Chester Holidays from £820

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Your Chester Holiday

The exciting city of Chester is calling. Discover its hot spots and hidden treasures with a Chester holiday package that's customised 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 holiday is a couple of clicks away with Expedia.

The Latest Chester Holiday Deals

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
4 Aug - 8 Aug
found 19 hours ago
Return direct flight included
Edinburgh (EDI) to Newburgh (SWF)
8.4/10 Very Good! (1,005 reviews)
Exceeded expectations!

Reviewed on 17 Jun 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
31 Aug - 7 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Newburgh (SWF)
7.6/10 Good! (432 reviews)
My room was very clean the only thing I didn't like was the AC didn't work in the room and it was hot that weekend. Also it's been a week an I still don't have my deposit back😞

Reviewed on 13 Jun 2025

Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
per person
4 Sept - 8 Sept
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Newburgh (SWF)
9.6/10 Exceptional! (51 reviews)
Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch

Reviewed on 15 May 2025

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
3,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Brotherhood Winery, Warwick Valley Winery and Distillery and Mount Peter Ski Area

Our pick of the best 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
Stay at this business-friendly hotel in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.4/10 Very Good! (1,002 reviews)
Okay stay.
"It was an okay stay. The was a time where my keycards stopped working before we left. The breakfast was good but the first morning, there were some front desk employees kind of holding up a line in getting their breakfast before customers could get theirs. And the biscuits were not cooked all the ..."

Reviewed on 16 Jun 2025

Holiday Inn Express Hotel & Suites Chester by IHG
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,019 reviews)
"Hotel was good, fairly clean. Older property. Simple room with plenty of space for 2 people."

Reviewed on 15 Jun 2025

HYATT house Fishkill/Poughkeepsie
Extended Stay America Suites Ramsey Upper Saddle River
Extended Stay America Suites Ramsey Upper Saddle River
2.5 out of 5
112 State Hwy. 17, Ramsey, NJ
Stay at this business-friendly hotel in Ramsey. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
6.6/10 (972 reviews)
"This extended stay in New Jersey had construction on either side, so there was a lot of construction noise and I think most of the clients are people coming in for work to New Jersey or in and out of there we were there as a pitstop on the way to some somewhere else. It is a very basic room there’s ..."

Reviewed on 14 Jun 2025

Extended Stay America Suites Ramsey Upper Saddle River
See all 988 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Chester travel package cost?
Discover the best of Chester from just £820. We offer a great selection of rental cars, hotels and flights to suit every budget. You can score even better deals when you add some tours or activities to your travel package.
If I'm not able to travel, can I cancel my Chester travel package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can cancel or change your Chester travel package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.
How do I get a cheap travel package to Chester?
If you love amazing deals, bundle your bookings into a Chester travel package. Whether you're looking for hotels, flights, tours or rental cars, you can browse and book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotels throughout the world to choose from. Fly with who you want, stay wherever you like and save a bundle --- now that's the ideal escape!
Does Expedia offer Book Now, Pay Later Chester holidays?
We do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits best during the checkout process and take away the stress of budgeting for your next trip. Remember to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:
  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all types of budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Hitting the "book now" button is easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.

Where should I stay in Chester?
With fascinating attractions like LEGOLAND® New York and Castle Fun Centre in this neighbourhood, try to find a hotel near them. Museum Village is another sight in Chester that draws the crowds.
What are the top hotels in Chester?
Get your trip off to an excellent start by locking in a room at Super 8 by Wyndham Newburgh/West Point Near Stewart Airport. It's one of most popular hotels in Chester. Another option is Hampton Inn Harriman Woodbury.
How far in advance should I book my Chester holiday?
Savvy travellers book early. Airlines usually advertise flights around a year ahead of departure, and this is a fantastic opportunity to score some rock-bottom prices. Boss just told you to use up all your holiday days next week? That's fine too --- Expedia are never short of fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Chester travel package include?
Flights, rental cars and hotels, or any combination of the three --- the choice is all yours! Whether you're exploring Chester on a family road trip or travelling with your friends, there's a package to suit your style and budget. Once you've made your booking, why not add on one or two tours or activities?
What should I know before booking a Chester travel package?
When you book your flights, hotels and car rentals together, you'll pick up incredible discounts. Whether you're planning an island getaway in a villa or prefer to stay in a luxurious city hotel, Expedia will make it happen for less.
Can I choose my airline with a Chester Expedia travel package?
With a travel package, you're the boss. Whether you're hoping to fly to Chester in business or coach, simply pick from the available airline options. Expedia has access to more than 550 airline partners across the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.