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Winchester Vacation Packages

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Winchester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Save 100% on your flight
Price was $662, price is now $482 per person
$482
per person
Feb 12 - Feb 15
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rundlet-May House and John Paul Jones House Museum are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Price was $2,173, price is now $1,155 per person
$1,155
per person
Feb 9 - Feb 14
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.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
Price was $1,592, price is now $952 per person
$952
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 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 Charles Hotel

The Charles Hotel

4 out of 5
Save 100% on your flight
Price was $921, price is now $606 per person
$606
per person
Feb 18 - Feb 21
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Save 100% on your flight
Price was $933, price is now $683 per person
$683
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, room service, 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.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $800, price is now $588 per person
$588
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and New England Aquarium are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $1,257, price is now $949 per person
$949
per person
Jan 16 - Jan 19
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $892, price is now $677 per person
$677
per person
Jan 16 - Jan 19
found 15 hours 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.
The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $662, price is now $482 per person
$482
per person
Feb 12 - Feb 15
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,684, price is now $1,019 per person
$1,019
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $921, price is now $606 per person
$606
per person
Feb 18 - Feb 21
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $991, price is now $692 per person
$692
per person
Jan 29 - Feb 1
found 18 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Porter Square Hotel

Porter Square Hotel

3 out of 5
North Cambridge
Price was $733, price is now $487 per person
$487
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,173, price is now $1,155 per person
$1,155
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,592, price is now $952 per person
$952
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was $1,071, price is now $706 per person
$706
per person
Jan 8 - Jan 13
found 1 day 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.

Frontier Airlines
Wed, Jan 21 - Thu, Jan 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 21 from Los Angeles Intl. to Logan Intl., returning Thu, Jan 29, priced at $158 found 1 day ago
United
Wed, Jan 21 - Thu, Jan 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jan 21 from Los Angeles Intl. to Logan Intl., returning Thu, Jan 29, priced at $179 found 1 day ago
Delta
Mon, Apr 20 - Tue, Apr 28
PDX
Portland Intl.
BOS
Logan Intl.
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Apr 20 from Portland Intl. to Logan Intl., returning Tue, Apr 28, priced at $188 found 1 day ago
United
Sat, Dec 13 - Wed, Jan 7
PEK
Capital Intl.
BOS
Logan Intl.
$1,046 Roundtrip, found 1 day ago
$1,046
Roundtrip
found 1 day ago
Select United flight, departing Sat, Dec 13 from Capital Intl. to Logan Intl., returning Wed, Jan 7, priced at $1,046 found 1 day ago