Tarrytown Vacations from $317

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $761, price is now $317 per person
$317
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16/10 Exceptional! (1,367 reviews)
from the staff to the clean rooms and all the fun things in the resort... WAS GREAT!!!!

Reviewed on Nov 18, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,896, price is now $625 per person
$625
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.2/10 Exceptional! (1,002 reviews)
Clean room expected amenities

Reviewed on Nov 12, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $1,249, price is now $429 per person
$429
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (2,232 reviews)
We had a great time.

Reviewed on Nov 20, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,098, price is now $439 per person
$439
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too! When we come back to visit, we will definitely rebook at the Shores!!!

Reviewed on Nov 16, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,631, price is now $696 per person
$696
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (1,001 reviews)
The place is exceptional and met all of our needs and then some

Reviewed on Nov 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to Tarrytown
View all trips

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

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 Nov 23 to Nov 24
$94 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Absolutely

Reviewed on Nov 10, 2025

Microtel Inn & Suites by Wyndham Brooksville
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 Nov 23 to Nov 24
$83 total
Nov 23 - Nov 24
Total with taxes and fees
7/10 Good! (1,004 reviews)
For the price it was very good. Older property but clean and staff was courteous. Breakfast was good.

Reviewed on Nov 9, 2025

Days Inn by Wyndham Brooksville/Dade City
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
$76 nightly
The price is $81 total per night from Nov 23 to Nov 24
$81 total
Nov 23 - Nov 24
Total with taxes and fees
7.4/10 Good! (897 reviews)
Best beds ever, best night sleep in a hotel!

Reviewed on Nov 14, 2025

Microtel Inn & Suites by Wyndham Bushnell
See all 771 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Tarrytown vacation package cost?
Offering great value package deals from $317 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.