Chester Vacations from $257

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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.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $329, price is now $257 per person
$257
per person
Jan 16 - Jan 18
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
17.2/10 Exceptional! (581 reviews)
A awesome place to stay whether just traveling through or staying in the area. Easy on and off the Interstate with lots of parking. A great staff from front desk to breakfast servers. Everyone made us feel at home. The rooms are spacious and feels like you are home not a hotel/motel/suite. Will definitely stay here again in the near future and recommend anyone traveling through to stop in and stay the night.

Reviewed on Nov 17, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,330, price is now $909 per person
$909
per person
Jan 2 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
No reviews
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $779, price is now $554 per person
$554
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
18/10 Exceptional! (1,874 reviews)
Great location to restaurants and bars, room was clean, easy access to parking for fee

Reviewed on Nov 24, 2025

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $681, price is now $523 per person
$523
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
16.4/10 Exceptional! (1,002 reviews)
From day one had a good experience. Everything was explained to me in detail and felt very comfortable. From the room and all. Super clean and comfortable. Personally I have no complaints at all. Thank you

Reviewed on Nov 23, 2025

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
Price was $369, price is now $295 per person
$295
per person
Feb 13 - Feb 16
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
16.4/10 Exceptional! (656 reviews)
Clean, spacious room. Excellent service. Good breakfast

Reviewed on Nov 19, 2025

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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

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 29 to Nov 30
$85 total
Nov 29 - Nov 30
Total with taxes and fees
7/10 Good! (1,004 reviews)
Food was decent; bathroom needs better cleaning. Chinthsoo and Glory were very nice.

Reviewed on Nov 20, 2025

Motel 6 New Haven - Branford, CT
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
$148 nightly
The price is $166 total per night from Dec 25 to Dec 26
$166 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (2,041 reviews)
!

Reviewed on Nov 20, 2025

Mohegan Sun
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
1954 Norwich New London Tpke Montville CT
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $77 total per night from Dec 1 to Dec 2
$77 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (1,835 reviews)
From start to finish, a good experience. Arrived early and was able to get a room and had no problem. Good experience and great people

Reviewed on Nov 19, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area
See all 1,043 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 $257 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.