Annandale-on-Hudson Vacations from $2,067

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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.
  • Dec 18 - Dec 22

    The Hollow by Avantstay Shared Firepit + Deck Near Hunter Mountain + Hiking + Waterfalls + Flight

    Tannersville
    4 nights
    3.0 star property
    Roundtrip • St. George's Parish (BDA) - Poughkeepsie (POU)
    BDA - EWR • Nonstop EWR - BDA • Nonstop
    $2,483
    $2,067
    per traveler
    found 1 day ago
    The Hollow by Avantstay Shared Firepit + Deck Near Hunter Mountain + Hiking + Waterfalls
  • Dec 18 - Dec 22

    Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay + Flight

    Tannersville
    4 nights
    3.0 star property
    Roundtrip • St. George's Parish (BDA) - Poughkeepsie (POU)
    BDA - EWR • Nonstop EWR - BDA • Nonstop
    Save 100% on your flight
    $4,755
    $3,864
    per traveler
    found 1 day ago
    Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay
  • Dec 18 - Dec 22

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

    Hensonville
    4 nights
    3.0 star property
    Roundtrip • St. George's Parish (BDA) - Hudson (HCC)
    BDA - EWR • Nonstop EWR - BDA • Nonstop
    Save 100% on your flight
    $3,826
    $3,122
    per traveler
    found 1 day ago
    Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
  • Dec 18 - Dec 22

    The Summit by Avantstay Hot Tub + Playroom + Firepit Near Hunter Mountain Skiing + Hiking + Flight

    Tannersville
    4 nights
    3.0 star property
    Roundtrip • St. George's Parish (BDA) - Poughkeepsie (POU)
    BDA - EWR • Nonstop EWR - BDA • Nonstop
    $2,728
    $2,240
    per traveler
    found 1 day ago
    The Summit by Avantstay Hot Tub + Playroom + Firepit Near Hunter Mountain Skiing + Hiking
  • Dec 18 - Dec 22

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

    Hensonville
    4 nights
    3.0 star property
    Roundtrip • St. George's Parish (BDA) - Hudson (HCC)
    BDA - EWR • Nonstop EWR - BDA • Nonstop
    Save 100% on your flight
    $4,003
    $3,302
    per traveler
    found 1 day ago
    Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Where to stay near Annandale-on-Hudson

Discover the charm of Annandale-on-Hudson, nestled in the picturesque Hudson Valley. Explore nearby Hudson, NY, known for its vibrant arts scene and outdoor adventures. Visit wildflower farms during high season for breathtaking views and family-friendly activities, making your getaway both cultural and relaxing.

Catskill

For outdoor enthusiasts and culture seekers wanting a memorable trip, Catskill offers a captivating blend of nature and history. Nestled about 20 miles by car from Annandale-on-Hudson, this charming city invites visitors to explore the stunning Kaaterskill Falls, the historic Olana State Historic Site, and the serene Dutchman’s Landing urban park. With seasonal peaks in July and from December to January, Catskill is an ideal choice for a weekend getaway or an adventurous retreat, making it a smart hotel booking option.

Kingston

Experience the charm of Kingston, an excellent hub for families, adventure seekers, and couples who want to explore the rich outdoor activities in the area. With attractions like the historic Bard College, the scenic Esopus Creek, and the lively Dutchess County Fairgrounds, Kingston offers a delightful mix of culture and adventure year-round. Located about 11 miles by car from Annandale-on-Hudson, it makes for an easy getaway that caters to a variety of interests, ensuring a memorable stay.

Woodstock

If you are an art enthusiast or a nature lover, look no further than Woodstock, which features stunning scenery, vibrant arts, and outdoor adventures. Known for its beautiful mountains and waterfalls like Kaaterskill Falls, Woodstock is a perfect base for exploring Bethel Woods Museum and Bard College. Located about 20 miles by car from Annandale-on-Hudson, this charming city offers a year-round getaway with something for everyone, making it a smart choice for your stay.

Rhinebeck

Rhinebeck stands out as a prime spot for travelers interested in culture and outdoor adventures. With its charming atmosphere, visitors can easily access attractions like the Omega Institute, Dutchess County Fairgrounds, and Bard College, each offering unique experiences throughout the year. Located about 8 miles by car from Annandale-on-Hudson, Rhinebeck serves as a perfect base for exploring the scenic beauty and vibrant events of the Hudson Valley, making it a great choice for your stay.

Saugerties

Travelers seeking a vibrant cultural and outdoor experience will find Saugerties to be the ideal base for their vacation. This charming city offers access to attractions like Bard College, the HITS-on-the-Hudson equestrian center, and the Bethel Woods Museum, ensuring a rich blend of art, history, and adventure. Situated about 15 miles away from Annandale-on-Hudson, Saugerties is an excellent choice for those looking to explore the beauty of the Hudson Valley while enjoying a variety of seasonal activities.

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

Annandale-on-Hudson Hotel Deals

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.

Frequently Asked Questions

Is Annandale-on-Hudson better suited for a beach vacation or a cultural trip?

Annandale-on-Hudson is primarily a cultural destination, offering a rich history and academic atmosphere. A vacation here centers around sites like the Thomas Cole National Historic Site, about 8 miles from the city center, and the historic Blithewood mansion on the Bard College campus, which houses the Levy Economics Institute.


The area also features attractions such as the Dutchess County Fairgrounds, about 3 miles away, and Clinton Vineyards, located about 15 miles from the center, providing a blend of events and leisure. The region offers ample outdoor activities at places like Sleepy Hollow Lake and Kaaterskill Falls for those seeking nature. An Annandale-on-Hudson vacation package allows you to explore these diverse cultural and natural offerings.

How can I save money on a Annandale-on-Hudson vacation package?

When you bundle, you can save up to 30%*. To save money on a Annandale-on-Hudson package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Annandale-on-Hudson?

An Annandale-on-Hudson vacation offers a mix of cultural experiences and natural beauty:


Browse and book things to do in Annandale-on-Hudson on Expedia.

Can I change or cancel my Annandale-on-Hudson vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Annandale-on-Hudson vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Annandale-on-Hudson vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Annandale-on-Hudson vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Annandale-on-Hudson?

To find last-minute vacation packages to Annandale-on-Hudson, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Annandale-on-Hudson vacation packages?

Free cancellation on a Annandale-on-Hudson vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Annandale-on-Hudson vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Annandale-on-Hudson getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Annandale-on-Hudson vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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