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Winchester flight + hotel packages

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Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Dec. 8 - Dec. 13
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
Stay at this 4-star 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.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Jan. 10 - Jan. 17
found 13 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
Stay at this 5-star 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.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Dec. 8 - Dec. 13
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
Book a stay at this eco-certified hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
The Boxer

The Boxer

4 out of 5
West End
Save 100% on your flight
per person
Jan. 10 - Jan. 17
found 13 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Jan. 10 - Jan. 17
found 13 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Top Winchester hotels deals

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 $236 per night
CA $236
CA $282 total
includes taxes & fees
24 Nov - 25 Nov
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 Boston Common are located nearby.
Pool
Pet-friendly
Omni Parker House

Omni Parker House

4 out of 5
60 School St, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $217 per night
CA $217
CA $301 total
includes taxes & fees
25 Nov - 26 Nov
Book a stay at this eco-certified hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and New England Aquarium are located nearby.
Pet-friendly
Free WiFi
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $187 per night
CA $187
CA $299 total
includes taxes & fees
28 Nov - 29 Nov
Stay at this 4-star historic hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Pet-friendly
Free WiFi
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4.5 out of 5
450 Summer Street, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $204 per night
CA $204
CA $286 total
includes taxes & fees
25 Nov - 26 Nov
Stay at this 4.5-star 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. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Pool
Spa
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street, Newton, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $122 per night
CA $122
CA $136 total
includes taxes & fees
24 Nov - 25 Nov
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Pool
Pet-friendly
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 $278 per night
CA $278
CA $388 total
includes taxes & fees
17 Nov - 18 Nov
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

Image for Fenway Park

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
Image for Harvard University

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 fascinating museums.

Harvard University
Image for Boston Common

Boston Common

4.5/5(518 reviews)

Explore the great outdoors with a trip to Boston Common, a popular green space in Boston. Discover the fascinating museums and notable monuments in this vibrant area.

Boston Common

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 $741. 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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