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
Save 100% on your flight
per person
Oct 29 - Nov 1
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Save 100% on your flight
per person
Nov 6 - Nov 9
found 16 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Oct 29 - Nov 1
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Caldwell House Bed & Breakfast

Caldwell House Bed & Breakfast

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 18 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Oct 30 - Nov 3
found 21 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

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
$127 nightly
The price is $150 total per night
$150 total
Aug 21 - Aug 22
Total includes 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
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Free Cancellation
$112 nightly
The price is $130 total per night
$130 total
Aug 24 - Aug 25
Total includes 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. Free self parking, a garden, and a snack bar/deli are also offered.
Pet friendly
Parking 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
$105 nightly
The price is $122 total per night
$122 total
Sep 1 - Sep 2
Total includes 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
$95 nightly
The price is $113 total per night
$113 total
Sep 15 - Sep 16
Total includes 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
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
$126 nightly
The price is $143 total per night
$143 total
Aug 26 - Aug 27
Total includes 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
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E, Middletown, NY
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $144 total per night
$144 total
Aug 25 - Aug 26
Total includes 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 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

Castle Fun Center

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

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

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 $189. 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