Annandale-on-Hudson Vacations

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Your Annandale-on-Hudson Vacation

The easiest way to experience this lively city is with a customized Annandale-on-Hudson vacation package. Base yourself in the neighborhood of Kingston Stockade District, which is good for families, festivals and markets or go someplace else — our packages are all about you. If a sightseeing tour is on the to-do list during your trip to Annandale-on-Hudson, swing by big attractions like Bard College, Dutchess County Fairgrounds and Old Rhinebeck Aerodrome. Stop daydreaming and start doing. Check out the multitude of options on Expedia today and put your Annandale-on-Hudson vacation plans into gear!

Discover the most popular places to visit in Annandale-on-Hudson

Bard College

4.5/5(61 reviews)

Enjoy the collegiate vibe at Bard College during your visit to Annandale-on-Hudson. Stroll along the marina or experience the area's festivals.

Bard College

Hessel Museum of Art

You can study the exhibits at Hessel Museum of Art, a museum with a story of its own, during your travels to Annandale-on-Hudson. Stroll along the marina or experience the area's festivals.

Hessel Museum of Art

Annandale-on-Hudson Hotel Deals

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
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $147 total per night from Sep 7 to Sep 8
$147 total
Sep 7 - Sep 8
Total with taxes and fees
Best Western Plus Kingston Hotel And Conference Center
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

2.5 out of 5
4142 Albany Post Rd, Hyde Park, NY
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Sep 7 to Sep 8
$91 total
Sep 7 - Sep 8
Total with taxes and fees
Quality Inn Hyde Park Poughkeepsie North
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
$163 nightly
The price is $176 total per night from Sep 7 to Sep 8
$176 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (743 reviews)
"Comfortable, clean room. Beautiful surroundings. Friendly, helpful staff."

Reviewed on Aug 23, 2025

Hunter Lodge, a Bluebird by Lark
See all 1,683 properties in Annandale-on-Hudson
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 an Annandale-on-Hudson vacation package cost?
You can snap up a vacation package to this destination on Expedia. But how much your vacation to Annandale-on-Hudson costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Annandale-on-Hudson?
If you're hoping to snag a cheap Annandale-on-Hudson vacation package, consider planning a trip in December, January and February. You'll typically find lower rates on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Annandale-on-Hudson?
The ideal duration for your Annandale-on-Hudson vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to hit all the leading attractions and explore some hidden treasures along the way.
Is it worth booking a vacation package to Annandale-on-Hudson?
Annandale-on-Hudson is a good vacation destination with attractions like Montgomery Place among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, an Annandale-on-Hudson vacation promises fun for everyone.
How to find the best Annandale-on-Hudson package deals?
Begin your search for an Annandale-on-Hudson package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," 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 Annandale-on-Hudson package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Annandale-on-Hudson adventure underway.
Is it cheaper to book an Annandale-on-Hudson vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a personalized Annandale-on-Hudson vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Annandale-on-Hudson?
If you've got your Annandale-on-Hudson travel dates finalized, book early to bag some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Annandale-on-Hudson vacation packages?
Your Annandale-on-Hudson getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.