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.
Anchorage Inn & Suites - Portsmouth
$535
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Market Square and Water Country are located nearby.
Boston Harbor Hotel
North End
$1,997
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Wow. Just wow. What a stay. Fantastic hotel well looked after. Amazing staff so friendly and welcoming. Great location. A fabulous stay couldn ’t recommend more.
Reviewed on Sep 2, 2026
The Boxboro Regency
$555
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Boxborough. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Harvard Town Beach and Thurston's Beach are located nearby.
Ashworth by the Sea
Hampton Beach
$722
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hampton Beach and Hampton Beach Casino are located nearby.
Iris Hotel Boston
Coolidge Corner
$1,300
per person
Oct 21 - Oct 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.
This was our second stay here. Love the location and how close it is to the green line stop. Room was very comfortable and we appreciate the full fridge and microwave. perhaps my only suggestion is to put some bare essential dishes/utensils in the room.
As usual the staff were attentive to our needs, friendly and efficient. Special shout out to "Alexa" at the front desk. I forgot something in my car, and she went with me to the garage, so I was not alone since it was at night. Thank you also to the valet drivers. We had to leave at 3am on the day of our departure and they made sure our car was ready to go! Last but not least, we ate at the restaurant this time and the food was delicious! Thank you for your excellent customer service. We had a very enjoyable stay for college move-in!
Reviewed on Sep 3, 2026
enVision Hotel & Conference Center Mansfield-Foxboro
$619
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Boston (BOS)
Book a stay at this business-friendly hotel in Mansfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gillette Stadium and Xfinity Center are located nearby.
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 4178 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 ...
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. ...
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 ...
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 ...
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.
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 ...
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 ...
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 ...
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.
Fri, Sep 25 - Fri, Oct 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$258
Roundtrip
found 8 hours ago
Tue, Nov 3 - Tue, Nov 10
LAX
Los Angeles Intl.
BOS
Logan Intl.
$302
Roundtrip
found 6 days ago
Mon, Sep 21 - Tue, Sep 29
LAX
Los Angeles Intl.
BOS
Logan Intl.
$307
Roundtrip
found 1 day ago
Sat, Sep 19 - Thu, Oct 1
LAX
Los Angeles Intl.
BOS
Logan Intl.
$325
Roundtrip
found 4 days ago
Fri, Nov 13 - Mon, Nov 16
LAX
Los Angeles Intl.
BOS
Logan Intl.
$327
Roundtrip
found 17 hours ago
Best points of interest in Boston
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