Chester Vacations from $332

Book a Hotel + Flight or Car together to unlock savings

Photo by Erick

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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.

The Latest Chester vacation packages

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
Price was $379, price is now $332 per person
$332
per person
Jan 16 - Jan 18
found 18 hours ago
Roundtrip flight included
Denver (DEN) to New Haven (HVN)
8.2/10 Very Good! (1,009 reviews)
Clean, comfortable, and affordable. The staff were incredibly nice. Upon entering the room, we quickly realized the sink wouldn’t drain. We told them on our way out to activities and it was fixed by the time we got back. They answered all our questions from things about the pool, to the laundry facility. The housekeeping ladies did a great job and were kind as well!

Reviewed on Nov 5, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $468, price is now $371 per person
$371
per person
Jan 16 - Jan 18
found 18 hours ago
Roundtrip flight included
Denver (DEN) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
Rooms and hotel were nice, but overall the place fell a little short of expectations. Negative points during our stay were the broken wi-fi, the TV's on-screen guide was reminiscent of the early 1990's with a slowly scrolling screen that shows a few channels at a time, and the instant "stir grounds into hot water" coffee was awful. Jaimee at the front desk was the best part of our stay. She was pleasant, friendly, very helpful, and she went out of her way to make us feel welcome and comfortable.

Reviewed on Nov 10, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $478, price is now $385 per person
$385
per person
Dec 17 - Dec 21
found 10 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.6/10 Excellent! (575 reviews)
Great place and great view

Reviewed on Oct 26, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $405, price is now $351 per person
$351
per person
Jan 16 - Jan 18
found 18 hours ago
Roundtrip flight included
Denver (DEN) to New Haven (HVN)
8.8/10 Excellent! (934 reviews)
Not having breakfast here

Reviewed on Nov 7, 2025

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $441, price is now $385 per person
$385
per person
Jan 16 - Jan 18
found 18 hours ago
Roundtrip flight included
Denver (DEN) to New Haven (HVN)
9/10 Wonderful! (1,842 reviews)
Always happy to be there! Great staff and convenient location, perfect for a short stay on campus.

Reviewed on Nov 8, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

Discover the most popular places to visit in Chester

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.

Chester Creek Marina

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
$74 nightly
The price is $85 total per night from Nov 19 to Nov 20
$85 total
Nov 19 - Nov 20
Total with taxes and fees
7/10 Good! (1,004 reviews)
Room clean and comfortable. No fridge but ice available and microwave available for guest use. Staff friendly. Nice pizza restaurant attached to hotel.

Reviewed on Oct 28, 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
$174 nightly
The price is $196 total per night from Nov 25 to Nov 26
$196 total
Nov 25 - Nov 26
Total with taxes and fees
9/10 Wonderful! (2,032 reviews)
Everyone in guest services was very kind and helpful. The room was beautiful and clean. I would definitely stay here again. No complaints!!

Reviewed on Nov 8, 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
$106 nightly
The price is $122 total per night from Nov 16 to Nov 17
$122 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (2,583 reviews)
Room was ok

Reviewed on Nov 12, 2025

Hyatt Place Uncasville - Casino Area
See all 1,044 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
1,550
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from $332 on Expedia, you'll be thrilled with how little a vacation to Chester costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chester?
If you're looking to score a cheap Chester vacation package, consider planning a trip in December, January and February. You'll typically find better rates on flights and accommodations during these months — perfect for budget-conscious travelers.
How many days is enough for Chester?
With a well-organized itinerary, you can easily hit the main Chester sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Chester vacation for longer.
Is it worth booking a vacation package to Chester?
Known for its hiking and home to popular attractions like Chester Creek Marina, a Chester vacation is sure to leave an impression. Another top sight to check out? Don't miss Norma Terris Theater.
How to find the best Chester package deals?
Use Expedia's filters to find some unbeatable Chester package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Chester package deals in the low season. Play around with your travel dates and you may land even better 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 break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
Score fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chester escape.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester getaway is meant to be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

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