Chester Vacation Packages

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Flight and hotel packages to Chester

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2.5 out of 5
per person
Jun 7 - Jun 10
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box is provided and the front desk is staffed around-the-clock.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Jun 7 - Jun 10
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. The front desk is staffed around-the-clock and laundry facilities are on offer.
Newburgh Inn

Newburgh Inn

2 out of 5
per person
Jun 7 - Jun 10
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
Free WiFi in public areas is available at this hotel. Traveling on business? Take advantage of the conference center and conference space on site. Take advantage of the free self parking.

Top Chester hotel deals

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

2.5 out of 5
2 Bryle Place, Chester, NY
Free Cancellation
The price is $112 per night
$112
per night
May 2 - May 3
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59, Nanuet, NY
Free Cancellation
Reserve now, pay when you stay
The price is $127 per night
$127
per night
May 12 - May 13
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
551 Route 211 E, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
per night
May 1 - May 2
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Pet friendly
Breakfast included
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd, Nanuet, NY
Free Cancellation
Reserve now, pay when you stay
The price is $122 per night
$122
per night
May 12 - May 13
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a 24-hour front desk and limo/town car service are also provided.
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Free Cancellation
The price is $119 per night
$119
per night
May 6 - May 7
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and free perks like buffet breakfast and free self parking.
Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

3 out of 5
140 NJ-17 South, Mahwah, NJ
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
per night
May 27 - May 28
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast available
Free WiFi
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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.

Popular places to visit in Chester

Image for The Rock Sports Complex

The Rock Sports Complex

4/5(4 reviews)

Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops.

The Rock Sports Complex
Image for Castle Fun Center

Castle Fun Center

4/5(7 reviews)

Enjoy an outing to Castle Fun Center during your stay in Chester. While you're in the area, find time to visit its shops.

Castle Fun Center
Image for Museum Village

Museum Village

5/5(1 review)

You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops.

Museum Village

Frequently asked questions

How much are vacation packages to Chester?
Travelocity offers hotel and flight packages from as low as $377. With such amazing bargains, you’ll be saying hello to Chester before you know it.
How long should my Chester vacation be?
If you need some guidance, most visitors spend around 2 nights in Chester. But to discover the true essence of this place, stay a few extra days. That way you can explore more and really experience the local culture.
Where can I get the best vacation package deals for Chester?
It’s simple — head to Travelocity. With no less than 400 airlines and 1,000,000 properties across the globe, it’s easy to craft a Chester package deal that suits your travel style.
Why should I purchase my Chester vacation package via Travelocity?
From our 24/7 customer care to our range of terrific destinations, we are committed to fulfilling your vacation dreams. All you’ll have to do is to click and book — our Price Match Guarantee will ensure you get the best price.
Can I save money on my Chester car rental if I book it with my hotel or flight?
With a Chester vacation package, you can combine your flight, hotel and car bookings and save a ton. If you can’t wait to discover the best of this impressive area, why not start with Times Square? This well-known sight is 45 mi from Chester. With your own wheels, you’ll be there in the blink of an eye.
What is the best time of year to go to Chester?
If you love wandering wisely, is an ideal time to do it. That’s when hotel rates are at their most affordable. By way of comparison, prices are highest around . January, February and March are the most popular months to stay in Chester, so brace for snaking lines at famous attractions. Want to avoid high season? You’ll find thinner crowds in October, November and December.
Which airport is best for Chester?
John F. Kennedy Intl. Airport (JFK) (55 mi away from downtown), Liberty Intl. Airport (EWR) (45 mi away from central Chester) and LaGuardia Airport (LGA) (45 mi away from central Chester) are the main options in Chester.
What is there to do in Chester?
While venturing off the beaten track can be rewarding, you shouldn’t ignore the big-name sights that make a destination famous. The Rock Sports Complex and Castle Fun Center are just two of them in Chester.
Where should I stay when visiting Chester?
If you’re looking for a place to spend your nights, consider the Holiday Inn Express Hotel & Suites Chester, an IHG Hotel. It’s the top pick for many visitors.