Bloomington Vacations from $832
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Your Bloomington Vacation
Say farewell to the hassle of planning and hello to a Bloomington vacation package. With the finer details organized before you leave, you can focus on discovering the best of this city, starting with Kingston Stockade District, which is great for families, festivals and markets. Make your trip to Bloomington even more fun by going sightseeing. Ulster Performing Arts Center, Esopus Creek and Senate House State Historic Site are some of the leading attractions worth exploring. No matter your travel plans or budget, putting together the ultimate tailored Bloomington vacation is a walk in the park with Expedia.
The Latest Bloomington vacation packages
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
$1,238
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.
Reviewed on Aug 21, 2026
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Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$101 nightly
$117 total
Sep 7 - Sep 8
Total with taxes and fees
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$189 nightly
$214 total
Aug 31 - Sep 1
Total with taxes and fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
$95 nightly
$110 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
"No comments"
Reviewed on Aug 21, 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.
Find the Best Bloomington Vacation Packages
Bloomington Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Top Sights | Ulster Performing Arts Center, Kingston Point Beach and Walnut Beach |
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Frequently asked questions
How much does a Bloomington vacation package cost?
You'll find cheap prices from $832 on Expedia for your Bloomington getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Bloomington costs.
What are the cheapest months to go to Bloomington?
November, December and January are great times to search for cheap Bloomington vacation packages. Choosing to travel in less busy months means you can generally find better prices on accommodations and flights.
How many days is enough for Bloomington?
Typically, a handful of days is enough to check out the main attractions during your Bloomington vacation. But if you'd like to have more time to kick back or go on day trips, think about extending your itinerary.
How to find the best Bloomington package deals?
Use Expedia's filter tool to help you find some fabulous Bloomington package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Bloomington package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Bloomington vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Bloomington vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Bloomington?
If you've got your Bloomington travel dates finalized, book early to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Bloomington vacation packages?
If you're anything like us, you love traveling but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Bloomington break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
