Rye Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by athena macone

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Your Rye Vacation

Reserve a Rye vacation package and get ready to experience all this city has to offer. Consider staying in the neighborhood of Downtown Stamford, which is great for history, bars and pubs and dining. Like to explore your new surroundings? Capitol Theatre, The Westchester Mall and Rye Playland are among the most popular places to visit during a trip to Rye. Whatever your travel plans or budget, organizing a tailored Rye vacation is a walk in the park with Expedia.

Top Rye Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Stamford Hotel & Executive Meeting Center

Hilton Stamford Hotel & Executive Meeting Center

3.5 out of 5
Waterside
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
7.4/10 Good! (1,008 reviews)
Very pleasant stay. Staff was kind and polite. Clean and comfortable room. We had a wonderful time

Reviewed on Aug. 3, 2025

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
2/10 (1 review)
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
8.6/10 Excellent! (1,107 reviews)
Everything was fantastic bed was super comfy. Great room service. Only issue, one of the pool attendants vomited into a poolside waste paper basket as I started swimming around 9pm night before I checked out, he left it there said nothing then rested on the job, I immediately went to my room. In all my years that's never happened before. I felt more could have been done by the hotel to apologize.

Reviewed on Aug. 3, 2025

2 Cabins w/ Hot Tub, Pool, Firepit, & Outdoor Dining Minutes From Wineries

2 Cabins w/ Hot Tub, Pool, Firepit, & Outdoor Dining Minutes From Wineries

3 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
No reviews
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
8/10 Very Good! (1,085 reviews)
Great place to stay. Breakfast was good. Easy access to Highways.

Reviewed on Aug. 5, 2025

Ready to book your vacation to Rye?

 

Choose your dates

Rye Hotel Deals

Empire Hotel

Empire Hotel

4 out of 5
44 W 63rd St, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 17 to Aug 18
CA $202
CA $268 total
Aug 17 - Aug 18
includes taxes & fees
7.6/10 Good! (5,758 reviews)
"Loved it all. Great experience!"

Reviewed on Aug. 4, 2025

Empire Hotel
Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
215 W 94th St, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Aug 10 to Aug 11
CA $146
CA $200 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (2,257 reviews)
"Easy checkin."

Reviewed on Aug. 2, 2025

Night Hotel Broadway
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
540 Park Avenue, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $770 per night from Aug 7 to Aug 8
CA $770
CA $891 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"The room was a little tired and could have used some fresher furniture"

Reviewed on Aug. 2, 2025

Loews Regency New York Hotel
See all 4,070 properties in Rye
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Rye vacation package cost?
You can snap up a vacation package to this top destination from CA $703 on Expedia. But how much your vacation to Rye costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Rye?
If you're looking to snag a cheap Rye vacation package, consider planning a trip in January, February and March. You'll generally find better prices on flights and accommodations during these months — perfect for travellers wishing to save money.
How many days is enough for Rye?
You can easily explore all the leading attractions in Rye within a few days, including the popular The Westchester Mall. If you're after a longer Rye vacation, look at what kind of activities and day tours are available close by.
Is it worth booking a vacation package to Rye?
Rye offers everything you need for an unforgettable escape. Get your Rye vacation off to a flying start by checking out top attractions like Rye Playland.
How to find the best Rye package deals?
Landing a cheap Rye package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most pocket-friendly Rye package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Rye vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can personalize your Rye escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Rye?
If you're considering a spur-of-the-moment Rye adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Rye?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite season and the type of activities available will also help you decide when to vacation in Rye.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the largest expense during your trip to Rye.
  3. Work out your trip length: Think about how long you'd like to spend exploring Rye. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the right Rye 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.