Olivebridge Vacations from $621
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The Latest Olivebridge vacation packages
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
$1,150
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
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View all tripsStay 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.
Olivebridge Hotel Deals
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Olivebridge NY
10/10 Exceptional! (62 reviews)
"Had a great time staying here. Quiet, comfortable and conveniently located. Didn’t get to meet the hosts but they left clear and helpful instructions for checking in and exploring the area. First time in the area and was pleasantly surprised by the many options for restaurants and hiking. Already ..."
Reviewed on Aug 10, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$129 nightly
$146 total
Aug 16 - Aug 17
Total with taxes and fees
8.2/10 Very Good! (968 reviews)
"We’ve stayed here a few times as we are parents of a college student in the area. Price is reasonable and it is always clean and easy to navigate. Highly recommend."
Reviewed on Aug 12, 2026
Hunter Lodge, a Bluebird by Lark
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$138 nightly
$149 total
Sep 1 - Sep 2
Total with taxes and fees
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.
Find the Best Olivebridge Vacation Packages
Olivebridge Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Top Sights | Ulster Performing Arts Center, Mount Tremper Arts and James Cox Gallery |
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Frequently asked questions
How much does an Olivebridge vacation package cost?
Offering excellent value package deals from $621 on Expedia, you'll be surprised at how little a vacation to Olivebridge costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Olivebridge?
November, December and January are great times to look for cheap Olivebridge vacation packages. Traveling in quieter months means you can typically find better prices on flights and hotels.
How many days is enough for Olivebridge?
With a well-organized travel plan, you can easily tick off the main Olivebridge sights in a handful of days. But if you prefer to venture off the beaten track or go on day tours, think about booking your Olivebridge vacation for longer.
How to find the best Olivebridge package deals?
Begin your search for an Olivebridge package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Olivebridge package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Olivebridge adventure underway.
Is it cheaper to book an Olivebridge vacation as a package?
You can enjoy significant savings on your Olivebridge retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Olivebridge?
If you're considering a spur-of-the-moment Olivebridge adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Olivebridge vacation packages?
Your Olivebridge getaway is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
