Search Deals on
Winchester Vacation Packages

Build your package with 2 more options

Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
Save 100% on your flight
Price was $356, price is now $196 per person
$196
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 3.5-star business-friendly hotel in Boston. Enjoy free breakfast, a free airport shuttle, and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Boston Harbor and New England Aquarium are located nearby.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $1,942, price is now $771 per person
$771
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 4-star 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.
Raffles Boston

Raffles Boston

5 out of 5
Price was $980, price is now $490 per person
$490
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Price was $840, price is now $438 per person
$438
per person
Dec 29 - Jan 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 4-star 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 Boston Common and TD Garden are located nearby.
The Newbury Boston

The Newbury Boston

5 out of 5
Price was $1,412, price is now $763 per person
$763
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
Save 100% on your flight
Price was $477, price is now $261 per person
$261
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Save 100% on your flight
Price was $564, price is now $315 per person
$315
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $354, price is now $199 per person
$199
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 3.5-star hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
Jeffries Point
Save 100% on your flight
Price was $356, price is now $196 per person
$196
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $980, price is now $490 per person
$490
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was $840, price is now $438 per person
$438
per person
Dec 29 - Jan 1
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $829, price is now $466 per person
$466
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $1,942, price is now $771 per person
$771
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,305, price is now $960 per person
$960
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $2,210, price is now $1,131 per person
$1,131
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was $1,970, price is now $1,059 per person
$1,059
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Wed, Dec 3 - Tue, Dec 9
PDX
Portland Intl.
BOS
Logan Intl.
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Dec 3 from Portland Intl. to Logan Intl., returning Tue, Dec 9, priced at $161 found 1 day ago
Delta
Fri, Dec 5 - Mon, Dec 8
LAX
Los Angeles Intl.
BOS
Logan Intl.
$209 Roundtrip, found 21 hours ago
$209
Roundtrip
found 21 hours ago
Select Delta flight, departing Fri, Dec 5 from Los Angeles Intl. to Logan Intl., returning Mon, Dec 8, priced at $209 found 21 hours ago
Hainan Airlines
Wed, Dec 3 - Sun, Dec 28
PVG
Pudong Intl.
BOS
Logan Intl.
$908 Roundtrip, found 3 hours ago
$908
Roundtrip
found 3 hours ago
Select Hainan Airlines flight, departing Wed, Dec 3 from Pudong Intl. to Logan Intl., returning Sun, Dec 28, priced at $908 found 3 hours ago
Hainan Airlines
Wed, Dec 3 - Wed, Dec 24
PEK
Capital Intl.
BOS
Logan Intl.
$992 Roundtrip, found 15 hours ago
$992
Roundtrip
found 15 hours ago
Select Hainan Airlines flight, departing Wed, Dec 3 from Capital Intl. to Logan Intl., returning Wed, Dec 24, priced at $992 found 15 hours ago