Tarrytown Vacations from $309

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Your Tarrytown Vacation

Enjoy amazing adventures when you book a Tarrytown vacation package. Whether you're a history buff, art enthusiast or just a traveler who loves experiencing new places, there's something for everyone in this interesting city. Eager to do a little sightseeing? Spend some time enjoying well-known attractions like Webster Westside Flea Market during your trip to Tarrytown. Don't delay your visit to this city any longer. The ultimate Tarrytown vacation is only a few clicks away with Expedia.

The Latest Tarrytown vacation packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,152, price is now $309 per person
$309
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
Beautiful place to stay.

Reviewed on Dec 14, 2025

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,589, price is now $582 per person
$582
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,433, price is now $559 per person
$559
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.

Reviewed on Nov 30, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,007, price is now $444 per person
$444
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
Clean room. Exceptional service from all the staff each day. Amazing amenities. And gorgeous views.

Reviewed on Dec 14, 2025

I-Drive Hotel at Universal

I-Drive Hotel at Universal

2.5 out of 5
International Drive District
Price was $852, price is now $404 per person
$404
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
6.8/10 (1,002 reviews)
Staff were fantastic

Reviewed on Dec 12, 2025

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Discover the most popular places to visit in Tarrytown

Webster Westside Flea Market

You can do some window-shopping at Webster Westside Flea Market during your trip to Webster. You can enjoy the coffeehouses while in the area.

Webster Westside Flea Market

Tarrytown Hotel Deals

Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

2 out of 5
6320 Windmere Rd Brooksville FL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Dec 18 to Dec 19
$83 total
Dec 18 - Dec 19
Total with taxes and fees
7/10 Good! (1,001 reviews)
The room was clean and confortable.

Reviewed on Dec 9, 2025

Days Inn by Wyndham Brooksville/Dade City
Microtel Inn & Suites by Wyndham Brooksville

Microtel Inn & Suites by Wyndham Brooksville

2 out of 5
6298 Nature Coast Blvd Brooksville FL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Dec 21 to Dec 22
$94 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
Easy check in! Room was clean, got a room on the second floor and you can hear the people walking on the room above, other than that no complaints for the price.

Reviewed on Dec 14, 2025

Microtel Inn & Suites by Wyndham Brooksville
Microtel Inn & Suites by Wyndham Bushnell

Microtel Inn & Suites by Wyndham Bushnell

2 out of 5
2612 West County Road 48 Bushnell FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $76 total per night from Dec 18 to Dec 19
$76 total
Dec 18 - Dec 19
Total with taxes and fees
7.4/10 Good! (931 reviews)
It was a clean and adequate and convenient place to stay with good service

Reviewed on Dec 9, 2025

Microtel Inn & Suites by Wyndham Bushnell
See all 781 properties in Tarrytown
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 Tarrytown Vacation Packages

Tarrytown Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Tarrytown vacation package cost?
Offering great value package deals from $309 on Expedia, you'll be surprised at how little a vacation to Tarrytown costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Tarrytown?
June, July and October are great times to search for cheap Tarrytown vacation packages. Opting to travel in quieter months means you can generally find reduced prices on accommodations and flights.
How many days is enough for Tarrytown?
Typically, a handful of days is enough to check out the main sights during your Tarrytown vacation. But if you want to have time to kick back or take day tours, consider extending your itinerary.
How to find the best Tarrytown package deals?
Finding a cheap Tarrytown package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most affordable Tarrytown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Tarrytown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still have the freedom to create a personalized Tarrytown vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Tarrytown?
If you have your Tarrytown vacation dates confirmed, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Tarrytown vacation packages?
Your Tarrytown getaway is meant to be a relaxing escape from your busy life, not a source of money worries. So to allow you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.