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Winchester flight + hotel packages

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Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Stay at this 5-star 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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.

Top Winchester hotels deals

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $245 per night
CA $245
CA $285 total
includes taxes & fees
Apr 13 - Apr 14
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square are located nearby.
Free WiFi
Restaurant
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $400 per night
CA $400
CA $473 total
includes taxes & fees
May 4 - May 5
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Pool
Pet-friendly
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
The price is CA $298 per night
CA $298
CA $347 total
includes taxes & fees
Apr 6 - Apr 7
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Free WiFi
Restaurant
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $243 per night
CA $243
CA $282 total
includes taxes & fees
Apr 10 - Apr 11
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.
Pet-friendly
Free WiFi
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $296 per night
CA $296
CA $394 total
includes taxes & fees
May 4 - May 5
Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Pool
Spa
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $252 per night
CA $252
CA $359 total
includes taxes & fees
Apr 13 - Apr 14
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Pet-friendly
Restaurant
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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.

Popular places to visit

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Boston Common which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 reviews)

After visiting Boston Common, make a plan to see the other sights and activities in Boston. Discover the fascinating museums in this vibrant area, or seek out the local tours.

Boston Common
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 reviews)

Walk around the campus of Harvard University, a top college in Boston. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.

Harvard University

Winchester Vacations

Are you set for your next unforgettable adventure? Ensure you don't miss out on any fun in Winchester by learning the basics about it before you jet off.

This town is 2 miles (3 kilometers) away from Woburn and 3 miles (5 kilometers) away from Stoneham.

The population of this area of Massachusetts is nearly 21,000.

Places to visit in Winchester

This town provides easy access to some excellent attractions. The Harvard University and the Semitic Museum are well worth taking a look at, so add them to your travel schedule and find out if you've got time to get to all of them.

If you want to see where the locals do much of their shopping, visit Harvard Square. Have a wander around and check out which stores they frequent the most. Want more options? Traveling can often mean wearing the same clothes day in, day out. So, if you fancy treating yourself to a snazzy new outfit, make your way over to Burlington Mall. But that's not all. If you're dying to see where the local people go to do their shopping, drop by Square One Mall. Have a look around and discover which stores they frequent the most.

Where do you fly into for Winchester?

When you're planning your upcoming Winchester trip, keep in mind that the closest airport, Logan International Airport (BOS), is about 9 miles (14 kilometers) to the southeast of the downtown area. Book your flights, pack your luggage and prepare for some awesome adventures!

Frequently asked questions

How much are vacation packages to Winchester?
Treat yourself to a memorable travel experience in Winchester with a vacation package starting at just CA $960. Reserving your flights, hotels and tours with Travelocity is so simple. And even better, our great deals will leave you with extra cash for fun.
Where can I get the best vacation package deals for Winchester?
You can pick up awesome Winchester package deals with Travelocity. Select from as many as 400 partner airlines and 1,000,000 properties worldwide and turn your travel dreams into reality.
Why should I purchase my Winchester vacation package via Travelocity?
You’ll not only enjoy big savings, but you’ll also have access to our 24/7 support, high-quality service and a Price Match Guarantee. Wander across the world, discover hidden sights and make lifelong memories — we’ll take care of the important details.
Can I save on my Winchester car rental if I bundle it with hotels and flights?
Combining your hotel, flight and car into a Winchester vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you freedom to get to all those famous sights you want to see. Sitting 64 kilometers away from Winchester, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Winchester?
Many people fly into Logan Intl. Airport (BOS), 14 kilometers southeast of downtown Winchester. Others prefer T.F. Green Airport (PVD) (88 kilometers away from central Winchester) or Manchester-Boston Regional Airport (MHT) (56 kilometers away from central Winchester).
What is there to do in Winchester?
Snap up the excellent photo-ops at Winter Pond, one of the most well-known attractions in Winchester. There’s plenty more to uncover in this exciting destination, so give yourself enough time to visit some of its hidden gems.
Where should I stay when visiting Winchester?
Many people spend their nights at the Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93. It’s sure to be a good base for your Winchester getaway.

Photos of local treasures

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