Olivebridge Vacations from $486

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The Latest Olivebridge vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $877, price is now $486 per person
$486
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,728, price is now $924 per person
$924
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!

Reviewed on Oct 19, 2026

33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,909, price is now $1,025 per person
$1,025
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,003 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,017, price is now $551 per person
$551
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was $990, price is now $540 per person
$540
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,314 reviews)

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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

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! (64 reviews)
"Clean, cozy, everything I needed for my stay. Loved having the air purifier since I have environmental allergies when the leaves fall. It saved my sleep and allowed me to skip antihistamines! Thank you! The bed is super comfortable, great shower pressure and temp, well-equipped kitchen, and I loved ..."

Reviewed on Oct 18, 2026

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Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
$169 nightly
The price is $191 total per night from Nov 9 to Nov 10
$191 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Room was clean and very spacious! Loved the gas fireplace."

Reviewed on Oct 27, 2026

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
$138 nightly
The price is $149 total per night from Nov 8 to Nov 9
$149 total
Nov 8 - Nov 9
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
"👍"

Reviewed on Oct 27, 2026

Hunter Lodge, a Bluebird by Lark
See all 1,988 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.

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 $486 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.