Chester Vacation Packages

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Your Chester Vacation

The best way to experience this vibrant city is with a custom-made Chester vacation package. Stay in the neighborhood of Essex Village, which is good for walking, hiking and views or choose someplace else — our packages are all about you. Essex Steam Train, Goodspeed Opera House and Essex Island Marina are just some of the many sights you'll want to check out during your trip to Chester. Check out Expedia's extensive range of travel options and begin planning your perfect vacation to Chester now.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Aug 14 - Aug 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
The view was stunning and the hotel was very clean. Would definitely stay again

Reviewed on Jun. 18, 2025

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
per person
Aug 14 - Aug 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9/10 Wonderful! (1,003 reviews)
This property was convenient for flying out early in the morning. The shuttle was very helpful!

Reviewed on Jul. 7, 2025

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Aug 14 - Aug 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Very easy navigation to the hotel. Got exactly the room that I reserved, and even a little bit better. The hotel staff from front desk agent to assistant general manager to bartender to the breakfast hostess Were all incredibly friendly and warm and responsive. It felt like staying at a friend's place. Their last act upon our checkout was reflective of the service throughout our Multi-day stay: I asked if the breakfast coffee was still out and the front desk agent told me it was not but then offered to get me a cup of coffee from the kitchen, which she did right away and with a smile. It was so nice and such a kind gesture to this weary traveler, and it's the little things like that that make this a great place to stay.

Reviewed on Jul. 10, 2025

Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
per person
Aug 14 - Aug 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (256 reviews)
This hotel is older but nicely maintained. We liked using the pool and they put out wine and cheese for the guests each evening. The bed however wasn’t comfortable and difficult to sleep on. They really need to buy new mattresses.

Reviewed on Jul. 11, 2025

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Aug 14 - Aug 18
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
8.2/10 Very Good! (605 reviews)
Everything was good. No complaints. Staff was Avery friendly and helpful

Reviewed on Jul. 6, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

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 CA $97 per night from Jul 17 to Jul 18
CA $97
CA $113 total
Jul 17 - Jul 18
includes taxes & fees
6.8/10 (1,008 reviews)
"Clean, friendly, and welcoming - especially if traveling with a pet."

Reviewed on Jul. 6, 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 CA $300 per night from Jul 31 to Aug 1
CA $300
CA $379 total
Jul 31 - Aug 1
includes taxes & fees
9/10 Wonderful! (1,933 reviews)
"Area clean view from room not great but overall very nice."

Reviewed on Jul. 9, 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 CA $139 per night from Jul 16 to Jul 17
CA $139
CA $160 total
Jul 16 - Jul 17
includes taxes & fees
9/10 Wonderful! (2,439 reviews)
"Stayed 1 night for a quiet getaway and casino trip. No issues, everything from checkin to checkout went smoothly. Pool water was a little cold. Room was clean, comfortable bed and nice shower. Will stay again."

Reviewed on Jul. 10, 2025

Hyatt Place Uncasville - Casino Area
See all 1,066 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $890 on Expedia for your Chester break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
Travel in the low or shoulder season and you're likely to score cheap Chester vacation packages. Remember that school vacation periods and major events and festivals can have an impact on prices, so do a little research before you go.
How many days is enough for Chester?
Chester vacations come in all shapes and sizes, but to really get a feel for this destination, we'd say 2 days is about right. With this timeframe, you can fit in headline attractions like Chester Creek Marina and Brainard Homestead State Park and seek out some lesser-known gems. Don't forget to visit cool neighbourhoods such as Deep River Centre and Essex Village either. If you're clever with your time, you can even schedule a day trip or two from Chester too.
Is it worth booking a vacation package to Chester?
From attractions such as Chester Creek Marina and Norma Terris Theatre to its excellent hiking, a Chester vacation delivers big on experiences. With so much to do and see, it's time to find out for yourself why Chester is such a good vacation destination.
How to find the best Chester package deals?
Use Expedia's filters to help you find some of the best Chester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Chester package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester trip.
How to plan a trip to Chester?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Chester.
  2. Set a budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Chester. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Determine how many days away: Start by listing all the activities and attractions you'd like to get to in Chester. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Chester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.