Olivebridge 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 Olivebridge Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Echo Valley Cottages

Echo Valley Cottages

3 out of 5
Price was CA $1,761, price is now CA $1,064 per person
CA $1,064
per person
Aug 10 - Aug 17
just found
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.6/10 Excellent! (62 reviews)
The place was very clean and the manager was excellent. Definitely would go back.

Reviewed on Jun 25, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,781, price is now CA $9,288 per person
CA $9,288
per person
Aug 16 - Aug 22
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,957, price is now CA $1,872 per person
CA $1,872
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,652 reviews)
The proximity to all the things we love was great. Elevators were fast! Staff very helpful and pleasant. Enjoyed the coffee shop and lounge at 7:00 while the rest of my crew slept. Would stay there again. Only concern…low water pressure in shower.

Reviewed on Jul 4, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,331, price is now CA $2,764 per person
CA $2,764
per person
Sep 10 - Sep 13
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Atmosphere was amazing. Layout was incredibly unique. Will definitely be returning

Reviewed on Jul 2, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,487, price is now CA $1,593 per person
CA $1,593
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,130 reviews)
The breakfast bar was very clean and the variety of good was great!

Reviewed on Jul 4, 2026

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Olivebridge Hotel Deals

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Olivebridge NY
10/10 Exceptional! (60 reviews)
"It was beautiful and cozy, just as described. The hosts were very communicative and helpful, and the place was exceptionally clean. I honestly didn’t want to leave! We had a wonderful stay and will definitely be making plans to return in the future."

Reviewed on Jun 24, 2026

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Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
7.4/10 Good! (1,001 reviews)
"Room was clean."

Reviewed on Jul 2, 2026

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Best Western Plus Kingston Hotel And Conference Center
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from Jul 20 to Jul 21
CA $288
CA $379 total
Jul 20 - Jul 21
includes taxes & fees
AutoCamp Catskills
See all 1,954 properties in Olivebridge
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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Stay near popular Olivebridge attractions

Brown's Station

Explore the great outdoors at Brown's Station, a lovely green space in Olivebridge. Amble around the area's forest or experience its entertainment venues.
See properties

Frequently asked questions

How much does an Olivebridge vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,064 on Expedia. But how much your vacation to Olivebridge costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Olivebridge?
If you'd like to book a cheap Olivebridge vacation package, consider planning a trip in January, February and March. You'll typically find better prices on flights and accommodations during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Olivebridge?
The ideal length of your Olivebridge vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you plenty of time to check out all the top sights and discover some hidden gems along the way.
How to find the best Olivebridge package deals?
Finding a cheap Olivebridge package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Olivebridge package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Olivebridge vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Olivebridge trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Olivebridge?
If you've got your Olivebridge travel dates locked in, book as soon as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Olivebridge?

  1. Choose when to go: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Olivebridge.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and experiences. Your hotel will probably be the biggest expense during your trip to Olivebridge.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Olivebridge. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the right Olivebridge vacation package for you.

Explore a world of travel with Expedia

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