Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Bell Inn
Price was $906, price is now $646 per person
$646
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this luxury inn in Peabody. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.
We thoroughly enjoyed our stay at the Bell Inn —our room was clean, the prices were very reasonable, and we had everything we needed nearby. Additionally, the water pressure in the shower was the best I've had in a long time.
Reviewed on Sep 2, 2026
Raffles Boston
Price was $2,636, price is now $1,664 per person
$1,664
per person
Nov 21 - Nov 27
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 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Staff and room
Reviewed on Sep 4, 2026
Battery Wharf Hotel, Boston Waterfront
Price was $1,364, price is now $876 per person
$876
per person
Nov 21 - Nov 27
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 breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.
Beautiful location and hotel
Reviewed on Sep 5, 2026
Four Seasons Hotel Boston
Price was $3,345, price is now $2,177 per person
$2,177
per person
Nov 21 - Nov 27
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 room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Mandarin Oriental, Boston
Price was $2,803, price is now $1,873 per person
$1,873
per person
Nov 21 - Nov 27
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 breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Over the top nice hotel and room was amazing!
Reviewed on Aug 31, 2026
Boston Harbor Hotel
Price was $1,255, price is now $876 per person
$876
per person
Nov 6 - Nov 8
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 Faneuil Hall Marketplace are located nearby.
Luxury Apartments by Hyatus at Boston Everett
Save 100% on your flight
Price was $12,036, price is now $8,709 per person
$8,709
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury apartment in Everett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
The Langham, Boston
Save 100% on your flight
Price was $1,859, price is now $1,371 per person
$1,371
per person
Oct 15 - Oct 18
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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
The rooms were clean, staff were polite and friendly, and location was perfect for our trip. More kid friendly that I was expecting with our 2 year old.
Reviewed on Sep 3, 2026
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, Oct 20 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$284 Roundtrip, found 5 hours ago
$284
Roundtrip
found 5 hours ago
Tue, Oct 20 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$295 Roundtrip, found 5 hours ago
$295
Roundtrip
found 5 hours ago
Tue, Nov 3 - Sat, Nov 7
PDX
Portland Intl.
BOS
Logan Intl.
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Wed, Oct 7 - Thu, Oct 29
HKG
Hong Kong Intl.
BOS
Logan Intl.
$772 Roundtrip, found 1 day ago
$772
Roundtrip
found 1 day ago
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