Red Hook Vacations from $381

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $492, price is now $381 per person
$381
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
8.8/10 Excellent! (2,369 reviews)
Beautiful property in the middle of the mountains

Reviewed on May 28, 2026

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $1,058, price is now $750 per person
$750
per person
Jul 23 - Jul 26
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.6/10 Exceptional! (30 reviews)
This is a really charming hotel with amazing views and very friendly and helpful staff. We wish we could've stayed longer!

Reviewed on May 26, 2026

The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $596, price is now $461 per person
$461
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,010 reviews)
Beautiful and well maintained and close to shipping and food

Reviewed on May 29, 2026

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $502, price is now $392 per person
$392
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9/10 Wonderful! (949 reviews)
The room was clean and comfortable, the staff was friendly and helpful..only negative is that the furniture in the room is in serious need of replacement… veneers on end tables lifting, upholstered kitchen chairs all had rips…

Reviewed on May 27, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $508, price is now $410 per person
$410
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (902 reviews)
The rooms are not at all fancy, but perfect for a family if you want to get away for a few nights. We went with my 3, 4, and 7-year-olds and spent two nights playing in the pool, mini-golfing, and hitting the arcade once or twice. Again, not very high-end, but if you’re with children who love a pool and easy activities, it’s a good choice.

Reviewed on May 25, 2026

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Discover the most popular places to visit in Red Hook

Fokker DR1 Triplane at Old Rhinebeck Aerodrome Rhinebeck NY.

Old Rhinebeck Aerodrome

5/5(2 reviews)

You can browse the exhibits at Old Rhinebeck Aerodrome, a museum with a story of its own, during your travels to Red Hook. Stroll along the marina or experience the area's festivals.

Old Rhinebeck Aerodrome

Red Hook 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
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
"There was a hole in my door so anyone could look in. Pool always closed."

Reviewed on May 30, 2026

Best Western Plus Kingston Hotel And Conference Center
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$209 nightly
The price is $226 total per night from Jun 30 to Jul 1
$226 total
Jun 30 - Jul 1
Total with taxes and fees
9.6/10 Exceptional! (237 reviews)
"Very relaxing,"

Reviewed on May 30, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$189 nightly
The price is $212 total per night from Jun 24 to Jun 25
$212 total
Jun 24 - Jun 25
Total with taxes and fees
9/10 Wonderful! (509 reviews)
"Took a trip for a night with a couple of friends and we all really loved our stay! Comfortable bed, great amenities, the place was clean. Great kitchen supplies for cooking food over the fire. Would 10/10 return!"

Reviewed on May 28, 2026

AutoCamp Catskills
See all 1,991 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 $381 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.