Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free train station pick-up. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and a shopping center shuttle.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) 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.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Free WiFi in public areas is available at this hotel. Business travelers can take advantage of the business center. Take advantage of the free self parking.

Top Chester hotels deals

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich, New London Turnpike, Montville, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
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
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard, Montville, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
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
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd, Norwich, CT
Get rates
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
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, Route 32, Montville, CT
Free Cancellation
Reserve now, pay when you stay
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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
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

3 out of 5
2255 Norwich-New London Turnpike, Montville, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free perks include continental breakfast, free self parking, and a casino shuttle.
Pool
Breakfast 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.

Popular places to visit

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.

Norma Terris Theater

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

Frequently asked questions

How much are vacation packages to Chester?
Starting at just $361, 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.

Photos of local treasures

Browse Chester vacation photos for more inspiration

Photo by Annette Babek
Photo by Annette Babek
Photo by Annette Babek
Photo by Annette Babek
Photo by Erick
Photo by Erick