Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Save 100% on your flight
per person
Aug 8 - Aug 14
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Jul 8 - Jul 12
found 9 hours 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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Jul 27 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
A nightclub and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a lobby fireplace, and a computer station 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
Get rates
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
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Free Cancellation
Reserve now, pay when you stay
Get rates
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 hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Free Cancellation
Reserve now, pay when you stay
Get rates
A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.
Pool
Spa
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
Get rates
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
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Parking included
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
Get rates
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
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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

Goosepond Mountain State Park

You can take time to visit Goosepond Mountain State Park during your travels to Chester. Visit the shops in this family-friendly area, or simply enjoy its restaurants.

Goosepond Mountain State Park

Frequently asked questions

How much are vacation packages to Chester?
Travelocity provides package deals to Chester, including hotels and flights, from an impressive $300. 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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