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.
South Shire
CA $1,463
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (131 reviews)
The property and room itself was a nice space, and a good location, very quiet. It needed a little more care in the cleaning (some dusty areas along the baseboards and under tables). No one came to clean or check on the room during our two night stay. The self-serve property app - to check in and communicate with the staff - could not be accessed (an authentication issue due to our booking through Expedia and not directly with the property). We luckily ran into a staff member at check in who could get our keys. They were clear that this is a small operation with limited staff - but still. We kinda felt no love.
Reviewed on Sep 2, 2026
Aspen At Manchester
CA $1,297
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (683 reviews)
Didn't like that the bathroom shower had no soap dish or any kind of shelf for shampoos and stuff. The room was very musty smelling even with the A/C on. Room was clean and any staff we did run across was friendly. Don't like the idea if you arrive early they want to charge $35 extra. If the room is empty why? Don't think the price justify's what you get or don't get.
Reviewed on Sep 10, 2026
Brook Bound Inn
CA $1,582
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 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 $185
CA $210 total
Sep 14 - Sep 15
includes taxes & fees
8.2/10 Very good! (1,005 reviews)
"my only complaint was that check-in and parking were a bit opaque - hard to know where to park mostly."
Reviewed on Sep 11, 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
CA $222
CA $299 total
Sep 15 - Sep 16
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 $123
CA $138 total
Sep 27 - Sep 28
includes taxes & fees
8/10 Very good! (1,017 reviews)
"I frequently stay there"
Reviewed on Sep 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 relaxing 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 $537 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.
