Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Holly Tree Resort
Save 100% on your flight
per person
Sep 11 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Stay at this 3-star aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor are located nearby.
Sea Mist Resort
Save 100% on your flight
per person
Sep 11 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Stay at this 3-star business-friendly aparthotel in Mashpee. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Mashpee Commons and Old Indian Meetinghouse are located nearby.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Save 100% on your flight
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Stay at this 3-star beach guesthouse in East Wareham. Enjoy free WiFi, a private beach, and free bicycles on site. Popular attractions Onset Beach and Shell Point Beach are located nearby.
enVision Hotel & Conference Center Mansfield-Foxboro
Save 100% on your flight
per person
Sep 17 - Sep 23
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this business-friendly hotel in Mansfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gillette Stadium and Xfinity Center are located nearby.
Raffles Boston
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.
By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
per person
Sep 11 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Stay at this 3.5-star beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Cape Cod Inflatable Park and Sea Street Beach are located nearby.
Holiday Inn Express Boston - Saugus by IHG
Save 100% on your flight
per person
Aug 15 - Aug 21
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this business-friendly hotel in Saugus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Encore Boston Harbor and Revere Beach are located nearby.
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winchester 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.
Tue, Sep 16 - Tue, Sep 30
PDX
Portland Intl.
BOS
Logan Intl.
$159 Roundtrip, found 4 hours ago
$159
Roundtrip
found 4 hours ago
Mon, Aug 25 - Sun, Aug 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$196 Roundtrip, found 4 hours ago
$196
Roundtrip
found 4 hours ago
Mon, Jul 28 - Tue, Aug 26
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,015 Roundtrip, found 1 day ago
$1,015
Roundtrip
found 1 day ago
Mon, Aug 11 - Sat, Sep 20
PVG
Pudong Intl.
BOS
Logan Intl.
$1,248 Roundtrip, found 1 day ago
$1,248
Roundtrip
found 1 day ago
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