Chester Vacations from AED3,963

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Newburgh (SWF)
8.4/10 Very Good! (1,003 reviews)
Upon arrival lady clerk was very dry, not a smile not a hello how are u, nothing. Was disappointed to find out that there was no indoor pool as described in the pictures. It was the reason we picked this place. The breakfast was the worst. Its a brown bag at reception with a banana muffin and granola bar. For the rates they are charging it would have been nice to have a bagel or waffles.

Reviewed on 16 April 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Newburgh (SWF)
8.2/10 Very Good! (619 reviews)
It felt clean, fresh, & safe. The room was amazing. I enjoyed my first stay; will definitely return.

Reviewed on 15 April 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Newburgh (SWF)
9.4/10 Exceptional! (986 reviews)
Loved our stay! Definitely recommend, room was very clean and spacious, did not count on having a whole fridge and stove top but great if staying long and want to make and store your own food, towels always available at the pool. Staff was very friendly! Will be staying again

Reviewed on 15 April 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to Newburgh (SWF)
9.2/10 Wonderful! (862 reviews)
We had a pleasant stay ..

Reviewed on 12 April 2025

Find the Best Chester Vacation Packages

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
The price is AED 540 per night from Apr 27 to Apr 28
AED 540
AED 611 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (1,000 reviews)
"I only stayed for the night but the front desk was nice and quick. Area is very quiet and peaceful."

Reviewed on 11 April 2025

Holiday Inn Express Hotel & Suites Chester by IHG
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
Fully refundableReserve now, pay when you stay
The price is AED 613 per night from Apr 23 to Apr 24
AED 613
AED 694 total
includes taxes & fees
23 Apr - 24 Apr
8.2/10 Very Good! (1,002 reviews)
Decent
"Exactly what I needed! Great view, cool breeze, and quiet! Staff were friendly, rooms were comfortable. The food at the restaurant is just okay."

Reviewed on 17 April 2025

Overlook Lodge at Bear Mountain
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is AED 465 per night from May 1 to May 2
AED 465
AED 550 total
includes taxes & fees
1 May - 2 May
9.2/10 Wonderful! (673 reviews)
"The best part about our stay was the staff. We were warmly greet by Anthony who took care of us immediately, provided information about the hotel's amenities, and local restaurants and shopping. The morning staff also eent above and beyond to ensure we had an amazing stay. Checking out with Rachel ..."

Reviewed on 15 April 2025

La Quinta Inn & Suites by Wyndham Middletown
See all 982 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.

Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination from AED3,963 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?
You can typically find lower prices and better availability in January, February and March. Browse our cheap Chester vacation packages and you could land some excellent off-season deals.
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.
How to plan a trip to Chester?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the activities available will also help you decide when to vacation in Chester.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Chester.
  3. Decide how many days away: Start by making a list of all the sights and activities you’d like to experience in Chester. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chester vacation package.

Discover the most popular places to visit in Chester

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

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