Red Hook Vacations from $745

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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.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $1,055, price is now $745 per person
$745
per person
Jan 7 - Jan 14
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.4/10 Exceptional! (658 reviews)
My husband and I really enjoyed the stay at this hotel. We were stunned on how beautiful the property was, especially inside the hotel room. Everything was immaculate. We will absolutely be staying here again ❤️ we cannot wait to plan our next adventure here to the Lodges at Cresthaven ❤️

Reviewed on Nov 1, 2026

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

The Nightingale by Avantstay Historic Catskills Retreat Lake Views + Near Hudson Sleeps 18

3 out of 5
Save 100% on your flight
Price was $2,837, price is now $2,140 per person
$2,140
per person
Jan 8 - Jan 11
found 5 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
No reviews

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,472, price is now $1,132 per person
$1,132
per person
Dec 21 - Dec 26
found 10 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (22 reviews)
The place was clean and beautiful. You need to check with Expedia . I didn’t get the steps to get in, since there is nobody on site. to check in. I call the phone on site. Somebody call me back and walk me through step to get in.

Reviewed on Oct 19, 2026

Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $1,196, price is now $1,015 per person
$1,015
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (709 reviews)
There was no staff on-site, and all communication was handled through text messages. Other than that, it’s a nice and clean place. Just keep in mind that, there is no daily housekeeping, so be prepared to reuse your towels and bed sheets during your stay.

Reviewed on Nov 4, 2026

Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was $1,864, price is now $1,617 per person
$1,617
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (136 reviews)
Beautiful serene large property with many interesting art sculptures throughout. Close to downtown Manchester but need car. Very memorable.

Reviewed on Oct 24, 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

9.4/10 (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

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Fully refundable
$93 nightly
The price is $108 total per night from Nov 29 to Nov 30
$108 total
Nov 29 - Nov 30
Total with taxes and fees
Quality Inn Poughkeepsie
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
$119 nightly
The price is $134 total per night from Dec 8 to Dec 9
$134 total
Dec 8 - Dec 9
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"The sight says they have AC, we were given room 25, no AC We were under the impression it was a B&B. We had to leave the property and go to their property called Delmater for really bad pastry those Items hard boiled eggs peeled just sitting in a bowl and other exposed fruit etc. We could only open ..."

Reviewed on Nov 7, 2026

Beekman Arms and Delamater Inn
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

4.5 out of 5
549 Washington Street Hudson NY
Fully refundableReserve now, pay when you stay
$273 nightly
The price is $308 total per night from Dec 1 to Dec 2
$308 total
Dec 1 - Dec 2
Total with taxes and fees
8.6/10 Excellent! (103 reviews)
"not worth the price!"

Reviewed on Nov 2, 2026

Pocketbook Hotel and Bath
See all 2,017 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 $745 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.