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.
Newburgh Inn

Newburgh Inn

2 out of 5
Price was $214, price is now $193 per person
$193
per person
Jan 27 - Jan 29
found 1 hour ago
Roundtrip flight included
Houston (IAH) 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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $231, price is now $193 per person
$193
per person
Jan 27 - Jan 29
found 1 hour ago
Roundtrip flight included
Houston (IAH) 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.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $228, price is now $194 per person
$194
per person
Jan 27 - Jan 29
found 1 hour ago
Roundtrip flight included
Houston (IAH) to Newburgh (SWF)
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.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $516, price is now $446 per person
$446
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Houston (IAH) 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.
Caldwell House Bed & Breakfast

Caldwell House Bed & Breakfast

3 out of 5
Price was $438, price is now $411 per person
$411
per person
Feb 13 - Feb 15
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Free full breakfast is served. A garden, a lobby fireplace, and a library are also on offer.

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
$95 nightly
The price is $112 total per night
$112 total
Jan 1 - Jan 2, 2026
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
$98 nightly
The price is $114 total per night
$114 total
Jan 4 - Jan 5, 2026
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
$102 nightly
The price is $119 total per night
$119 total
Dec 22 - Dec 23
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
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Free Cancellation
$114 nightly
The price is $133 total per night
$133 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
Pet friendly
Parking 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
$114 nightly
The price is $131 total per night
$131 total
Jan 1 - Jan 2, 2026
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
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
$98 nightly
The price is $120 total per night
$120 total
Jan 11 - Jan 12, 2026
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
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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

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

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

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 $193. 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

Browse Chester vacation photos for more inspiration