Red Hook Vacations from $411

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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.
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $531, price is now $411 per person
$411
per person
Jan 9 - Jan 11
found 20 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,316, price is now $844 per person
$844
per person
Dec 27 - Dec 31
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (8 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $788, price is now $597 per person
$597
per person
Dec 31 - Jan 4
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
18/10 Exceptional! (215 reviews)
Room spotless. However no cups in bathroom. Wine chiller did not work and had to be replaced. Also had to request clothing hangers for clothing. Only two hangers were in room.

Reviewed on Nov 9, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $922, price is now $716 per person
$716
per person
Jan 29 - Feb 1
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
14.8/10 Exceptional! (567 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.

Reviewed on Oct 27, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,603, price is now $1,245 per person
$1,245
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Albany (ALB)
19.2/10 Exceptional! (11 reviews)
Great property. Amazing views!

Reviewed on Dec 2, 2024

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Discover the most popular places to visit in Red Hook

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
$106 nightly
The price is $118 total per night from Dec 1 to Dec 2
$118 total
Dec 1 - Dec 2
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
The room was great—clean. The restaurant was great—the food was tasty. The staff was exemplary. I would definitely stay here again.

Reviewed on Nov 11, 2025

Best Western Plus Kingston Hotel And Conference Center
Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
7 Terwilliger Ln New Paltz NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $106 total per night from Dec 9 to Dec 10
$106 total
Dec 9 - Dec 10
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
Excellent

Reviewed on Nov 11, 2025

Americas Best Value Inn New Paltz
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
$88 nightly
The price is $99 total per night from Nov 23 to Nov 24
$99 total
Nov 23 - Nov 24
Total with taxes and fees
7.6/10 Good! (924 reviews)
Very clean and modern hotel for the price. Safe area, very comfortable beds, large rooms. Stayed here before and forgot, when we pulled up we were excited. We remembered how great it was! Definitely would stay again. Not far from New Paltz so a great choice if closer hotels are booked. Worth the ...

Reviewed on Nov 14, 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
See all 1,978 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 $411 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.