Red Hook Vacations from $443

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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 $596, price is now $443 per person
$443
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Although the bed was comfortable the room overall needed help. There were cosmetic issues, like pealing paint and cobwebs in the fireplace.

Reviewed on Dec 11, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,089, price is now $721 per person
$721
per person
Feb 13 - Feb 16
found 10 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $771, price is now $551 per person
$551
per person
Feb 13 - Feb 16
found 10 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $1,541, price is now $1,109 per person
$1,109
per person
Feb 19 - Feb 23
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this by repairing or replacing that door that leads outside. There’s a 1 inch gap there. Also, while this is an issue, close those 2 inside doors. That works.

Reviewed on Dec 7, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $807, price is now $613 per person
$613
per person
Feb 13 - Feb 16
found 10 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The Inn was very nice and the staff was super friendly and attentive.

Reviewed on Dec 12, 2025

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Discover the most popular places to visit in Red Hook

Old Rhinebeck Aerodrome

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

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Dec 28 to Dec 29
$108 total
Dec 28 - Dec 29
Total with taxes and fees
7.6/10 Good! (498 reviews)
Room was clean. Staff was kind. Good complimentary breakfast

Reviewed on Nov 23, 2025

Quality Inn Poughkeepsie
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $128 total per night from Dec 21 to Dec 22
$128 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (790 reviews)
Everything was great. Fantastic breakfast. Fire alarm went off the first night we were there and we had to wait till that was over but other than that everything was good

Reviewed on Dec 8, 2025

Residence Inn by Marriott Kingston
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 out of 5
4 South Putt Corners Road New Paltz NY
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $128 total per night from Jan 4 to Jan 5
$128 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Very convenient to bike the Empire Rail Trail, and attached trail. Staff was friendly and helpful. It was a clean, safe environment. Local eateries were good.

Reviewed on Dec 12, 2025

Hampton Inn by Hilton New Paltz
See all 1,971 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 $443 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.