Rye Brook Vacations from $274

Book a Hotel + Flight or Car together to unlock savings

Photo by gavvykins

  • 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 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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $580, price is now $274 per person
$274
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
the size of the room and all the extra fees at the hotel were not worth the cost

Reviewed on Jan 10, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,133, price is now $522 per person
$522
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $701, price is now $341 per person
$341
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Everyone on staff front desk to cleaning staff was wonderful to interact with. The hotel was clean and pleasant. The location was great for local food stops and also very walkable to many tourist destinations. The trains were very convenient also. Good fitness facilities. I would stay again absolutely.

Reviewed on Jan 10, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $607, price is now $327 per person
$327
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Very clean but older, small room and bed was not comfortable-seemed like a hard box with very little give to it. Staff was friendly, walkable to everything. Bodega was really good next-door

Reviewed on Jan 10, 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $586, price is now $319 per person
$319
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Maria was amazing. She made our stay perfect. Unfortunately Breakfast was not explained to us and we were not aware it was offered.

Reviewed on Jan 10, 2026

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

Discover the most popular places to visit in Rye Brook

Duran Duran plays the Capitol Theatre in Port Chester, NY in support of their Paper Gods album. Here they perform "Rio" to close out the night. #duranlive

Capitol Theatre

Enjoy a show at Capitol Theatre, a theater with a story to tell in Port Chester. Discover the entertainment choices and shops in this family-friendly area.

Capitol Theatre

Doral Arrowwood Golf Club

Enjoy a round of golf in Rye Brook at Doral Arrowwood Golf Club. Check out the shops and top-notch restaurants in this romantic area.

Doral Arrowwood Golf Club

Clay Art Center Gallery

You can study the exhibits at Clay Art Center Gallery, a museum with a story of its own, during your travels to Port Chester. Take in the entertainment choices in this family-friendly area.

Clay Art Center Gallery

What to do in Rye Brook

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

$30
per adult
88% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
Guided Kayak Fishing Tour

Guided Kayak Fishing Tour

$564
per adult
Guided Kayak Fishing Tour
See all activities in Rye Brook

Rye Brook Hotel Deals

Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Jan 21 to Jan 22
$140 total
Jan 21 - Jan 22
Total with taxes and fees
8.4/10 Very Good! (2,585 reviews)
The room

Reviewed on Jan 7, 2026

Radio Hotel
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $128 total per night from Feb 9 to Feb 10
$128 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (1,046 reviews)
I stay here every month I come to CT--safe, great bed, great staff, reliable and not expensive--what more can you want?

Reviewed on Jan 5, 2026

EVEN Hotel Norwalk by IHG
Ly New York Hotel

Ly New York Hotel

2.5 out of 5
15-61 127th St College Point NY
Fully refundable
$79 nightly
The price is $94 total per night from Jan 12 to Jan 13
$94 total
Jan 12 - Jan 13
Total with taxes and fees
8.6/10 Excellent! (1,889 reviews)
Good Customer Service. Quick to fix any issues

Reviewed on Jan 7, 2026

Ly New York Hotel
See all 1,824 properties in Rye Brook
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 Rye Brook Vacation Packages

Rye Brook Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
9,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Rye Playland, Capitol Theatre and Legoland Discovery Center Westchester

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 Rye Brook vacation package cost?
Offering great value package deals from $274 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.

Explore a world of travel with Expedia

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