Chester Holidays

Photo by Annette Babek

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Top Flight + Hotel Deals in Chester

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
15 Oct - 19 Oct
found 21 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
7/10 Good! (888 reviews)
The pool wasn’t open, the room needed to be updated, bathroom outlet didn’t work, tv was static, I wouldn’t stay again.

Reviewed on 27 Jul 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
15 Oct - 19 Oct
found 21 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
I love this property. But, very disappointed in the pool and lack of variety of food

Reviewed on 9 Aug 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
15 Oct - 19 Oct
found 21 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

The Captain Stannard

The Captain Stannard

3 out of 5
Westbrook Center
per person
15 Oct - 19 Oct
found 21 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.6/10 Exceptional! (237 reviews)
This is as nice a place as can be. 10 stars all the way from checkin to check out. Do not hesitate to book here

Reviewed on 25 Jul 2025

The Niantic Inn

The Niantic Inn

2 out of 5
per person
15 Oct - 19 Oct
found 21 hours ago
Return direct flight included
London (LHR) to New Haven (HVN)
9.2/10 Wonderful! (103 reviews)
Everything was great .Location is perfect to shop and dine. Only issue was garbage was left in stairwells overnight

Reviewed on 2 May 2025

Top hotels in Chester

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 €126 per night from 27 Aug to 28 Aug
€126
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (2,495 reviews)
"Great clean hotel room with 3 minute drive to casino. Free breakfast was really good. Staff was great"

Reviewed on 7 Aug 2025

Hyatt Place Uncasville - Casino Area
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 €198 per night from 2 Sept to 3 Sept
€198
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,943 reviews)
"We got a room upgrade and we were SOOOOOO excited to stay in the Sugar Maple Suite!"

Reviewed on 8 Aug 2025

Mohegan Sun
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd, Norwich, CT
Fully refundable
The price is €92 per night from 18 Aug to 19 Aug
€92
18 Aug - 19 Aug
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"Friendly staff"

Reviewed on 7 Aug 2025

Holiday Inn Norwich by IHG
See all 1,059 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 from €627 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.