Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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 out of 5
Price was $274, price is now $251 per person
$251
per person
May 8 - May 10
found 1 day ago
Roundtrip 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.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $398, price is now $309 per person
$309
per person
May 8 - May 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $534, price is now $496 per person
$496
per person
Jun 7 - Jun 11
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

3 out of 5
Price was $523, price is now $502 per person
$502
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
Price was $427, price is now $427 per person
$427
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Free self parking, a computer station, and luggage storage are also offered.

Top Chester hotels deals

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Free Cancellation
$110 nightly
The price is $130 total per night
$130 total
Apr 12 - Apr 13
Total with taxes and fees
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.
Pool
Breakfast included
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
$110 nightly
The price is $128 total per night
$128 total
Apr 19 - Apr 20
Total with taxes and fees
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.
Pool
Hot Tub
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
$97 nightly
The price is $113 total per night
$113 total
Apr 12 - Apr 13
Total with taxes and fees
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.
Pet friendly
Parking included
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Free Cancellation
$106 nightly
The price is $125 total per night
$125 total
Apr 14 - Apr 15
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr Central Valley NY
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $140 total per night
$140 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free train station pick-up. Free perks include on-the-go breakfast, free self parking, and a shopping center shuttle.
Pool
Breakfast included
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

2.5 out of 5
290 Rt 17s Mahwah NJ
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $121 total per night
$121 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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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

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

Castle Fun Center

4/5(7 reviews)

You can take time to visit Castle Fun Center during your travels to Chester. While you're in the area, find time to visit its shops.

Castle Fun Center

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 provides package deals to Chester, including hotels and flights, from an impressive $251. With the cash you save, you could purchase some cool tours or maybe also tack on some extra days to your exciting adventure.
How long should my Chester vacation be?
Around 2 nights is what many visitors book for their Chester trip. That's a handy guide, but there's loads more to explore if you allow yourself a couple of extra days.
Where can I get the best vacation package deals for Chester?
For an excellent package deal to Chester, book with Travelocity. Take your pick of 400 airlines and 1,000,000 properties across the globe to create your dream escape — it's really that easy.
Why should I book my Chester vacation package via Travelocity?
Whether you're planning a weeks-long vacation or a last-minute weekend escape, we have loads of amazing destinations to choose from at an affordable price. What's more, we provide 24/7 assistance, excellent service and a Price Match Guarantee. Save yourself the effort and time and secure your dream vacation now.
Can I save money on my Chester car rental if I bundle it with a hotel or flight?
With a Chester vacation package, you can combine your flight, hotel and car bookings and save tons. If you can't wait to uncover the best of this wonderful region, why not start with Times Square? This well-known attraction is 45 mi from Chester. With your own rental car, you'll be there in no time.
Which airport is best for Chester?
John F. Kennedy Intl. Airport (JFK) is popular. You'll find it around 55 mi southeast of Chester. Other options worth considering are Liberty Intl. Airport (EWR) (45 mi away from central Chester) and LaGuardia Airport (LGA) (45 mi away from central Chester).
What is there to do in Chester?
Chester is brimming with sights to explore, like The Rock Sports Complex and Museum Village. These well-known attractions are at the top of most travelers' itineraries.
Where should I stay when visiting Chester?
The Holiday Inn Express Hotel & Suites Chester, an IHG Hotel is the number one choice of many visitors. Book now before it's too late.

Photos of local treasures

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Black dirt region farm Chester New York