Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Sutton
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Sutton. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions Purgatory Chasm State Park and Elm Draught House Cinema are located nearby.
Lighthouse Inn
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 3-star beach hotel in West Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Bass River Lighthouse are located nearby.
Boston Lodge and Suites
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 4-star family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Sonesta Select Boston Lowell Chelmsford
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Lowell. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cambodia Town and Lowell Heritage State Park are located nearby.
Holiday Inn Express Fall River North by IHG
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Fall River. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Somerset Marina and Pierce Beach & Playground are located nearby.
DoubleTree by Hilton Hotel Boston - Westborough
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Westborough. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lake Chauncy Public Beach and Westborough Country Club are located nearby.
Quality Inn Raynham - Taunton
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Raynham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Ryan Family Amusement and Raynham Flea Market are located nearby.
An English Garden Bed & Breakfast
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 3-star beach B&B in Dennis Port. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cape Cod Theatre Company – Home of the Harwich Jr. Theatre and Sea Street Beach are located nearby.
Chester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 7 hours ago
$102
Roundtrip
found 7 hours ago
Sat, Aug 9 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 20 hours ago
$112
Roundtrip
found 20 hours ago
Fri, Jun 13 - Sun, Jun 15
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Fri, Jul 11 - Sun, Jul 13
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$189 Roundtrip, found 4 days ago
$189
Roundtrip
found 4 days ago
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