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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $410, price is now $315 per person
$315
per person
Dec 30 - Jan 3
found 23 hours ago
Roundtrip flight included
Chicago (ORD) 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 $699, price is now $525 per person
$525
per person
Dec 26 - Jan 2
found 1 hour ago
Roundtrip flight included
Chicago (ORD) 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.
Cottage Suites

Cottage Suites

2 out of 5
Save 100% on your flight
Price was $970, price is now $750 per person
$750
per person
Dec 26 - Jan 2
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was $826, price is now $649 per person
$649
per person
Dec 26 - Jan 2
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was $641, price is now $517 per person
$517
per person
Dec 26 - Jan 2
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

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
$123 nightly
The price is $145 total per night
$145 total
Oct 26 - Oct 27
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
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
$95 nightly
The price is $111 total per night
$111 total
Oct 26 - Oct 27
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
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night
$129 total
Oct 26 - Oct 27
Total with taxes and fees
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.
Parking included
Free WiFi
Hampton Inn Nanuet

Hampton Inn Nanuet

2.5 out of 5
260 W Route 59, Nanuet, NY
$98 nightly
The price is $109 total per night
$109 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a gym. 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.
Pool
Breakfast included
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
$104 nightly
The price is $118 total per night
$118 total
Nov 3 - Nov 4
Total with taxes and fees
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 Mahwah

DoubleTree by Hilton Mahwah

4 out of 5
180 Route 17 S, Mahwah, NJ
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $131 total per night
$131 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a restaurant, a 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.
Parking included
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

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

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 $315. 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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