Port Chester Vacations from $663
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Your Port Chester Vacation
When a city getaway is calling, answer it with a vacation package to Port Chester. The neighborhood of Downtown Stamford, which is good for history, bars and pubs and dining, makes a great base for your adventures. A trip to Port Chester is a wonderful opportunity to take in the sights. Check out well-known attractions like Capitol Theatre, Doral Arrowwood Golf Club and Clay Art Center Gallery. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Port Chester vacation plans into gear!
The Latest Port Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway
Manhattan
$663
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (3,584 reviews)
With very few hotel choices in the very upper west side, we gave this one a second chance. Typical small, dank rooms, but a nice lobby and Great staff. Our toilet was nonfunctioning, but since it was the middle of the night we dealt with it. No price break was offered.
Reviewed on Sep 19, 2026
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View all tripsStay near popular Port Chester attractions
Capitol Theatre
7.4/10 (117 reviews)
This historic venue captivates with exceptional acoustics and intimate performances from renowned artists. Arrive early to enjoy the theater's vintage architecture and pre-show ambiance in the stylish lounge areas.
Capitol Theatre - Garcia’s
After visiting Capitol Theatre - Garcia’s, make a plan to see the other sights and activities in Port Chester. Experience the area's live music and entertainment venues.
Clay Art Center Gallery
This renowned ceramic arts hub showcases exhibitions from emerging and established artists since 1957. Explore the gallery, join a Wednesday morning tour, and find unique handcrafted pieces in their retail shop.
Port Chester-Rye Brook Public Library
Enjoy an outing to Port Chester-Rye Brook Public Library during your stay in Port Chester. Amble around the area's waterfront or experience its live music.
What to do in Port Chester
Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)
$5
per adult
Port Chester Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$264 nightly
$306 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (2,412 reviews)
"I spent 2 nights there and the service and room were really great. We had booked the studio suite with 1 king bed and had a little living area. We were so pleased as we walked in, we were on the 11th floor and had a beautiful view of the city from our 3 windows. The room was clean and very spacious ..."
Reviewed on Sep 19, 2026
DoubleTree by Hilton Fort Lee - George Washington Bridge
2117 Route 4 Eastbound Fort Lee NJ
Fully refundableReserve now, pay when you stay
$130 nightly
$149 total
Oct 1 - Oct 2
Total with taxes and fees
8/10 Very Good! (1,196 reviews)
"The place was very nice and staff was great. The only problem was that the room ac would only work for about 90 minutes. I called the maintenance people, they came up and since I turned the unit off and back on it was working so they left. 90 minutes later it was off and room was 78 degrees. This ..."
Reviewed on Sep 19, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$176 nightly
$201 total
Sep 27 - Sep 28
Total with taxes and fees
8.2/10 Very Good! (1,304 reviews)
"You need a Sherpa to navigate! Stairs to no where.... up down around.... out door lighting negligible. Treacherous steps and paths! We are just too old! But! What a lovely place for a big reunion or celebration! The room was large and comfortable! We came late in the evening, staff was minimal.... ..."
Reviewed on Sep 19, 2026
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 Port Chester Vacation Packages
Port Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | John F. Kennedy Intl. Airport (JFK) |
Population | 29,600 |
Top Sights | Capitol Theatre, Doral Arrowwood Golf Club and Clay Art Center Gallery |
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Frequently asked questions
How much does a Port Chester vacation package cost?
Offering excellent value package deals from $663 on Expedia, you'll be thrilled with how little a vacation to Port Chester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Port Chester?
If you'd like to book a cheap Port Chester vacation package, consider planning a trip in February, September and October. You'll typically find better prices on hotels and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Port Chester?
The ideal length of your Port Chester vacation depends on what you'd like to do. Generally, a few days to a week will give you enough time to go to all the major attractions and discover some hidden gems along the way.
Is it worth booking a vacation package to Port Chester?
It's no wonder a Port Chester vacation is on the must-do list of many travelers. Top attractions like Capitol Theatre are just the start of things to keep you busy here.
How to find the best Port Chester package deals?
Finding a cheap Port Chester package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Port Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Port Chester vacation as a package?
You can enjoy significant savings on your next Port Chester break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Port Chester?
Score incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Port Chester break.
Does Expedia offer Book Now, Pay Later Port Chester vacation packages?
Your Port Chester getaway is meant to be an escape from your daily routine, not a source of money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
