Trilcoochee Vacations from $620

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Your Trilcoochee Vacation

Lock in a custom vacation package to Trilcoochee and get ready for your next big adventure. Stay in the neighborhood of Tarrytown, which is good for camping and families, for a true taste of this lively city. There's plenty to do and see during your trip to Trilcoochee, including Giraffe Ranch and Pioneer Florida Museum & Village. Whatever your travel plans or the size of your budget, putting together a tailored Trilcoochee vacation is a cinch with Expedia.

The Latest Trilcoochee vacation packages

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

Central Sarasota
Save 100% on your flight
$620
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,007 reviews)
Clean nice location

Reviewed on Aug 14, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

Save 100% on your flight
$879
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (568 reviews)
Had an amazing time. Clean rooms, friendly staff. Amazing amenities with having use of beach chairs and umbrellas. Will return next summer.

Reviewed on Aug 13, 2026

CW Hotel

CW Hotel

Save 100% on your flight
$990
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (48 reviews)
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight
$629
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,341 reviews)
Luckily, I was upgraded to a Harbor view beautiful room clean definitely recommend

Reviewed on Aug 13, 2026

The Westin Sarasota

The Westin Sarasota

Central Sarasota
$627
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,151 reviews)
My only gripe was the lack of an ocean view, had a view of the harbor/bay, which wasn’t bad, but was hoping for more

Reviewed on Aug 14, 2026

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Trilcoochee Hotel Deals

Saddlebrook Resort

Saddlebrook Resort

5700 Saddlebrook Way Wesley Chapel FL
Fully refundableReserve now, pay when you stay
$169 nightly
$189 total
Sep 14 - Sep 15
Total with taxes and fees
8/10 Very Good! (150 reviews)
"resort was beautiful, great food, staff, were all were pleasant and helpful. very much what to expect from a resort"

Reviewed on Aug 13, 2026

Saddlebrook Resort
Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

6320 Windmere Rd Brooksville FL
Fully refundableReserve now, pay when you stay
$67 nightly
$75 total
Sep 1 - Sep 2
Total with taxes and fees
Days Inn by Wyndham Brooksville/Dade City
SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

5703 Oakley Blvd Wesley Chapel FL
Fully refundableReserve now, pay when you stay
$98 nightly
$110 total
Aug 23 - Aug 24
Total with taxes and fees
SPOT X Hotel Tampa - Wesley Chapel by The Red Collection
See all 408 properties in Trilcoochee
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 Trilcoochee Vacation Packages

Trilcoochee Essential Information

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Frequently asked questions

How much does a Trilcoochee vacation package cost?
You'll find cheap prices from $620 on Expedia for your Trilcoochee break. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Trilcoochee costs.
What are the cheapest months to go to Trilcoochee?
If you'd like to book a cheap Trilcoochee vacation package, consider planning a trip in May, July and August. You'll typically find lower prices on hotels and flights during these months — ideal for travelers wishing to save money.
How many days is enough for Trilcoochee?
The ideal duration of your Trilcoochee vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to visit all the top attractions and discover some hidden gems along the way.
How to find the best Trilcoochee package deals?
Begin your search for a Trilcoochee package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Trilcoochee package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Trilcoochee adventure off to a flying start.
Is it cheaper to book a Trilcoochee vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can personalize your Trilcoochee getaway to match your exact style. Pick 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 Trilcoochee?
Secure fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Trilcoochee vacation.
Does Expedia offer Book Now, Pay Later Trilcoochee vacation packages?
Your Trilcoochee break should be an escape from your daily routine, not a reason for money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.