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 22 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 $887, price is now $571 per person
$571
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
Miami (MIA) 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 22 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 22 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 22 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 29 - Apr 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
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.
Pool
Breakfast included
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.
Pool
Breakfast included
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
Browse Chester vacation photos for more inspiration
