Town of Olive Vacation Packages

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    Save up to CA $1,096 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.
The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Manhattan
Price was CA $1,590, price is now CA $975 per person
CA $975
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was CA $2,614, price is now CA $1,540 per person
CA $1,540
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (625 reviews)
Everything was perfect from top to bottom.

Reviewed on Mar 5, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,098, price is now CA $1,863 per person
CA $1,863
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 $2,850, price is now CA $1,718 per person
CA $1,718
per person
May 15 - May 17
found 1 day 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

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was CA $2,850, price is now CA $1,840 per person
CA $1,840
per person
May 8 - May 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (1,350 reviews)
Lovely hotel, incredibly convenient location, significantly roomier than your typical New York hotel. I was especially impressed with the friendliness of the staff and the immaculate cleanliness of the hotel throughout. Some of the decor is vintage but in a way that makes it feel cool and custom.

Reviewed on Mar 5, 2026

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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 $160 per night from Mar 15 to Mar 16
CA $160
CA $179 total
Mar 15 - Mar 16
includes taxes & fees
9/10 Wonderful! (866 reviews)
The young Lady that was working the front desk on the morning of Monday and Tuesday March 2nd and 3rd, needs some training in customer service. I asked her a simple question about switching out the towels in my room because I was there for a few days, she was very rude and disrespectful. The next ...

Reviewed on Mar 6, 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 $195 per night from Apr 5 to Apr 6
CA $195
CA $272 total
Apr 5 - Apr 6
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
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Mar 31 to Apr 1
CA $153
CA $195 total
Mar 31 - Apr 1
includes taxes & fees
9.2/10 Wonderful! (878 reviews)
Beautiful property with great beds super close to the mountain and Tannersville. Great fire at breakfast. Our only wish is that they had more guests so that that the Tavern would be open for food and drinks on earlier days/nights in the week too. But we understand why it isn't. Also, the complimentary ...

Reviewed on Mar 4, 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 $975, 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.