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.
Heritage Hotel, Golf & Conference Center
Price was $601, price is now $499 per person
$499
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.
Beechmont - Perfect for Family Retreat!
North End
Save 100% on your flight
Price was $2,086, price is now $1,680 per person
$1,680
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Price was $1,430, price is now $1,188 per person
$1,188
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.
Hyatus Luxury Residences City Crossing
The Hill
Price was $1,278, price is now $1,070 per person
$1,070
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.
Top Chester hotels deals
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Free Cancellation
$72 nightly
The price is $83 total per night
$83 total
Jun 18 - Jun 19
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
Hyatt Place Uncasville - Casino Area
2049 Norwich Montville CT
$105 nightly
The price is $121 total per night
$121 total
Jun 29 - Jun 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
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$314 nightly
The price is $361 total per night
$361 total
Jun 17 - Jun 18
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.
On private beach
Pool
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
$77 nightly
The price is $88 total per night
$88 total
Jun 29 - Jun 30
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$114 nightly
The price is $131 total per night
$131 total
Jul 2 - Jul 3
Total with taxes and fees
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 is 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.
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