Chester Vacation Packages 2025/2026 from $751

Chester flight + hotel vacation packages

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

Omni New Haven Hotel at Yale

Downtown New Haven

Save 100% on your flight

per person

Oct 9 - Oct 14

found 9 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

Save 100% on your flight

per person

Oct 9 - Oct 14

found 9 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

Madison Beach Hotel

Madison Center

Save 100% on your flight

per person

Oct 9 - Oct 14

found 9 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.

Luxury Apartments by Hyatus at Pierpont

The Hill

Save 100% on your flight

per person

Oct 9 - Oct 14

found 9 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.

Graduate by Hilton New Haven

Downtown New Haven

Save 100% on your flight

per person

Oct 9 - Oct 14

found 9 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

Top Chester hotels deals

Motel 6 New Haven - Branford, CT

320 E Main St, Branford, CT

Free Cancellation

$73 nightly

$84 total

Aug 28 - Aug 29

Total includes 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

Mohegan Sun

1 Mohegan Sun Boulevard, Montville, CT

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$231 total

Sep 2 - Sep 3

Total includes taxes and fees

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

Hyatt Place Uncasville - Casino Area

2049 Norwich, New London Turnpike, Montville, CT

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$148 total

Sep 1 - Sep 2

Total includes 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

Microtel Inn & Suites by Wyndham Uncasville Casino Area

1954 Norwich New London Tpke, Route 32, Montville, CT

$74 nightly

$85 total

Sep 7 - Sep 8

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. The front desk is staffed around-the-clock and laundry facilities are on offer.

Breakfast included

Parking included

Holiday Inn Norwich by IHG

10 Laura Blvd, Norwich, CT

Free Cancellation

$93 nightly

$107 total

Aug 24 - Aug 25

Total includes taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free casino shuttle.

Pool

Parking included

Best Western Niantic - New London/Mystic Area

265 Flanders Road, Niantic, CT

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$106 total

Sep 1 - Sep 2

Total includes taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking is offered and the front desk is staffed around-the-clock.

Pool

Pet friendly

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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.

Popular places to visit

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.

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.

Frequently asked questions

How much are vacation packages to Chester?

Starting at just $751, 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.