Annandale-on-Hudson Vacations from $866

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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!

The Latest Annandale-on-Hudson vacation packages

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

Wylder Hotel Windham

$866

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Grand Rapids (GRR) to Hudson (HCC)

8.8/10 Excellent! (120 reviews)

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Save 100% on your flight

$3,482

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Hudson (HCC)

No reviews

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Save 100% on your flight

$3,680

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Hudson (HCC)

No reviews

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Save 100% on your flight

$1,671

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Hudson (HCC)

No reviews

Eastwind Windham

$991

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Grand Rapids (GRR) to Hudson (HCC)

9.2/10 Wonderful! (116 reviews)

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Stay near popular Annandale-on-Hudson attractions

Bard College

8.6/10 (100 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.

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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.

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Annandale-on-Hudson Hotel Deals

Beekman Arms and Delamater Inn

6387 MILL ST Rhinebeck NY

$152 nightly

$172 total

Sep 23 - Sep 24

Total with taxes and fees

8.2/10 Very Good! (1,002 reviews)

"Cozy, comfy. Relaxing. Roomy. Even had a bookshelf loaded with paperbacks! Hand hardcover too!"

Reviewed on Sep 15, 2026

Hunter Lodge, a Bluebird by Lark

7433 Main St Hunter NY

$155 nightly

$168 total

Sep 29 - Sep 30

Total with taxes and fees

9.2/10 Wonderful! (1,008 reviews)

"Beautiful Mountain View’s in the Catskills. Just a mile or so to the quaint village of Tannersville. With restaurants and artisan gift shops. Driving through Kaaterskill Falls trail is worth the trip."

Reviewed on Sep 15, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

282 Cairo Junction Rd Catskill NY

$209 nightly

$226 total

Sep 17 - Sep 18

Total with taxes and fees

9.6/10 Exceptional! (297 reviews)

"Everything was so smooth, from the detailed map and heads up of possible cell service interruptions, to the check in and check out process, housekeeping request, and the ease of communication via text. It was a perfect getaway, minimal interruptions, yet easy to reach with quick responses. Although ..."

Reviewed on Sep 16, 2026

See all 1,733 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.

Find the Best Annandale-on-Hudson Vacation Packages

Annandale-on-Hudson Essential Information

Language	English
Currency	U.S dollars
Top Sights	Old Rhinebeck Aerodrome, Center for Performing Arts at Rhinebeck and Margaret Lewis Norrie State Park

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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 from $866 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.