Chester Vacations from $410

Book a Hotel + Flight or Car together to unlock savings

Photo by Annette Babek

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to $1,045 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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Higganum House B&B

Higganum House B&B

3 out of 5
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
No reviews
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Sep 19 - Sep 22
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (16 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Mayflower Inn & Spa, Auberge Resorts Collection

Mayflower Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (53 reviews)
Incredible place - will definitely return.

Reviewed on Aug 19, 2024

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Save 100% on your flight
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
We have visited Saybrook Point Resort several times and it is consistent in providing an excellent customer experience.

Reviewed on Jun 29, 2025

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.6/10 Exceptional! (50 reviews)
It was a great place. Highly recommend!

Reviewed on Jun 11, 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

Mohegan Sun
Mohegan Sun
4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $277 total per night from Jul 7 to Jul 8
$277 total
Jul 7 - Jul 8
Total includes taxes and fees
9/10 Wonderful! (1,930 reviews)
"great"

Reviewed on Jun 29, 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
$115 nightly
The price is $132 total per night from Jul 1 to Jul 2
$132 total
Jul 1 - Jul 2
Total includes taxes and fees
9/10 Wonderful! (2,441 reviews)
"All staff were very curious and accommodating. Break was very good and many options"

Reviewed on Jun 28, 2025

Hyatt Place Uncasville - Casino Area
Red Roof Inn Meriden
Red Roof Inn Meriden
2 out of 5
10 Bee St, Meriden, CT
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $114 total per night from Jul 1 to Jul 2
$114 total
Jul 1 - Jul 2
Total includes taxes and fees
7.4/10 Good! (1,004 reviews)
"Great staff and cleanliness."

Reviewed on Jun 26, 2025

Red Roof Inn Meriden
See all 1,064 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 $410 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.