Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common 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.
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.
Blue Water Resort
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 resort in South Yarmouth. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Riviera Beach Resort
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Red Jacket Beach Resort
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 3.5-star beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Ocean Club on Smuggler's Beach
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Centerboard
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this hotel in Nantucket. Enjoy free WiFi, daily housekeeping, and cable TV channels. Popular attractions First Congregational Church and White Heron Theatre 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 14 hours ago
$102
Roundtrip
found 14 hours ago
Sat, Aug 9 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day 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 5 days ago
$189
Roundtrip
found 5 days ago
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