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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Very positive experience. Staff all went above and beyond to ensure a relaxing comfortable stay. The facility was clean along with nice quiet clean rooms. 5 stars.

Reviewed on Jul. 31, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Pillows are horrible.

Reviewed on Aug. 9, 2025

Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden

3 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
9.4/10 Exceptional! (371 reviews)
It’s always pleasant when I stay here.

Reviewed on Jul. 8, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
8.4/10 Very Good! (1,011 reviews)
The staff were very friendly and helpful including when we had to unexpectedly add another night onto our trip. Conveniently located near Yale.

Reviewed on Aug. 8, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Scenic design of property and great location

Reviewed on Aug. 8, 2025

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Chester Hotel Deals

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 $176 per night from Aug 27 to Aug 28
CA $176
CA $203 total
Aug 27 - Aug 28
includes taxes & fees
9/10 Wonderful! (2,508 reviews)
"Housekeeping staff was easy to find but not intrusive. Check in and check out went fine staff was very pleasant and professional. My room was very clean and I took full advance of the breakfast, pool, and casino shuttle. This was my first time at this hotel but I had a good time."

Reviewed on Aug. 9, 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 CA $246 per night from Sep 2 to Sep 3
CA $246
CA $318 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,949 reviews)
"Such a well-run establishment. From check-in to casual restaurants to high end dining, it's just so customer friendly."

Reviewed on Aug. 6, 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 CA $128 per night from Aug 18 to Aug 19
CA $128
CA $147 total
Aug 18 - Aug 19
includes taxes & fees
7.4/10 Good! (1,003 reviews)
"Friendly staff"

Reviewed on Aug. 7, 2025

Holiday Inn Norwich by IHG
See all 1,061 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.
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $361 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.