Chester Vacation Packages

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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.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

2 out of 5
Price was CA $955, price is now CA $881 per person
CA $881
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
7/10 Good! (1,005 reviews)
Close to Mohegan Sun which was the reason for our visit. For the most part it was decently clean. Front desk staff was friendly. Parking was easy. Very convenient and decently priced.

Reviewed on Aug. 28, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was CA $2,382, price is now CA $1,863 per person
CA $1,863
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was CA $1,293, price is now CA $1,145 per person
CA $1,145
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.8/10 Excellent! (1,737 reviews)
Very good for the price!

Reviewed on Aug. 27, 2025

Sleep Inn & Suites Niantic

Sleep Inn & Suites Niantic

2.5 out of 5
Price was CA $1,154, price is now CA $1,058 per person
CA $1,058
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
stayed 2 nights. no complaints. kids appreciated the pool

Reviewed on Aug. 26, 2025

The Niantic Inn

The Niantic Inn

2 out of 5
Price was CA $1,447, price is now CA $1,352 per person
CA $1,352
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
9.2/10 Wonderful! (103 reviews)
Superlatively clean! Fresh flowers left in room. Very quiet location and easy parking. Excellent management resolved confusion caused by Expedia. Book directly with Niantic Inn and get free beach pass! Walkable to best Niantic beaches and restaurants.

Reviewed on Aug. 20, 2025

Ready to book your vacation to Chester?

 

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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
The price is CA $98 per night from Sep 2 to Sep 3
CA $98
CA $114 total
Sep 2 - Sep 3
includes taxes & fees
6.8/10 (1,011 reviews)
"Great location, quiet & yet right near Rt 95. Clean, nice room, polite staff!!!"

Reviewed on Aug. 25, 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
The price is CA $243 per night from Sep 2 to Sep 3
CA $243
CA $314 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,973 reviews)
"Wish they had an outdoor pool"

Reviewed on Aug. 24, 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
The price is CA $164 per night from Sep 1 to Sep 2
CA $164
CA $189 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (2,541 reviews)
We would stay again
"Hotel was clean and very easy to get to. It's only a 5 minute drive to Mohegan Sun and they offer shuttle service to and from that runs every 30 minutes. The staff was very friendly and the room was spacious and clean"

Reviewed on Aug. 24, 2025

Hyatt Place Uncasville - Casino Area
See all 1,052 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.
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Frequently asked questions

How much does a Chester vacation package cost?
You'll find cheap prices from CA $881 on Expedia for your Chester break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chester costs.
What are the cheapest months to go to Chester?
Travel in the low or shoulder season and you're likely to score cheap Chester vacation packages. Remember that school vacation periods and major events and festivals can have an impact on prices, so do a little research before you go.
How many days is enough for Chester?
Chester vacations come in all shapes and sizes, but to really get a feel for this destination, we'd say 2 days is about right. With this timeframe, you can fit in headline attractions like Chester Creek Marina and Brainard Homestead State Park and seek out some lesser-known gems. Don't forget to visit cool neighbourhoods such as Deep River Centre and Essex Village either. If you're clever with your time, you can even schedule a day trip or two from Chester too.
Is it worth booking a vacation package to Chester?
From attractions such as Chester Creek Marina and Norma Terris Theatre to its excellent hiking, a Chester vacation delivers big on experiences. With so much to do and see, it's time to find out for yourself why Chester is such a good vacation destination.
How to find the best Chester package deals?
Use Expedia's filters to help you find some of the best Chester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Chester package deals in the low season. Switch up your travel dates and you may land even bigger 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 retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester trip.
How to plan a trip to Chester?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Chester.
  2. Set a budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Chester. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a more upscale getaway.
  3. Determine how many days away: Start by listing all the activities and attractions you'd like to get to in Chester. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Chester vacation package that brings all your bookings together.

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