Winchester Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Winchester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
North End
$1,015
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Harrisburg (MDT) 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.
A/C not working. The hotel was trying to get a temporary system running but it was not ready and the room was 77 degrees on a warm evening. We were not told the a/c was not functional until we arrived, even though I called in the morning to ask if early check in was available. I had reserved a waterview suite as an anniversary surprise. While we were offered a refund, we had to call Hotels.com on our own (they were helpful) and book another hotel. A big disappointment and waste of time
Reviewed on Sep 8, 2026
Boston Harbor Hotel
North End
$1,486
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Harrisburg (MDT) 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.
Excellent overall. Great service and great location.
Reviewed on Sep 7, 2026
Raffles Boston
Back Bay
$1,281
per person
Nov 15 - Nov 19
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Mandarin Oriental, Boston
Back Bay
$1,517
per person
Nov 15 - Nov 19
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Great hotel in great location.
Staff earned five star status.
Reviewed on Sep 6, 2026
The Colonnade Hotel Back Bay
Back Bay
$1,459
per person
Oct 21 - Oct 25
found 4 hours ago
Roundtrip flight included
Tampa (TPA) 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.
We had a wonderful stay at this hotel! The staff was friendly and welcoming, and there was always someone at the door ready to greet us and help whenever needed.
We stayed for a week and really appreciated that our room was cleaned every day. It seems like many hotels no longer provide daily housekeeping unless you specifically request it, so this was a really nice touch. The room was very comfortable, and we felt right at home throughout our stay.
The location was fantastic. The subway station was right on the corner, which made it incredibly convenient to get everywhere we wanted to go. Fenway Park was only a 20-minute walk away, and we loved exploring Newbury Street, with all of its great shopping and restaurants.
We would definitely recommend this hotel, especially for its comfort, friendly staff, and excellent location. We would happily stay here again!
Reviewed on Sep 8, 2026
Encore Boston Harbor
$1,081
per person
Nov 15 - Nov 19
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) 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 Encore Boston Harbor and TD Garden are located nearby.
The hotel it self is beautiful I always enjoy staying here.but I was disappointed that the majority of the restaurants where closed that was kind of a let down and there was no room service available either
Reviewed on Sep 8, 2026
Winchester Vacation Packages
Trying to figure out a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Winchester vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Winchester the best one yet. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. We have a huge choice of flights and lodgings, and local things to do to pull from.
Winchester Hotels
With 4157 hotels and resorts in Winchester to choose from, you will find one that is perfect for you.
From Winchester hotels with pools and on-site restaurants, to boutique accommodations that add all the extra amenities, you'll find a hotel here that will make your trip one to remember. With AARP Travel Center's Winchester hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Winchester
Winchester has about 22,417 people that call this city their home. If you needed a break from the hustle and bustle of a big city, then you picked the right town. With the city's thriving artistic community and plenty of interest for history buffs you may have a hard time fitting everything into one trip.
If you need more suggestions, then make sure to click on AARP's "Things to Do" page.
Book Together and Save
As an AARP Member, you can benefit from all the great savings. You can save on select hotels worldwide, flights, and also car rentals. No matter what Winchester vacation bundle you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Book today and get ready for your Winchester vacation.
Top Hotel Deals
Seaport Hotel Boston
1 Seaport Lane Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
The Revolution Hotel
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
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. ...
Encore Boston Harbor
1 Broadway Everett MA
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 ...
Harborside Inn Of Boston
185 State St Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. ...
The Midtown Hotel MOD Collection by Sonesta
220 Huntington Avenue Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
The Dagny Boston
89 Broad Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...
citizenM Boston Back Bay
408 Newbury street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square are located ...
citizenM Boston North Station
70 Causeway Street Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
Omni Parker House
60 School St Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
Arcadian Hotel
1200 Beacon St Brookline MA
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 ...
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant ...
The Godfrey Hotel Boston
505 Washington Street Boston MA
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 ...
The Westin Copley Place, Boston, a Marriott Hotel
10 Huntington Ave Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy 5 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
The Royal Sonesta Boston
40 Edwin H. Land Boulevard Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 28 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$319
Roundtrip
found 1 day ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$331
Roundtrip
found 7 hours ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$335
Roundtrip
found 2 days ago
Mon, Oct 26 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$344
Roundtrip
found 2 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$357
Roundtrip
found 7 hours ago
Best points of interest in Boston
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