An aerial view of a golf course with sand bunkers and trees.

Rye Brook Vacations from $487

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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 Rye Brook Vacation

Say goodbye to planning worries and hello to a Rye Brook vacation package. With everything organized before you take off, you can focus on discovering the best of this city, starting with Downtown Stamford, which is good for history, bars and pubs and dining. Capitol Theatre, Westchester County Center and The Westchester Mall are just some of the many attractions worth exploring during your trip to Rye Brook. Expedia has what you need to escape your routine. Tailor your vacation to Rye Brook to match your travel style, whatever that may look like.

The Latest Rye Brook Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 11 - Jan 15

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    4 nights
    4.0 star property
    9.0/10 - Wonderful (3,464 reviews)
    "My second time staying here and it never disappoints. Very clean, comfortable and attentive staff."
    Reviewed November 9, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - EWR • Nonstop LGA - ATL • Nonstop
    $850
    $487
    per traveler
    found 2 days ago
    Hotel Riu Plaza New York Times Square
  • Jan 11 - Jan 15

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    4 nights
    4.0 star property
    9.2/10 - Wonderful (4,165 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - EWR • Nonstop LGA - ATL • Nonstop
    $885
    $504
    per traveler
    found 2 days ago
    Hotel Riu Plaza Manhattan Times Square
  • Jan 20 - Jan 24

    JW Marriott Essex House New York + Flight

    Manhattan
    4 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    $1,529
    $888
    per traveler
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 22 - Jan 24

    1 Hotel Brooklyn Bridge + Flight

    Brooklyn
    2 nights
    5.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    "Incredible views, ambiance, staff, and overall experience! The only thing to note is that it can be quite loud since you're right on the waterfront and the ferries and boats sound their horns frequently"
    Reviewed November 8, 2026
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - LGA • Nonstop EWR - ATL • Nonstop
    $1,083
    $636
    per traveler
    found 22 hours ago
    1 Hotel Brooklyn Bridge
  • Jan 16 - Jan 22

    Loews Regency New York Hotel + Flight

    Manhattan
    6 nights
    5.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip • Atlanta (ATL) - New York (JFK)
    ATL - JFK • Nonstop JFK - ATL • Nonstop
    $2,547
    $1,504
    per traveler
    found 1 day ago
    Loews Regency New York Hotel

Where to stay in and around Rye Brook

Rye Brook offers a delightful travel experience with its family-friendly atmosphere and cultural charm. Explore nearby attractions from the Rye Brook Center and enjoy the vibrant vibes just miles from New York City, making it an ideal destination for outdoor adventures and family fun.

Port Chester

Discover Port Chester, a welcoming destination perfectly suited for travelers seeking a blend of culture and entertainment. This vibrant village offers access to charming spots like Greenwich Avenue for shopping, the thrilling rides at Rye Playland, and engaging events at the Westchester County Center. Located in Rye Brook, Port Chester provides easy transit options, making it a smart choice for your stay. Enjoy a memorable experience in this dynamic area that caters to both families and weekend getaway seekers.

Purchase

Experience the charm of Purchase, a perfect hub for families and weekend getaway travelers eager to explore cultural and educational attractions. Just a short distance from Rye Brook, Purchase offers access to the Westchester County Center, renowned for its vibrant arts scene, and Purchase College, an impressive modern university. Visitors can also enjoy the lively atmosphere of Greenwich Avenue, making it a delightful choice for your stay. With its appealing mix of activities, Purchase is a smart hotel booking choice for your vacation.

Rye

If you are a family traveler, look no further than Rye, a charming city known for its delightful blend of outdoor activities and entertainment. You can enjoy a day at Rye Playland amusement park or take in a show at the Westchester County Center, all while exploring the scenic Greenwich Avenue. Located about 3 miles by car from Rye Brook, this area offers a smart choice for your hotel booking, ensuring easy access to memorable experiences.

Greenwich

Ideally situated for family vacations and weekend getaways, Greenwich offers a vibrant mix of outdoor activities and city experiences. Travelers can enjoy shopping along Greenwich Avenue, explore the fun at Rye Playland, or catch a show at the Westchester County Center. With its diverse attractions, Greenwich makes for an appealing choice, located about 3 miles by car from Rye Brook. This charming city is a smart pick for a memorable stay.

Greenwich Municipal Center Historic District

Travelers seeking a vibrant city experience will find the Greenwich Municipal Center Historic District to be the ideal base for their vacation, featuring a charming mix of shopping, entertainment, and local culture. Just a short drive from Rye Brook, this neighborhood offers attractions like Greenwich Avenue for shopping, the family-friendly Rye Playland amusement park, and the Westchester County Center for arts events. With its convenient access to lively venues and activities, the Greenwich Municipal Center Historic District is a smart choice for your stay.

Discover the most popular places to visit in Rye Brook

What to do in Rye Brook

Rye Brook Hotel Deals

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.

Frequently Asked Questions

How much does a Rye Brook vacation package cost?

Offering great value package deals from $487 on Expedia, you'll be thrilled with how little a vacation to Rye Brook costs! Expedia's packages make travel planning easier and save you more.

What are the cheapest months to go to Rye Brook?

If you're looking to snag a cheap Rye Brook vacation package, consider visiting in February, September and October. You'll typically find better rates on hotels and airfares during these months — perfect for a budget-friendly break.

How many days is enough for Rye Brook?

You can easily see all the major sights in Rye Brook in a few days, including the must-see Clay Art Center Gallery. If you're looking for a longer Rye Brook vacation, check out what kind of excursions and activities are available in the area.

Is it worth booking a vacation package to Rye Brook?

Rye Brook has everything you need for an unforgettable trip. Get your Rye Brook vacation off to a flying start by checking out major attractions like Capitol Theatre.

How to find the best Rye Brook package deals?

Start your search for a Rye Brook package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Rye Brook package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Rye Brook escape underway.

Is it cheaper to book a Rye Brook vacation as a package?

An Expedia vacation package could score you significant savings when compared to booking stays and flights individually. Better still, you can tailor your Rye Brook getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.

When to book a vacation package to Rye Brook?

Land incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Rye Brook break.

How to plan a trip to Rye Brook?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Rye Brook.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will probably be the biggest expense during your trip to Rye Brook.
  3. Organize your Rye Brook getaway with Expedia's trip planning tool: Search for and book accommodations and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Rye Brook together.
  4. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Rye Brook. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Rye Brook vacation package that brings all your bookings together.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to see and do. Check out some of the best things to do in Rye Brook and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Rye Brook vacation packages?

Your Rye Brook break is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.