Chester Vacations from $231

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was $289, price is now $231 per person
$231
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (786 reviews)
Clean room. Comfortable. Quiet. Bed was very comfortable.great shower pressure and hot water.

Reviewed on Mar 2, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,635, price is now $1,093 per person
$1,093
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (60 reviews)
Everything here has been excellent. I am a travel nurse and they have really helped to make my trip here the best.

Reviewed on Feb 27, 2026

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $1,817, price is now $1,318 per person
$1,318
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The place could have been a little cleaner I found hair in the bed and crumbs and dirt in the couch and under it as well the walls were stained and the carpet was stained in the bedroom it definitely was a big difference from the first time I stayed there

Reviewed on Feb 16, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,175, price is now $865 per person
$865
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Loved the location and the room!

Reviewed on Feb 23, 2026

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Save 100% on your flight
Price was $553, price is now $421 per person
$421
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
Everything was ok. People were nice. Clean room. Comfortable. Didnt have time to use the pool, but it looked nice. Breakfast was good.

Reviewed on Mar 1, 2026

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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

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
$93 nightly
The price is $107 total per night from Mar 23 to Mar 24
$107 total
Mar 23 - Mar 24
Total with taxes and fees
9.2/10 Wonderful! (2,655 reviews)
We had a great stay. Staff was very friendly

Reviewed on Mar 3, 2026

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
$221 nightly
The price is $250 total per night from Mar 29 to Mar 30
$250 total
Mar 29 - Mar 30
Total with taxes and fees
9.2/10 Wonderful! (2,053 reviews)
Had a fantastic time! My girlfriend and I will be back there for sure!!

Reviewed on Mar 2, 2026

Mohegan Sun
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd Norwich CT
Fully refundable
$97 nightly
The price is $112 total per night from Mar 15 to Mar 16
$112 total
Mar 15 - Mar 16
Total with taxes and fees
7.6/10 Good! (1,012 reviews)
We had to wait for our PAID room. The room was not cleaned nor stocked with anything. Very poor service!

Reviewed on Mar 3, 2026

Holiday Inn Norwich by IHG
See all 1,070 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

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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from $231 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.

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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.