Chester Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Chester

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$311 per night from 25 Nov to 26 Nov
S$311
includes taxes & fees
25 Nov - 26 Nov
9/10 Wonderful! (1,663 reviews)
"Mohegan Sun, great getaway adventure"

Reviewed on 20 Nov,2024

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$163 per night from 9 Dec to 10 Dec
S$163
includes taxes & fees
9 Dec - 10 Dec
9/10 Wonderful! (2,207 reviews)
"The elevator areas are looking quite neat up and old."

Reviewed on 20 Nov,2024

Hyatt Place Uncasville - Casino Area
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$109 per night from 1 Dec to 2 Dec
S$109
includes taxes & fees
1 Dec - 2 Dec
6.6/10 (1,003 reviews)
"Excellent service"

Reviewed on 19 Nov,2024

Motel 6 New Haven - Branford, CT
See all 1,015 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?
Our Chester holiday packages, which start from as low as , are the perfect way to save loads of cash. Pick and choose your preferred hotels, flights and rental car to create a customized itinerary.
How do I get a cheap travel package to Chester?
Combine your bookings with Expedia to save big on your next getaway. With more than 550 air carriers and 1,000,000 properties across the globe, your Chester holiday package can be customized exactly to suit your budget. With all that extra cash, why not throw in one or two exciting tours and activities? It’s an easy way to unlock even more bargains. The holiday you’ve always dreamed of in Chester is much closer than you thought!
Where should I stay in Chester?
With fascinating attractions such as Chester Creek Marina and Norma Terris Theatre in this neighbourhood, try to find a hotel near either of them. Connecticut Valley Railroad State Park Trail is another Chester hot spot that people flock to.
What are the top hotels in Chester?
Many travellers choose to stay at Stunning Artisan Waterfall Escape - Walk To Downtown in Chester Centre. If it’s your first time in Chester, you’ll feel right at home here.
How far in advance should I book my Chester holiday?
Reward yourself with the widest variety and the cheapest prices by booking your trip to Chester early. Air carriers typically sell flights around 12 months in advance, so reserve your spot as soon as you can. That said, Expedia is dedicated to giving you the best deals around, so it’s always a good time to book your dream holiday!
What does an Expedia Chester travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply mix and match your favourite bundle and get access to great discounts. Once you’ve made your booking, add on a couple of sightseeing tours and watch your savings grow. When it comes to creating your Chester trip, you’re in charge!
What should I know before booking a Chester travel package?
You’ll land big savings when you bundle your hotels, flights and rental cars into a package. Plus, booking everything in one spot will make your trip planning easier. So why waste time or money? Whether you’re organising a fancy romantic getaway or a low-cost family road trip, take a look at our package deals today.
Can I choose my airline with a Chester Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Chester holiday package?
Because we know life can be unpredictable, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change it for no charge. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.

* 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.