Rye Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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    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.
Westchester Marriott

Westchester Marriott

4.5 out of 5
Price was CA $1,217, price is now CA $996 per person
CA $996
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9/10 Wonderful! (675 reviews)

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $2,786, price is now CA $2,118 per person
CA $2,118
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)

Delamar Southport

Delamar Southport

4 out of 5
Price was CA $2,246, price is now CA $1,748 per person
CA $1,748
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
9.6/10 Exceptional! (522 reviews)
No complaints great location and clean

Reviewed on Nov 3, 2026

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
Price was CA $2,068, price is now CA $1,685 per person
CA $1,685
per person
Dec 21 - Dec 27
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
6.2/10 (197 reviews)

Delamar Westport

Delamar Westport

4 out of 5
Price was CA $2,562, price is now CA $2,101 per person
CA $2,101
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
9.6/10 Exceptional! (189 reviews)

Ready to book your vacation to Rye?

 

Choose your dates

Rye Hotel Deals

Park Lane New York

Park Lane New York

5 out of 5
36 Central Park S New York NY
Fully refundableReserve now, pay when you stay
The price is CA $686 per night from Nov 22 to Nov 23
CA $686
CA $872 total
Nov 22 - Nov 23
includes taxes & fees
8.4/10 Very good! (1,854 reviews)
"I have stayed in many rooms at The Park Lane all very good. The view in the front big rooms are amazing but if you truly love quite like I do the rooms in the back along the side are so quite. The beds are great king beds and the staff amazing."

Reviewed on Nov 13, 2026

Park Lane New York
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
215 W 94th St New York NY
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Nov 22 to Nov 23
CA $169
CA $227 total
Nov 22 - Nov 23
includes taxes & fees
7.6/10 Good! (137 reviews)
"Good location , one night stay for work , perfect spot to stay , i don’t understand some review not positive , this is New York not a all inclusive resort at Bahamas! Thank you! See you again"

Reviewed on Nov 14, 2026

Night Hotel Broadway
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 $174 per night from Nov 22 to Nov 23
CA $174
CA $238 total
Nov 22 - Nov 23
includes taxes & fees
Empire Hotel
See all 4,340 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
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Stay near popular Rye attractions

Rye Playland

8.2/10 (33 reviews)
Have a fun-filled day with the family at Rye Playland during your visit to Rye. Discover the live music in this family-friendly area, or seek out its hiking trails.
See properties

Frequently asked questions

How much does a Rye vacation package cost?
You can snap up a vacation package to this top destination from CA $996 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.