Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ashworth by the Sea
Price was $871, price is now $624 per person
$624
per person
May 28 - Jun 2
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hampton Beach and Hampton Beach Casino are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,190, price is now $767 per person
$767
per person
May 29 - Jun 1
found 12 hours ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Lexington Battle Green and Burlington Mall are located nearby.
Boston Harbor Hotel
Save 100% on your flight
Price was $4,560, price is now $3,066 per person
$3,066
per person
May 4 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this 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 Common are located nearby.
Omni Boston Hotel at the Seaport
Save 100% on your flight
Price was $1,078, price is now $736 per person
$736
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Hyatt Regency Boston/Cambridge
Save 100% on your flight
Price was $1,358, price is now $927 per person
$927
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
The Colonnade Hotel Back Bay
Save 100% on your flight
Price was $1,389, price is now $949 per person
$949
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Fairmont Copley Plaza, Boston
Price was $992, price is now $683 per person
$683
per person
Apr 24 - Apr 27
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Langham, Boston
Save 100% on your flight
Price was $1,677, price is now $1,217 per person
$1,217
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and Boston Common 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, Apr 14 - Tue, Apr 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$216 Roundtrip, found 2 hours ago
$216
Roundtrip
found 2 hours ago
Tue, Apr 14 - Tue, Apr 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$245 Roundtrip, found 2 hours ago
$245
Roundtrip
found 2 hours ago
Sat, May 23 - Wed, Jun 10
PDX
Portland Intl.
BOS
Logan Intl.
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Sun, Sep 6 - Wed, Sep 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$256 Roundtrip, found 6 hours ago
$256
Roundtrip
found 6 hours ago
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