Chester Vacations from $331

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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.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $473, price is now $331 per person
$331
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
It was a nice stay. I enjoyed the breakfast that we paid for. I did not enjoy paying for parking. The room was what I would expect for the price... Very nice and clean

Reviewed on Dec 13, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,603, price is now $893 per person
$893
per person
Jan 31 - Feb 3
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
Price was $410, price is now $332 per person
$332
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
7.8/10 Good! (1,003 reviews)
The staff was friendly. The room was good.

Reviewed on Dec 14, 2025

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $525, price is now $434 per person
$434
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9/10 Wonderful! (1,874 reviews)
Everything went well. My short stay was good. I particularly like the hotel's proximity to my favorite places in New Haven. Also the general cleanliness and overall pleasant atmosphere.

Reviewed on Dec 16, 2025

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $2,471, price is now $2,055 per person
$2,055
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.2/10 Wonderful! (54 reviews)
Incredible place - will definitely return.

Reviewed on Aug 19, 2024

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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

Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $219 total per night from Jan 4 to Jan 5
$219 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (2,059 reviews)
First timers, and really enjoyed it!

Reviewed on Dec 15, 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 21 to Dec 22
$77 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,849 reviews)
The room was very clean. The bed was very comfortable, on the soft side and the shower was amazing.

Reviewed on Dec 14, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area
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
$98 nightly
The price is $113 total per night from Dec 24 to Dec 25
$113 total
Dec 24 - Dec 25
Total with taxes and fees
9/10 Wonderful! (2,608 reviews)
Room was spacious and comfortable

Reviewed on Dec 16, 2025

Hyatt Place Uncasville - Casino Area
See all 1,045 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 $331 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.