Chester Vacations from $208

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Your Chester Vacation

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester vacation package that's customized to you. If taking in sights is on the agenda during your trip to Chester, swing by leading attractions like LEGOLAND® New York, The Rock Sports Complex and Goshen Historic Track. Don't delay visiting this destination any longer. Your ultimate Chester vacation is a couple of clicks away with Expedia.

The Latest Chester 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
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.4/10 Good! (502 reviews)
Very cute hotel. Lobby is beautiful. Room was clean and bed was very comfortable. Bathroom was clean too. A little small though. I'd definitely stay again.

Reviewed on Aug 15, 2025

Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
6.2/10 (1,005 reviews)
I was very content. Clean room staff was amazing and very clean

Reviewed on Aug 11, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
per person
Sep 18 - Sep 21
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
9.2/10 Wonderful! (775 reviews)
Place was great have stayed here many times.

Reviewed on Jul 30, 2025

Caldwell House Bed & Breakfast

Caldwell House Bed & Breakfast

3 out of 5
Save 100% on your flight
per person
Nov 6 - Nov 10
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
9/10 Wonderful! (473 reviews)
Great place to stay. Wonderful breakfasts. Gracious and warm hospitality.

Reviewed on May 28, 2024

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
8.2/10 Very Good! (671 reviews)
The room and outdoor area was great The pool looks like it could use some updating. Had some friends visit and hung out in the garden area which was very nice as well. Fresh fruit and lemon water available daily in lobby.

Reviewed on Aug 15, 2025

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Discover the most popular places to visit in Chester

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

Chester Hotel 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
Fully refundable
$121 nightly
The price is $143 total per night from Aug 21 to Aug 22
$143 total
Aug 21 - Aug 22
Total includes taxes and fees
8.4/10 Very Good! (1,002 reviews)
"The property is nice, near to Legoland, grocery, and fast foods."

Reviewed on Aug 14, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Fully refundable
$112 nightly
The price is $130 total per night from Aug 24 to Aug 25
$130 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (1,002 reviews)
"It was very … elegant"

Reviewed on Aug 12, 2025

Crowne Plaza Suffern - Mahwah by IHG
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd, Nanuet, NY
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $122 total per night from Sep 1 to Sep 2
$122 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,007 reviews)
"It was quiet and clean. Not walking distance but not too far from restaurants"

Reviewed on Aug 11, 2025

Sonesta Simply Suites Nanuet
See all 981 properties in Chester
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.

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination from $208 on Expedia. However, how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
October, November and December are the best times to look for cheap Chester vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Chester?
Dedicate around 2 days for your Chester vacation in order to take in all that makes this destination unique. Explore popular neighborhoods, including South Blooming Grove and Walton Park. Then make a beeline for top attractions such as The Rock Sports Complex and Museum Village. With a well-organized itinerary, you'll be kept busy with room for some downtime too. Want to venture beyond Chester? Consider a day trip or two.
Is it worth booking a vacation package to Chester?
It's easy to see why a Chester vacation is on the must-do list of many travelers. Major attractions like The Rock Sports Complex are just the start of things to see and do here.
How to find the best Chester package deals?
Finding a cheap Chester package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can personalize your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
If you have your Chester travel dates finalized, book as soon as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester trip should be an escape from your daily routine, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.