Annandale-on-Hudson Vacations from $1,150

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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

Wylder Hotel Windham

3.5 out of 5
Price was $1,332, price is now $1,150 per person
$1,150
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8.8/10 Excellent! (103 reviews)

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

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

3 out of 5
Save 100% on your flight
Price was $7,515, price is now $5,766 per person
$5,766
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews

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

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

3 out of 5
Save 100% on your flight
Price was $7,527, price is now $5,779 per person
$5,779
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
No reviews

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,463, price is now $1,324 per person
$1,324
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8/10 Very Good! (32 reviews)
Abia mucho ruido en la noche I abian muchas moscas y solo abia 1 cobija y eramos tres

Reviewed on Jul 25, 2026

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 $3,965, price is now $3,700 per person
$3,700
per person
Oct 9 - Oct 12
found 5 hours ago
Roundtrip flight included
New York (NYC) 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.
See properties

Annandale-on-Hudson Hotel Deals

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
$159 nightly
The price is $180 total per night from Jul 27 to Jul 28
$180 total
Jul 27 - Jul 28
Total with taxes and fees
8.2/10 Very Good! (937 reviews)
"I liked the property. Thought there could be more lights outside by dinner tables. Got to do something about the skunks that are near main lodge area patio rooms. Otherwise was a great experience hotel. Like how they had kitchen area and living room area in the one lodge area but rooms were small. ..."

Reviewed on Jul 26, 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
$141 nightly
The price is $152 total per night from Aug 10 to Aug 11
$152 total
Aug 10 - Aug 11
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
$209 nightly
The price is $226 total per night from Aug 25 to Aug 26
$226 total
Aug 25 - Aug 26
Total with taxes and fees
9.6/10 Exceptional! (261 reviews)
"It was great!"

Reviewed on Jul 26, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 1,740 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 $1,150 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.