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Winchester flight + hotel packages

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Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 12 - Jul. 15
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jul. 12 - Jul. 15
Roundtrip flight included
Toronto (YYZ) 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.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Jul. 12 - Jul. 15
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 12 - Jul. 15
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 2 restaurants. Popular attractions Copley Square and Boston Common are located nearby.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
per person
Jul. 12 - Jul. 15
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 4.5-star 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.

Top Winchester hotels deals

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 $322 per night
CA $322
per night
May 24 - May 25
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.
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 $261 per night
CA $261
per night
May 27 - May 28
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.
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street, Newton, MA
The price is CA $183 per night
CA $183
per night
May 12 - May 13
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $245 per night
CA $245
per night
May 27 - May 28
Book a stay at this historic hotel in Boston. Enjoy 2 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
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 $254 per night
CA $254
per night
May 27 - May 28
Book a stay at this eco-certified hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and Boston Common are located nearby.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St, Boston, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $272 per night
CA $272
per night
May 27 - May 28
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
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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 acclaimed theater scene.

Harvard University
Image for New England Aquarium

New England Aquarium

4.5/5(154 reviews)

Take the family to visit the sea creatures at New England Aquarium and learn why this is a favorite attraction in Boston. Stroll along the waterfront or attend a sporting event in this vibrant area.

New England Aquarium

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?
Enjoy an unforgettable experience in Winchester with a vacation package starting at just CA $899. Booking your hotels, flights and tours with Travelocity is simple. What’s more, our deals will leave you with more money in your pocket for fun, fun, fun!
Where can I get the best vacation package deals for Winchester?
You’ll find unbeatable Winchester package deals with Travelocity. Pick from as many as 400 air carriers and 665,000 properties worldwide and turn those travel fantasies into a reality.
Why should I book my Winchester vacation bundle with Travelocity?
We’ve got round-the-clock support, top-notch service and a Price Match Guarantee. Life’s a great big journey — and we have alluring destinations for you to journey to all across the world. Explore with us and your bank balance will thank you for it.
Can I save on my Winchester car rental if I bundle it with hotels and flights?
Certainly — bundle your hotel, car and flight into a Winchester vacation package and you can save tons. With so much to uncover in and around Winchester, having your own set of wheels will make exploring easy. Once you’re behind the wheel, crank up the tunes and cruise toward Plymouth Rock, a well-known sight about 69 kilometersfrom Winchester.
What is the best time of year to go to Winchester?
Vacationing in the low season, , comes with a swag of benefits — think more cost-effective airfares and hotels and less bumping shoulders with tourist crowds. But there’s an undeniable magic in the air during the busiest season. More events will be on and more attractions will be open in . If you’re trying to save, usually offers the lowest hotel prices. You’ll pay more for a bed in .
Which airport is best for Winchester?
Boston, MA (BOS-Logan Intl.) is a major hub. It’s located approximately 14 kilometerssoutheast of Winchester. Other options worth checking out are Providence, RI (PVD-T.F. Green) (85 kilometersaway from central Winchester) and Manchester, NH (MHT-Manchester-Boston Regional) (60 kilometersaway from central Winchester).
What is there to do in Winchester?
You’ll find some great photo opportunities at Winter Pond, one of the most well-known attractions in Winchester. There’s so much more to discover in this exciting city, so give yourself enough time to see some of its hidden gems.
Where should I stay when visiting Winchester?
If you’re searching for someplace comfortable to lay your head, have a look at the Private Room in Shared Apartment, Free Wifi and Parking, no Hidden Fees. It’s the top choice for many visitors.
Can I go on vacation to Winchester at this time?
Find out all the info that’s important relating to travel restrictions and quarantine policies ahead of your flight to Winchester. Our Covid-19 Travel Advisor is full of advice to help make your vacation relaxed and hassle-free.