Red Hook Vacations from $629

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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.
Studio 6 Lake George, NY - Adirondacks

Studio 6 Lake George, NY - Adirondacks

2 out of 5
Price was $906, price is now $629 per person
$629
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
9.2/10 Wonderful! (5 reviews)
The owners are super friendly, the rooms we surprisingly wonderful. Indoor and outdoor pool, loved the picnic table and grill out our back sliding doors!

Reviewed on Jul 29, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $2,110, price is now $1,242 per person
$1,242
per person
Oct 1 - Oct 8
found 5 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.6/10 Exceptional! (33 reviews)
It was a wonderful stay the room was very clean and spacious. The common area downstairs was my favorite part of my whole stay. Wide variety of games to play with other guest that are also staying.

Reviewed on Jul 16, 2026

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $2,472, price is now $1,525 per person
$1,525
per person
Oct 1 - Oct 8
found 5 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.8/10 Exceptional! (36 reviews)

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $2,341, price is now $1,489 per person
$1,489
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
9.4/10 Exceptional! (620 reviews)
Loved the room and the view was absolutely amazing. Not far from everything we wanted to do. Staff were nice and friendly.

Reviewed on Jul 29, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,013, price is now $677 per person
$677
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,000 reviews)

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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

9.4/10 (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

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
$139 nightly
The price is $157 total per night from Aug 2 to Aug 3
$157 total
Aug 2 - Aug 3
Total with taxes and fees
8.2/10 Very Good! (941 reviews)
"This is a lovely inn. I have always wanted to stay here. The bar was great. The food was amazing. However, the wifi did not function in my room. The check in staff did not inform me that coffee would be available in the lobby in the morning. Frankly, I found him somewhat condescending. The property ..."

Reviewed on Jul 29, 2026

Beekman Arms and Delamater Inn
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
$111 nightly
The price is $130 total per night from Aug 16 to Aug 17
$130 total
Aug 16 - Aug 17
Total with taxes and fees
DoubleTree by Hilton Poughkeepsie Convention Center
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
$89 nightly
The price is $100 total per night from Aug 16 to Aug 17
$100 total
Aug 16 - Aug 17
Total with taxes and fees
8/10 Very Good! (1,020 reviews)
"They were SUPER dog friendly which was great to see and we could walk around the property to give our pup some exercise and others were doing the same. It was very clean and very comfortable and everything we needed and looking for."

Reviewed on Jul 28, 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
See all 2,027 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 $629 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.