Town of Olive Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Town of Olive Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was CA $1,801, price is now CA $1,159 per person
CA $1,159
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,941 reviews)
Fun place to stay with a tropical vibe on a gray winter day. Very convenient to Times Square and the surrounding areas. Loved the different bars, Margaritaville, Land Shark and the Roof Top. Would definitely stay again.

Reviewed on Mar 3, 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Manhattan
Price was CA $2,235, price is now CA $1,311 per person
CA $1,311
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (31 reviews)
Cool room with a comfortable bed and a full kitchen very sweet staff. It’s close to the New York Public library, MOMA, Times Square, and more.

Reviewed on Mar 2, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $2,765, price is now CA $1,725 per person
CA $1,725
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,000 reviews)
Spotless property and extremely friendly staff! Would definitely stay here again!

Reviewed on Mar 1, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,698, price is now CA $2,315 per person
CA $2,315
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (189 reviews)
Absolutely everything. Amazingly appointed room, very friendly stafff.

Reviewed on Mar 1, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,576, price is now CA $1,643 per person
CA $1,643
per person
May 29 - May 31
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
Very amazing place, everything is picture worthy.

Reviewed on Feb 21, 2026

The Annual Vacation Sale

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Town of Olive Hotel Deals

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Mar 15 to Mar 16
CA $161
CA $181 total
Mar 15 - Mar 16
includes taxes & fees
9/10 Wonderful! (864 reviews)
Room is clean. Staff was friendly. Check-in was fast. Parking was free and there was adequate space.

Reviewed on Mar 2, 2026

Residence Inn by Marriott Kingston
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Mar 22 to Mar 23
CA $206
CA $284 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (459 reviews)
The staff and eme

Reviewed on Feb 28, 2026

AutoCamp Catskills
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
The price is CA $159 per night from Mar 22 to Mar 23
CA $159
CA $201 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (876 reviews)
The hotel was crawling with inconsiderate families with extremely loud children

Reviewed on Mar 1, 2026

Hunter Lodge, a Bluebird by Lark
See all 2,170 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 $1,159, 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.