Town of Olive Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Town of Olive Vacation Deals

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

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,648, price is now CA $971 per person
CA $971
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (2,492 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,191, price is now CA $3,693 per person
CA $3,693
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,007 reviews)

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,719, price is now CA $1,090 per person
CA $1,090
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (7,641 reviews)
There was dust on the headboard, the sheets were wrinkled, and I found hair on the pillow. However, it is quiet and the staff is friendly. It could be more appealing if they made changes—like adding a coffee maker or small fridge to the room and making better use of the bar. It could be a very attractive hotel given its historic character, but it needs a little more TLC.

Reviewed on Aug 3, 2026

East Norwich Inn

East Norwich Inn

2.5 out of 5
Price was CA $1,563, price is now CA $1,002 per person
CA $1,002
per person
Oct 11 - Oct 17
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,842 reviews)
It serves its purpose. But the room decor is very outdated. And no elevators. In my mini fridge I found someone’s old food that they left in there. But it was clean and quiet.

Reviewed on Aug 3, 2026

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was CA $1,901, price is now CA $1,225 per person
CA $1,225
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,498 reviews)
Staff was absolutely amazing. So warm, friendly, and helpful. Room was very nice, clean, comfortable. Wouldn’t hesitate to stay there again.

Reviewed on Aug 2, 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 CA $212 per night from Aug 5 to Aug 6
CA $212
CA $240 total
Aug 5 - Aug 6
includes taxes & fees
Beekman Arms and Delamater Inn
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 CA $170 per night from Sep 2 to Sep 3
CA $170
CA $214 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"When you reach a certain age, it is very helpful to have more light. Hallway lighting was dim Could use more light in the room. Bathroom had adequate lighting. We came in July- wow, room would probably have been much darker in winter"

Reviewed on Aug 3, 2026

Hunter Lodge, a Bluebird by Lark
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 CA $125 per night from Sep 2 to Sep 3
CA $125
CA $140 total
Sep 2 - Sep 3
includes taxes & fees
SureStay Plus Hotel by Best Western Highland Poughkeepsie
See all 2,229 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.
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Frequently asked questions

How much does a Town of Olive vacation package cost?
Starting from only CA $971, 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.