Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 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

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.
Clarion Hotel & Suites Hamden - New Haven

Clarion Hotel & Suites Hamden - New Haven

2.5 out of 5
per person
Jul. 1 - Jul. 4
found 1 day ago
Roundtrip non-stop flight included
Victoria (YYJ) to New Haven (HVN)
6.6/10 (1,002 reviews)
Good location. Reasonable price

Reviewed on Mar. 29, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
per person
Jul. 1 - Jul. 4
found 1 day ago
Roundtrip non-stop flight included
Victoria (YYJ) to New Haven (HVN)
9.4/10 Exceptional! (13 reviews)
My husband and I both loved this property and it’s convenient location; so much that we even discussed purchasing one of the apartments as a condo! We ran a bit over checkout and the property manager was very communicative and accommodating. A wonderfully quaint, quiet, and walkable location with great food options in close proximity to prominent institutions. Definitely will stay again.

Reviewed on Apr. 14, 2025

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
per person
Jul. 1 - Jul. 4
found 1 day ago
Roundtrip non-stop flight included
Victoria (YYJ) to New Haven (HVN)
9/10 Wonderful! (78 reviews)
Small beach. No staff regularly on duty. Otherwise, cute room with relaxed beach vibe. Coffee room with a view was a nice touch.

Reviewed on Apr. 30, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
per person
Jul. 1 - Jul. 4
found 1 day ago
Roundtrip non-stop flight included
Victoria (YYJ) to New Haven (HVN)
8.6/10 Excellent! (1,005 reviews)
Property is a hidden gem because it's in an industrial area. Breakfast is good, enjoyed the heated whirlpool to relax. Staff was very welcoming.

Reviewed on Apr. 21, 2025

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
per person
Jul. 1 - Jul. 4
found 1 day ago
Roundtrip non-stop flight included
Victoria (YYJ) to New Haven (HVN)
7.8/10 Good! (1,025 reviews)
Very clean and comfortable. Generous size vanity. Extra chair in room. Wonderful breakfast. But entrance to driveway was difficult to find.

Reviewed on Apr. 28, 2025

Ready to book your vacation to Chester?

 

Choose your dates

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 $169 per night from May 8 to May 9
CA $169
CA $195 total
includes taxes & fees
May 8 - May 9
"The hotel was good and free breakfast was also provided. The receptionist staff were accompanying as well as the kitchen staff. Housekeeping staff was okay. However, I noticed that they did not change the bed sheet and pillow cases. On that day, my 9 year old son did not want to leave the room. One ..."

Reviewed on Apr. 27, 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 $261 per night from May 22 to May 23
CA $261
CA $335 total
includes taxes & fees
May 22 - May 23
9/10 Wonderful! (1,842 reviews)
"Wonderful place great people made our day me love It here"

Reviewed on Apr. 30, 2025

Mohegan Sun
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from May 7 to May 8
CA $130
CA $149 total
includes taxes & fees
May 7 - May 8
7.4/10 Good! (1,007 reviews)
"Excellent customer service"

Reviewed on Apr. 22, 2025

Clarion Inn
See all 1,041 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 $647 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.