominick

The Dominick

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 13 - Sep 21
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The Dominick was an excellent choice in a great part of NYC. Nice rooms with and a helpful and pleasant front desk staff. The only downside was the small lobby.

Reviewed on Jun 27, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 13 - Sep 21
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (1,212 reviews)
Lovely small quiet hotel, great staff and rooms- not huge which is typical of New York but would definitely stay again

Reviewed on Jun 28, 2025

Town of Olive Hotel Deals

Beekman Arms Hotel
Beekman Arms Hotel
3.5 out of 5
6387 MILL ST, Rhinebeck, NY
8.2/10 Very Good! (720 reviews)
"Nice old inn and good breakfast"

Reviewed on Jun 19, 2025

Get rates
Beekman Arms Hotel
Quality Inn Hyde Park Poughkeepsie North
Quality Inn Hyde Park Poughkeepsie North
2.5 out of 5
4142 Albany Post Rd, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is ￥12,888 per night from Jul 6 to Jul 7
￥12,888
￥14,580 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (1,010 reviews)
"Clean and quiet hotel. Very friendly and helpful staff"

Reviewed on Jun 23, 2025

Quality Inn Hyde Park Poughkeepsie North
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is ￥23,289 per night from Jul 20 to Jul 21
￥23,289
￥26,347 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (342 reviews)
"This place is amazing shower was excellent will be booking another stay in September 👍👍👍👍👍"

Reviewed on Jun 26, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 2,112 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 ￥308,798, 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.