Rye Vacations from $264

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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.

The Latest Rye vacation packages

Price found within the past 48 hours. Click for updated prices.
Royal Regency Hotel
Hotel NoMa, Trademark Collection by Wyndham
Hampton Inn White Plains/Tarrytown
Days Inn by Wyndham Elmsford / White Plains
Quality Inn Poughkeepsie
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Discover the most popular places to visit in Rye

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
$260 nightly
The price is $302 total per night from Sep 2 to Sep 3
$302 total
Sep 2 - Sep 3
Total with taxes and fees
7.6/10 Good! (5,831 reviews)
"I enjoyed having plenty of staff on hand in the lobby keeping the hotel safe and clean. I also enjoyed having some access to the roof top to enjoy the views of the city. Loved having the outdoor space across from the hotel where you could sit in a park setting and enjoy a cup of coffee on clean benches ..."

Reviewed on Aug 24, 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
$168 nightly
The price is $196 total per night from Aug 27 to Aug 28
$196 total
Aug 27 - Aug 28
Total with taxes and fees
7/10 Good! (2,318 reviews)
"Though they could not match the price I attained through this third party site, the hotel did have accommodations and I felt safe."

Reviewed on Aug 22, 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
$559 nightly
The price is $647 total per night from Sep 1 to Sep 2
$647 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Location is best im America. EVERYTHING is right there. Staff is extremely attentive and excellent workers. They found all kind of perks and things to offer us. Truly above and beyond. The property is older; needs renovations to bring it to 22 st century with period details. Our compliments to all ..."

Reviewed on Aug 16, 2025

Loews Regency New York Hotel
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.

Things to do in and around Rye

Rye, New York, is perfect for family-friendly vacations with plenty of outdoor and entertainment options. Visitors can enjoy local theater, explore amusement parks, and shop in charming areas. Don't miss the chance to discover Rye through travel guides and plan a memorable day trip filled with recreation opportunities and welcoming attractions for everyone.

Shopping

In Rye, you can enjoy shopping at The Westchester Mall, just 5 miles away, featuring a mix of entertainment and family-friendly vibes. If you're up for a drive, Westchester's Ridge Hill is 9 miles away, offering a vibrant atmosphere. For a unique experience, visit Rockland Bakery, located 18 miles from Rye.

Recreation

Yankee Stadium, located 16 miles from Rye, offers an exhilarating sports atmosphere perfect for fans. The Capitol Theatre, just 2 miles away, provides a cultural experience with its romantic ambiance and diverse entertainment options. For outdoor enthusiasts, Westchester Country Club invites you to enjoy golf in a scenic setting.

Adventure

Experience the excitement at Legoland Discovery Center Westchester, located 9 miles from Rye, where you can explore interactive rides and creative play areas. New Roc n Bowl, 7 miles away, offers bowling and arcade fun for the whole family. Sportime USA, also 9 miles away, features thrilling games and attractions.

Nightlife

For an exciting night out in Rye, consider visiting the Stonewall Inn, a lively pub with a romantic vibe located 24 miles away. Alternatively, enjoy the fun atmosphere at Dave & Buster's, just 22 miles from Rye, or head to 51-53 Christopher Street for more vibrant nightlife options.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Rye

Rye, New York, offers a family-friendly vacation experience with a focus on outdoor activities and entertainment. Visitors can explore urban parks, local colleges, and beautiful beaches, including Rye Beach and Rye Harbour. Notable attractions like Lookout Rye provide cultural insights and fun for all ages, making it an ideal destination for travelers seeking both relaxation and adventure.

  • Rye Playland: Experience the thrill at Rye Playland, a charming amusement park that offers a variety of rides and attractions perfect for families. Enjoy the outdoor atmosphere and adventure vibes while making memories on the iconic Dragon Coaster or relaxing by the waterfront.
  • Westchester County Center: Immerse yourself in culture at the Westchester County Center, located 6 miles away. This arts center hosts a variety of events, from concerts to exhibitions, making it a vibrant hub for art enthusiasts and visitors alike.
  • Greenwich Avenue: Stroll down Greenwich Avenue, located 4 miles away, and soak in the lively city vibes. This bustling street is lined with shops, cafes, and restaurants, perfect for a leisurely afternoon of shopping and dining.

Tips to save on your trip to Rye

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Rye.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Rye.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Rye vacation package cost?
You can snap up a vacation package to this popular destination from $264 on Expedia. But how much your vacation to Rye costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Rye?
You can usually find lower prices and greater availability in December, January and February. Browse our cheap Rye vacation packages and you could get some excellent off-season deals.
How many days is enough for Rye?
You can easily visit all the main attractions in Rye within a few days, including the must-see Jay Heritage Center. If you're looking for an extended Rye vacation, look at which kind of activities and day trips are available nearby.
Is it worth booking a vacation package to Rye?
Rye is a good vacation destination with attractions like Rye Playland among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Rye vacation promises a good time for everyone.
How to find the best Rye package deals?
Start your search for a Rye package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Rye package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Rye adventure off to a flying start.
Is it cheaper to book a Rye vacation as a package?
You can enjoy significant savings on your next Rye retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Rye?
Enjoy incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Rye trip.
Does Expedia offer Book Now, Pay Later Rye vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Rye break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.