Red Hook Vacations from $713

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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 $945, price is now $713 per person
$713
per person
Jul 14 - Jul 19
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
8.8/10 Excellent! (2,388 reviews)
Property is great and stay was great

Reviewed on Jun 13, 2026

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Save 100% on your flight
Price was $2,772, price is now $2,096 per person
$2,096
per person
Jul 14 - Jul 19
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
10/10 Exceptional! (1 review)
Such a beautiful time was spent here with my family for my nephews graduation from university at Albany. We feed the birds, played family games, got in the hot tub.

Reviewed on May 23, 2026

The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $1,249, price is now $953 per person
$953
per person
Jul 14 - Jul 19
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (1,011 reviews)
The room was large, clean and comfortable. The location was near shopping and dining. The check in was quick and pleasant.

Reviewed on Jun 11, 2026

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3 out of 5
Save 100% on your flight
Price was $3,708, price is now $2,834 per person
$2,834
per person
Jul 14 - Jul 19
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
No reviews
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,985, price is now $1,566 per person
$1,566
per person
Jul 14 - Jul 19
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.8/10 Exceptional! (29 reviews)
5/5 stars! Great experience, beautiful property, and super nice and helpful staff. The farm to table food at the cliff house restaurant was amazing. 100% coming back to this property

Reviewed on Apr 28, 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
$115 nightly
The price is $129 total per night from Jun 21 to Jun 22
$129 total
Jun 21 - Jun 22
Total with taxes and fees
7.4/10 Good! (1,009 reviews)
"First Lady at the desk was rude and dismissive from the start and straight up walked away without saying anything. This then turned into a 25-30 minute wait with nobody at the front desk to assist. When the lady eventually came back, she had an even crappier attitude. The second guy (Kevin) was a ..."

Reviewed on Jun 1, 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 Jul 13 to Jul 14
$226 total
Jul 13 - Jul 14
Total with taxes and fees
9.6/10 Exceptional! (248 reviews)
"We had a wonderful weekend stay at Postcard Cabins in the Eastern Catskills. The cabin was peaceful, cozy, and exactly what we needed for a relaxing getaway. One of our favorite parts was spending the evenings making s’mores and enjoying the tranquility of the surrounding nature. The host provided ..."

Reviewed on Jun 13, 2026

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

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$181 nightly
The price is $202 total per night from Jul 9 to Jul 10
$202 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (515 reviews)
"We stayed in the cabin, very spacious, clean, the bed is so comfortable. The staffs in the center are very friendly and helpful."

Reviewed on Jun 10, 2026

AutoCamp Catskills
See all 2,007 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 $713 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.