Deals on vacations and trips to Chester
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Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott New Haven Orange-Milford
Price was $295, price is now $272 per person
$272
per person
Feb 20 - Feb 23
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Beechmont - Perfect for Family Retreat!
North End
Save 100% on your flight
Price was $2,412, price is now $1,355 per person
$1,355
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Homewood Suites by Hilton Orange New Haven
Price was $348, price is now $326 per person
$326
per person
Feb 20 - Feb 23
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features an indoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop and a safe deposit box are also provided.
Clarion Inn
Price was $503, price is now $477 per person
$477
per person
Mar 29 - Mar 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
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.
Whitney Inn & Suites
Price was $486, price is now $467 per person
$467
per person
Mar 29 - Mar 31
found 1 day 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. Express check-in, express check-out, and luggage storage are also on offer.
Top Chester hotels deals
Mohegan Sun
1 Mohegan Sun Boulevard Montville CT
$211 nightly
The price is $239 total per night
$239 total
Feb 1 - Feb 2
Total with 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 Montville CT
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $107 total per night
$107 total
Feb 2 - Feb 3
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
Holiday Inn Norwich by IHG
10 Laura Blvd Norwich CT
Free Cancellation
$85 nightly
The price is $98 total per night
$98 total
Feb 10 - Feb 11
Total with 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
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Free Cancellation
$65 nightly
The price is $75 total per night
$75 total
Jan 21 - Jan 22
Total with 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
Microtel Inn & Suites by Wyndham Uncasville Casino Area
1954 Norwich New London Tpke Montville CT
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $77 total per night
$77 total
Feb 1 - Feb 2
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
Hampton Inn Norwich
154 Salem Turnpike Norwich CT
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $126 total per night
$126 total
Jan 21 - Jan 22
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. Relax with a drink at the bar/lounge and enjoy free perks like self-serve 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
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
Photos of local treasures
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