Chester Vacation Packages 2026 from $1,750

Chester flight + hotel vacation packages

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

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$1,750

per person

Dec 3 - Dec 7

found 7 hours ago

Roundtrip flight included

Austin (AUS) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

Top Chester hotels deals

Hyatt Place Uncasville - Casino Area

2049 Norwich Montville CT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$127 total

Oct 29 - Oct 30

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Mohegan Sun

1 Mohegan Sun Boulevard Montville CT

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This luxury resort features a golf course, a casino, and a full-service spa. Families will appreciate the arcade/game room, onsite laundry facilities, and babysitting. Enjoy a meal in one of the 19 restaurants and free perks like valet parking and a casino shuttle.

Pool

Hot Tub

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$216 nightly

$248 total

Nov 22 - Nov 23

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

On private beach

Pool

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$82 nightly

$94 total

Nov 19 - Nov 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.

Pet friendly

Parking included

The Spa at Norwich Inn

607 W Thames St Norwich CT

Free Cancellation

Reserve now, pay when you stay

$209 nightly

$240 total

Nov 4 - Nov 5

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this historic hotel. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Pool

Hot Tub

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$64 nightly

$73 total

Nov 8 - Nov 9

Total with taxes and fees

A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.

Pet friendly

Parking included

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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.

Stay near popular Chester attractions

Norma Terris Theater

You can enjoy a show at Norma Terris Theater on your trip to Chester. While you're in the area, stroll along the beautiful beaches.

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Frequently asked questions

How much are vacation packages to Chester?

Starting at just $1,750, hotel and flight packages are a great way to make your vacation budget stretch further. Chester, here you come!

Where can I get the best vacation package deals for Chester?

No matter what you enjoy doing, Travelocity can help you find the perfect Chester package deal. All you need to do is select a combination from our 400 airlines and 1,000,000 properties across the globe.

Why should I purchase my Chester vacation bundle with Travelocity?

From our 24/7 customer support to our range of exhilarating destinations, we are committed to fulfilling your travel dreams. All you have to do is to click and book — our Price Match Guarantee will ensure you lock in the lowest price.

Will I save money on my Chester car rental if I bundle it with hotels and flights?

With a Chester vacation package, you can bundle your hotel, flight and car bookings and save a ton. If you want to explore the best of this fabulous city, why not start with Times Square? This renowned attraction is 90 mi from Chester. With a rental car, you'll be there belong long.

Which airport is best for Chester?

Many travelers fly into Bradley Intl. Airport (BDL), 40 mi north of downtown Chester. Others prefer T.F. Green Airport (PVD) (60 mi away from central Chester) or MacArthur Airport (ISP) (55 mi away from central Chester).

What is there to do in Chester?

Chester Creek Marina deserves to be on your travel schedule. After you've crossed off this popular attraction, simply roam through the streets of Chester and experience what makes this cool place tick.

Where should I stay when visiting Chester?

If you're searching for somewhere to base yourself, have a look at the Updated cottage "Beriozka" on Cedar Lake. It's the top choice for many visitors.