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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $509, price is now $329 per person
$329
per person
Mar 20 - Mar 23
found 12 hours ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,334, price is now $859 per person
$859
per person
Mar 6 - Mar 9
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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Save 100% on your flight
Price was $977, price is now $646 per person
$646
per person
Apr 28 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Save 100% on your flight
Price was $568, price is now $396 per person
$396
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Save 100% on your flight
Price was $734, price is now $514 per person
$514
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
Price was $866, price is now $615 per person
$615
per person
Mar 6 - Mar 9
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 $681, price is now $487 per person
$487
per person
May 1 - May 3
found 23 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.
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $624, price is now $447 per person
$447
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $509, price is now $329 per person
$329
per person
Mar 20 - Mar 23
found 12 hours ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,334, price is now $859 per person
$859
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $977, price is now $646 per person
$646
per person
Apr 28 - May 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Boston (BOS)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $568, price is now $396 per person
$396
per person
Mar 6 - Mar 9
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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $901, price is now $589 per person
$589
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $1,028, price is now $652 per person
$652
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,030, price is now $713 per person
$713
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Omni Parker House

Omni Parker House

4.5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,012, price is now $716 per person
$716
per person
Apr 6 - Apr 11
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.

Delta
Wed, Mar 11 - Wed, Mar 25
LAX
Los Angeles Intl.
BOS
Logan Intl.
$179 Roundtrip, found 9 hours ago
$179
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Mar 11 from Los Angeles Intl. to Logan Intl., returning Wed, Mar 25, priced at $179 found 9 hours ago
American Airlines
Mon, Apr 20 - Tue, Apr 28
PDX
Portland Intl.
BOS
Logan Intl.
$180 Roundtrip, found 8 hours ago
$180
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, Apr 20 from Portland Intl. to Logan Intl., returning Tue, Apr 28, priced at $180 found 8 hours ago
JetBlue Airways
Tue, Feb 24 - Sun, Mar 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Feb 24 from Los Angeles Intl. to Logan Intl., returning Sun, Mar 1, priced at $184 found 1 day ago
Hainan Airlines
Tue, Feb 17 - Wed, Mar 4
FOC
Changle Intl.
BOS
Logan Intl.
$1,010 Roundtrip, found 9 hours ago
$1,010
Roundtrip
found 9 hours ago
Select Hainan Airlines flight, departing Tue, Feb 17 from Changle Intl. to Logan Intl., returning Wed, Mar 4, priced at $1,010 found 9 hours ago