Deals on vacations and trips to Chester
Save when you book Chester package deals
Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
New Haven Hotel
Downtown New Haven
Price was $519, price is now $419 per person
$419
per person
Jun 22 - Jun 25
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Save 100% on your flight
Price was $981, price is now $634 per person
$634
per person
Jun 30 - Jul 7
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
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 and barbecue grills are also provided.
Omni New Haven Hotel at Yale
Downtown New Haven
Price was $596, price is now $458 per person
$458
per person
Jun 22 - Jun 25
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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.
Graduate by Hilton New Haven
Downtown New Haven
Price was $612, price is now $497 per person
$497
per person
Jun 22 - Jun 25
found 8 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Hyatt Place Milford / New Haven
Price was $495, price is now $420 per person
$420
per person
Jun 22 - Jun 25
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Top Chester hotels deals
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $107 total per night
$107 total
Apr 28 - Apr 29
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
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
Microtel Inn & Suites by Wyndham Uncasville Casino Area
1954 Norwich New London Tpke Montville CT
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $83 total per night
$83 total
Apr 26 - Apr 27
Total with 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
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
2255 Norwich-New London Turnpike Montville CT
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $134 total per night
$134 total
Apr 26 - Apr 27
Total with taxes and fees
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.
Inn at Middletown
70 Main Street Middletown CT
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $215 total per night
$215 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Regency Inn & Suites New London, Mystic
269 North Frontage Road New London CT
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $97 total per night
$97 total
Apr 27 - Apr 28
Total with taxes and fees
A casino and an indoor pool are featured at this hotel. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and free perks like buffet breakfast and free self parking.
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.
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.
Frequently asked questions
Photos of local treasures
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