Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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.
Landing Apartments New Haven Near Dixwell
Newhallville
CA $1,489
per person
Sep 17 - Sep 20
found 8 hours ago
Roundtrip flight included
Vancouver (YVR) 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
Hyatus Luxury Residences City Crossing
The Hill
CA $1,186
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.4/10 Exceptional! (33 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!
Reviewed on Jul 24, 2026
New Haven Hotel
Downtown New Haven
CA $1,162
per person
Sep 17 - Sep 20
found 8 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
9.2/10 Wonderful! (2,266 reviews)
The front desk staff was consistently friendly and helpful. The parking situation was ideal. It was all good!
Reviewed on Aug 8, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
CA $88
CA $103 total
Sep 3 - Sep 4
includes taxes & fees
7.2/10 Good! (1,019 reviews)
"Everything was great"
Reviewed on Aug 8, 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
CA $137
CA $157 total
Aug 10 - Aug 11
includes taxes & fees
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Fully refundableReserve now, pay when you stay
CA $148
CA $170 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (2,766 reviews)
"I had a really nice stay at the Hyatt in Uncasville. The hotel was clean, the staff was welcoming, and parking was super easy. I ended up in a spacious, handicap accessible room, which turned out great. The pool was a fantastic bonus, especially on a rainy day. I felt comfortable and safe as a solo ..."
Reviewed on Aug 8, 2026
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.
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.
Norma Terris Theater
You can enjoy a show at Norma Terris Theater on your trip to Chester. While you're in the area, stroll along the beautiful beaches.
Frequently asked questions
How much does a Chester vacation package cost?
You'll find cheap prices from CA $606 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?
- 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.
- 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.
- 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.
- 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.
