Annandale-on-Hudson Vacations from $477

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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.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $540, price is now $477 per person
$477
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Hudson (HCC)
9.4/10 Exceptional! (818 reviews)
We always like staying here. The bed is super comfortable and the outdoor area is very pretty. The receptionist was very nice. Did not ask her name but she works Sunday evening and Monday morning.

Reviewed on Jul 18, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $594, price is now $520 per person
$520
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Hudson (HCC)
8/10 Very Good! (32 reviews)

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Price was $2,295, price is now $2,105 per person
$2,105
per person
Sep 12 - Sep 16
found 4 hours ago
Roundtrip non-stop flight included
Evansville (EVV) to Hudson (HCC)
No reviews

Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $634, price is now $595 per person
$595
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Hudson (HCC)
9.2/10 Wonderful! (107 reviews)
The place is perfect for couples, very quiet and relaxing. The cabin was clean and well mantained, the property has bikes that you can use. They welcome you with a smores kit. I recommend this place a lot!

Reviewed on Jul 13, 2026

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

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

3 out of 5
Price was $1,664, price is now $1,648 per person
$1,648
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Washington (DCA) to Hudson (HCC)
No 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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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
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Best Western Plus Kingston Hotel And Conference Center
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $175 total per night from Jul 21 to Jul 22
$175 total
Jul 21 - Jul 22
Total with taxes and fees
8.2/10 Very Good! (930 reviews)
"Wonderful old charming Inn, with newer beds and bathrooms, in the heart of Rhinebeck!"

Reviewed on Jul 19, 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
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $155 total per night from Aug 10 to Aug 11
$155 total
Aug 10 - Aug 11
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"The rooms were cool and the food at the Lodge Tavern by chef Kieran was amazing- best smash burger in the Catskills 100%"

Reviewed on Jul 18, 2026

Hunter Lodge, a Bluebird by Lark
See all 1,730 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 $477 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.