Red Hook Vacation Packages
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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.
Top Red Hook Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
CA $637
per person
Oct 28 - Oct 31
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
8.8/10 Excellent! (2,503 reviews)
Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded.
Reviewed on Aug 11, 2026
The Cornell Inn, Lenox & The Berkshires
CA $875
per person
Oct 28 - Oct 31
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
We booked a queen room. When we arrived, we were told the AC in our room had stopped working and were given a fan. We were shown to a room with a king bed and later found out our room had been given to another guest who had booked the king room because of the broken AC. We had a terrible nights sleep. We were told a manager would email or call us to refund part of our stay for the inconvenience.
Things that could have been done better.
1) notify guests if there is a problem so they can make other accommodations. We arrived at 6 pm for an 8 pm event and could not make last minute arrangements.
2) Honor guest reservations rather than giving rooms away to preferential guests. No explanation was given for why our room with functioning AC was given away.
3) Make an effort to go buy a window AC or keep one on hand for emergencies.
4) Managers should follow up on poor experiences and refund guests as promised by staff.
Reviewed on Aug 10, 2026
Berkshire Mountain Lodge
CA $647
per person
Oct 28 - Oct 31
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (1,041 reviews)
Unfortunately, (my wife informed me as she was the traveler) there was NO shower curtain; and the a/c needed a tech to get it working properly. This hasn't been our experience with this nice property in the past. Just bad luck on the room assignment this time, I guess...
Reviewed on Aug 11, 2026
Ready to book your vacation to Red Hook?
Red Hook Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
CA $171
CA $193 total
Aug 16 - Aug 17
includes taxes & fees
8.2/10 Very good! (965 reviews)
"The hotel looks a little tired. Could use significant upgrades. It would also be a lot better if breakfast was served in a hotel,rather than over a block away."
Reviewed on Aug 11, 2026
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $149
CA $174 total
Aug 20 - Aug 21
includes taxes & fees
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
CA $124
CA $139 total
Aug 26 - Aug 27
includes taxes & fees
8/10 Very good! (1,016 reviews)
"Staff was very nice and helpful. The hotel needs to limit smoking at the entrances, including staff. For the price of a night, you can stay elsewhere that is much cleaner with all working amenities."
Reviewed on Aug 11, 2026
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.
Stay near popular Red Hook attractions
Old Rhinebeck Aerodrome
9.4/10 (8 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.
Poet's Walk Park
10.0/10 (2 reviews)
Explore the great outdoors at Poet's Walk Park, a lovely green space in Red Hook. Experience the area's festivals and entertainment venues.
Red Hook Golf Club
Enjoy a round of golf in Red Hook at Red Hook Golf Club. Stroll along the marina or experience the area's festivals.
Lake Carvel
Commune with nature and explore the great outdoors at Lake Carvel during your travels in Red Hook. Stroll along this romantic area's lakeside, or simply enjoy its coffeehouses.
Frequently asked questions
How much does a Red Hook vacation package cost?
You can snap up a vacation package to this destination from CA $637 on Expedia. But how much your vacation to Red Hook costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Red Hook?
The off-season is the best time to head to Red Hook if you're trying to keep costs down. Another tip for getting cheap Red Hook vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Red Hook?
To fully enjoy your Red Hook vacation, we suggest staying for 3 days. Split your time between visiting Saugerties Lighthouse, Centre for Performing Arts at Rhinebeck and other leading sights, on top of experiencing neighbourhoods like Saugerties South and Town of Clermont. If you've got some time to spare, add a day trip or tour to your Red Hook vacation itinerary.
Is it worth booking a vacation package to Red Hook?
Red Hook has all the ingredients you need for an amazing trip — walking trails, history and golfing are just the start. Whether you want to check out attractions like Old Rhinebeck Aerodrome and Poet's Walk Park, or venture off the beaten track, there's plenty to see and do on your Red Hook vacation.
How to find the best Red Hook package deals?
Bagging a cheap Red Hook package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Red Hook package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Red Hook vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can tailor your Red Hook getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Red Hook?
Land amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Red Hook trip.
How to plan a trip to Red Hook?
- Choose when to go: Check your schedule and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit Red Hook.
- Budget wisely: On top of the price of your hotel, you'll need to consider other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may arise during your trip to Red Hook.
- Determine how many days away: Start by listing all the activities and sights you'd like to get to in Red Hook. Then, estimate how long you'll need at each, along with any travel time.
- Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the right Red Hook vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
