Chester Holidays

Photo by Annette Babek

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Top hotels in Chester

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is S$106 per night from 31 Aug to 1 Sept
S$106
31 Aug - 1 Sept
includes taxes & fees
6.8/10 (1,001 reviews)
"I like that it is close to a lot of good places to eat."

Reviewed on 21 Aug, 2025

Motel 6 New Haven - Branford, CT
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Fully refundableReserve now, pay when you stay
The price is S$281 per night from 2 Sept to 3 Sept
S$281
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,964 reviews)
"Watched the FEVER win in the Arena. Had a great dinner at Tuscany. Had a great time in the casino. Rooms were very nice."

Reviewed on 22 Aug, 2025

Mohegan Sun
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich, New London Turnpike, Montville, CT
Fully refundableReserve now, pay when you stay
The price is S$187 per night from 28 Aug to 29 Aug
S$187
28 Aug - 29 Aug
includes taxes & fees
9/10 Wonderful! (2,537 reviews)
"Spider webs by floor near window and air conditioner. Pool was closed. Requested room first floor, close to lobby. (Walking too far, standing too long was a challenge) was given first floor but still had to walk all the way to far corner away from lobby."

Reviewed on 23 Aug, 2025

Hyatt Place Uncasville - Casino Area
See all 1,052 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Chester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chester?
The off-season is the best time to head to Chester if you're trying to save. Another tip for scoring cheap Chester holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Chester?
The ideal length for your Chester holiday depends on what you'd like to see. Typically, a few days to a week will give you time to go to all the main sights and discover some hidden treasures along the way.
Is it worth booking a holiday package to Chester?
Boasting a host of highlights starting with its excellent hiking, Chester is a good holiday destination. Whether you'd like to visit sights such as Chester Creek Marina and Norma Terris Theatre or take the road less traveled, you'll find loads to see and do on your Chester holiday.
How to find the best Chester package deals?
Use Expedia's filters to find some unbeatable Chester package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Chester package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester break by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Chester?
Score fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chester escape.
How to plan a trip to Chester?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Chester.
  2. Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Chester.
  3. Work out your trip length: Think about how much time you want to spend exploring Chester. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Chester holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.