Rye Brook Vacation Packages

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

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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.

Top Rye Brook Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,825, price is now CA $1,102 per person
CA $1,102
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
The best part of this hotel is the proximity and the size of the room. Hotel staff really hands-off, no amenities. Hotel very out dated and kind of dingy looking.

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,502, price is now CA $1,381 per person
CA $1,381
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,809, price is now CA $3,009 per person
CA $3,009
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $2,413, price is now CA $1,539 per person
CA $1,539
per person
Jan 13 - Jan 20
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

Ready to book your vacation to Rye Brook?

 

Choose your dates

Rye Brook Hotel Deals

Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Nov 29 to Nov 30
CA $102
CA $122 total
Nov 29 - Nov 30
includes taxes & fees
Highbridge Hotel
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Nov 9 to Nov 10
CA $200
CA $272 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very good! (2,341 reviews)
"Everything was great. The facility was simple but amazing. It had everything we needed for our trip. Would definitely be coming back to this hotel for future trips."

Reviewed on Nov 6, 2026

Radio Hotel
Four Points by Sheraton Flushing

Four Points by Sheraton Flushing

3 out of 5
33-68 Farrington St Flushing NY
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Nov 10 to Nov 11
CA $200
CA $235 total
Nov 10 - Nov 11
includes taxes & fees
Four Points by Sheraton Flushing
See all 1,748 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.
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Stay near popular Rye Brook attractions

Capitol Theatre

7.4/10 (117 reviews)
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.
See properties

What to do in Rye Brook

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $997
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Rye Brook

Frequently asked questions

How much does a Rye Brook vacation package cost?
Offering excellent value package deals from CA $1,102 on Expedia, you'll be surprised at how little a vacation to Rye Brook costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Rye Brook?
If you'd like to book a cheap Rye Brook vacation package, consider visiting in January, February and August. You'll usually find lower prices on airfares and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Rye Brook?
To fully enjoy a Rye Brook vacation, we suggest staying for 2 days. Divide your time between visiting The Westchester Mall, Westchester Country Club and other major sights, as well as exploring neighbourhoods like Harrison and Fairview. If you've got some spare time, add a tour or day trip to your Rye Brook vacation itinerary.
Is it worth booking a vacation package to Rye Brook?
Rye Brook is a good vacation destination with attractions like Capitol Theatre among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Rye Brook vacation promises fun for everyone.
How to find the best Rye Brook package deals?
Bagging a cheap Rye Brook package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Rye Brook 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 generally lower.
Is it cheaper to book a Rye Brook vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Rye Brook vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Rye Brook?
If you're considering a spur-of-the-moment Rye Brook adventure, browse 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 well in advance.
How to plan a trip to Rye Brook?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the type of activities on offer will also help you decide when to visit Rye Brook.
  2. Budget wisely: As well as the cost of your accommodations, you should factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Rye Brook.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Rye Brook. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Rye Brook vacation package.

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