Red Hook Vacations from $667

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Your Red Hook Vacation

When a break in the city is calling, answer it with a vacation package to Red Hook. The neighborhood of Kingston Stockade District, which is good for families, festivals and markets, makes a great base for your adventures. Fill your free time with tours of Bard College, Dutchess County Fairgrounds and Old Rhinebeck Aerodrome, some of the things you just have to see during your trip to Red Hook. A couple of quick clicks is all it takes to put together the ideal Red Hook vacation on Expedia.

The Latest Red Hook vacation packages

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

The Perch Hotel

2 out of 5
Price was $865, price is now $667 per person
$667
per person
Jul 31 - Aug 3
found 5 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.6/10 Exceptional! (31 reviews)
Check in information was provided via email the day of check in. I was able to enter the hotel and my room without a problem. The hotel staff was responsive and helpful via text messages. The inside of our room was very comfortable, the staff left a few complementary drinks and snack in the room for us which was very much appreciated. The room had a home feeling to it which made for a comfortable stay. The location was safe, quiet and had lovely mountain side views. This location was close to many popular hiking spots in the area we had a lot of fun.

Reviewed on Jun 3, 2026

Amaya Bed&Breakfast

Amaya Bed&Breakfast

2 out of 5
Save 100% on your flight
Price was $1,119, price is now $832 per person
$832
per person
Jul 31 - Aug 3
found 5 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
10/10 Exceptional! (18 reviews)
Johnny was such a fantastic host. Not only were accomodations beautiful with a great breakfast but also his recommendations and quick response to emails made for a great weekend getaway. Hot tub is amazing.

Reviewed on May 23, 2026

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $958, price is now $771 per person
$771
per person
Jul 31 - Aug 3
found 5 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9/10 Wonderful! (369 reviews)
Place was nice looking but the amenity fee is crazy high and the continental breakfast is lacking a lot!

Reviewed on May 31, 2026

Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
Price was $990, price is now $822 per person
$822
per person
Jul 31 - Aug 3
found 5 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (241 reviews)
Everything was wonderful! Perfect for a long weekend getaway

Reviewed on May 7, 2026

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $961, price is now $830 per person
$830
per person
Jul 31 - Aug 3
found 5 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.6/10 Excellent! (46 reviews)
Very nice property right in downtown Hudson. Rooms are small but cute and with all amenities.

Reviewed on Jun 21, 2026

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Stay near popular Red Hook attractions

A biplane with red and white stripes flying against a clear blue sky.

Old Rhinebeck Aerodrome

9.4/5 (8 reviews)
This living aviation museum displays rare flyable aircraft (1900-1935) with weekend airshows featuring WWI dogfights. Experience the golden age of flight with an open-cockpit biplane ride over the Hudson Valley.
See properties

Red Hook Hotel Deals

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Jul 1 to Jul 2
$94 total
Jul 1 - Jul 2
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"Overall, very happy with our stay, will be back. There was a problem with our first room, but the staff and manager fixed the issue and provided another acceptable room. All of the staff that we dealt with were very helpful and accommodating, pleasant to deal with. If you travel a lot, you know that ..."

Reviewed on Jun 26, 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $121 total per night from Jul 5 to Jul 6
$121 total
Jul 5 - Jul 6
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
"I roasted I was told the AC system was getting worked on and would be back shortly I spent the entire night roasting the temp didn’t go below 84 the entire time there."

Reviewed on Jun 25, 2026

DoubleTree by Hilton Poughkeepsie Convention Center
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$202 nightly
The price is $226 total per night from Jul 9 to Jul 10
$226 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (519 reviews)
"Pet friendly was ideal. The only thing I would say negatively is that the Airstream could have used wipe down with some Clorox wipes, ect. & maybe a few more hooks here and there given the tight quarters :) Overall though ... 8.5 outta 10. Will recommend to others! Thanks Autocamp!"

Reviewed on Jun 26, 2026

AutoCamp Catskills
See all 2,018 properties in Red Hook
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 Red Hook Vacation Packages

Red Hook Essential Information

Language
English
Currency
U.S dollars
Population
2,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
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 a Red Hook vacation package cost?
You can snap up a vacation package to this destination from $667 on Expedia. But how much your vacation to Red Hook costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Red Hook?
December, January and February are great times to search for cheap Red Hook vacation packages. Traveling in less busy months means you can generally find lower prices on accommodations and flights.
How many days is enough for Red Hook?
The ideal duration of your Red Hook vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to go to all the top sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Red Hook?
Red Hook has all the ingredients you need for an awesome getaway — walking trails, history and golfing are just the start. Whether you'd like to check out sights like Old Rhinebeck Aerodrome and Red Hook Golf Club, or take the road less traveled, there's plenty to explore on your Red Hook vacation.
How to find the best Red Hook package deals?
Start your search for a Red Hook package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Red Hook package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Red Hook getaway off to a flying start.
Is it cheaper to book a Red Hook vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight 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 enjoy the flexibility to create a tailored Red Hook vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Red Hook?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Red Hook escape.
Does Expedia offer Book Now, Pay Later Red Hook vacation packages?
Set off on your dream escape to Red Hook with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.