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
per person
Jun 13 - Jun 16
found 6 hours ago
Roundtrip flight included
Myrtle Beach (MYR) 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.
The Surfside Hotel
Lordship
Save 100% on your flight
per person
Jul 12 - Jul 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
A restaurant, free self parking, and wedding services are among this hotel's amenities. WiFi in public areas is free. Luggage storage is also provided.
Luxury Apartments by Hyatus at Pierpont
The Hill
per person
Jun 13 - Jun 16
found 6 hours ago
Roundtrip flight included
Myrtle Beach (MYR) 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.
Hilton Garden Inn Milford
per person
Jun 13 - Jun 16
found 6 hours ago
Roundtrip flight included
Myrtle Beach (MYR) to New Haven (HVN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Top Chester hotels deals
Hyatt Place Uncasville - Casino Area
2049 Norwich, New London Turnpike, Montville, CT
Free Cancellation
Reserve now, pay when you stay
The price is $145 per night
$145
includes taxes & fees
$126 per night
May 8 - May 9
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
Free Cancellation
Reserve now, pay when you stay
The price is $231 per night
$231
includes taxes & fees
$204 per night
Jun 2 - Jun 3
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
Clarion Inn
201 Washington Avenue, North Haven, CT
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
includes taxes & fees
$96 per night
May 27 - May 28
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
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
2255 Norwich-New London Turnpike, Montville, CT
Free Cancellation
Reserve now, pay when you stay
The price is $148 per night
$148
includes taxes & fees
$129 per night
May 4 - May 5
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
Microtel Inn & Suites by Wyndham Uncasville Casino Area
1954 Norwich New London Tpke, Route 32, Montville, CT
Free Cancellation
Reserve now, pay when you stay
The price is $87 per night
$87
includes taxes & fees
$76 per night
May 6 - May 7
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
The price is $96 per night
$96
includes taxes & fees
$83 per night
May 11 - May 12
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Pet friendly
Parking 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
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.
Photos of local treasures
Browse Chester vacation photos for more inspiration
Top all inclusive vacation packages with airfare
Book a vacation to Chester
Most popular
Hotels
Cheap Hotels in East HartfordCheap Hotels in WaterburyCheap Hotels in GrotonCheap Hotels in New HavenCheap Hotels in West HartfordCheap Hotels in FairfieldCheap Hotels in SouthingtonCheap Hotels in NorwalkCheap Hotels in SheltonCheap Hotels in WallingfordCheap Hotels in StamfordCheap Hotels in GlastonburyCheap Hotels in NorwichCheap Hotels in ManchesterCheap Hotels in VernonCheap Hotels in BristolCheap Hotels in BridgeportCheap Hotels in HartfordCheap Hotels in DanburyCheap Hotels in MilfordCheap Hotels in Mystic
Flights