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.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was CA $540, price is now CA $495 per person
CA $495
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.4/10 Very good! (834 reviews)
Good value

Reviewed on Jul 9, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,246, price is now CA $1,018 per person
CA $1,018
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,060, price is now CA $1,733 per person
CA $1,733
per person
Aug 11 - Aug 14
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was CA $911, price is now CA $841 per person
CA $841
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,084 reviews)
Grear experience at check jn . Clean hotel

Reviewed on Jul 9, 2026

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
Price was CA $541, price is now CA $504 per person
CA $504
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
6.8/10 (1,013 reviews)
Room was clean. Staff was amazing.

Reviewed on Jul 9, 2026

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Chester Hotel Deals

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Aug 5 to Aug 6
CA $163
CA $187 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (2,722 reviews)
"Nice, spacious and clean room."

Reviewed on Jul 10, 2026

Hyatt Place Uncasville - Casino Area
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is CA $121 per night from Jul 13 to Jul 14
CA $121
CA $140 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very good! (1,013 reviews)
"The room was hot, and AC barely worked."

Reviewed on Jul 10, 2026

Pier Blue Inn Old Saybrook - Essex
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jul 12 to Jul 13
CA $140
CA $161 total
Jul 12 - Jul 13
includes taxes & fees
7.4/10 Good! (1,006 reviews)
"Clean room"

Reviewed on Jul 7, 2026

Red Roof Inn Meriden
See all 1,098 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
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Stay near popular Chester attractions

Chester Creek Marina

Explore the waterfront in Chester with a trip to Chester Creek Marina. While you're in the area, stroll along the beautiful beaches.
See properties

Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $495 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.

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