Winchester Vacations from $534

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Your Winchester Vacation

The stress-free way to experience this city is with a custom-made Winchester vacation package. Base yourself in the neighborhood of Downtown Boston, which is great for nightlife, shopping and bars and pubs or choose someplace else — our packages are all about you. Fill your schedule with tours of Harvard Square, Harvard University and Bentley College, some of the top attractions you should see during your trip to Winchester. Whatever your travel plans or the size of your budget, organizing a tailored Winchester vacation is a cinch with Expedia.

The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
7.4/10 Good! (189 reviews)
The grounds are well kept. The staff are very friendly and helpful. The building itself is tired. The kitchenette had no utensils and only paper cups. Also the hot plate didn’t have a place to plug in. The fridge and microwave worked though and that’s all we needed. Just a heads up in case you need more. They had a variety of breakfast options that are included. Pancakes, waffles, eggs, muffins etc. For the price, we were happy.

Reviewed on Jun 3, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Always a great stay. Property is getting a little bit dated and could use a refresh. The house keeping staff is the best!

Reviewed on Jun 3, 2024

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
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (217 reviews)
Beautiful room, amenities, service, snacks and coffee station.

Reviewed on May 26, 2024

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Excellent experience

Reviewed on Jun 3, 2024

The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (3,580 reviews)
We've been staying at this property for more than 10 years, when it was still a Hilton. The location is ideal, the rooms are spacious and comfortable, and the service, especially Ed the doorman, is outstanding.

Reviewed on Jun 5, 2024

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
21,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

Winchester Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $216 per night from Jul 3 to Jul 4
$216
$281 total
includes taxes & fees
Jul 3 - Jul 4
9/10 Wonderful! (2,140 reviews)
Great for an overnight stay
"Room was extremely small. Did not appreciate that there were 2 towers, one practical and lower end; the other with larger rooms more amenities and higher end. I did not realize there was a difference in types of rooms until I had reserved the room. However, it was a comfortable room very comfortable ..."

Reviewed on Jun 2, 2024

Omni Boston Hotel at the Seaport
Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $182 per night from Jul 4 to Jul 5
$182
$247 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,686 reviews)
"I enjoyed staying at the historic Omni Parker House, and the staff and service were excellent. I have zero complaints, and will look forward to my next visit!"

Reviewed on Jun 5, 2024

Omni Parker House
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $143 per night from Jun 16 to Jun 17
$143
$167 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,513 reviews)
"Best property to stay at in Boston. Absolutely immaculate. You can walk anywhere from hotel."

Reviewed on Jun 3, 2024

The Revolution Hotel
See all 3,244 properties in Winchester
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
The most affordable Winchester vacation package is $534, so your dream escape can become a reality — without breaking the bank. Combine flights, hotels, car rentals and more to custom build a package suited to your traveling style.
How do I get a cheap travel package to Winchester?
Bundle your flights and hotels with Expedia to save on your next trip. With over 550 airlines and 1,000,000 hotel options across the globe, your Winchester vacation package can be tailored exactly to suit your budget. With all that extra money, why not add one or more awesome tours and activities? It’s an easy way to unlock even more bargains. Your dream vacation in Winchester is closer than you thought!
Where should I stay in Winchester?
Stay close to the action. Many travelers book hotels in the vicinity of top attractions, such as Medford Square, Winchester Hospital and Old Ship Street Historic District.
What are the top hotels in Winchester?
Whether you aim to stay for one night or a week in Winchester, you’ll get a solid night’s sleep at Sleep Up To 4 Guest New Apt. 10 Mins To Boston Easy To I. This place is a favorite with many travelers.
How far in advance should I book my Winchester vacation?
Search Expedia to compare international fares as soon as possible. You can usually purchase a ticket up to a year before departure. If it’s too early for your preferred carrier, or you’ve left things to the last moment, don’t worry. Low prices to Winchester sometimes appear within weeks of the date of departure.
What does an Expedia Winchester travel package include?
From hotels and flights to rental cars, Expedia can help you create a Winchester package that’s perfect for you. Vacationing for a week or longer? Check out a hotel, flight and rental car bundle. If you can only manage a quick getaway, a hotel and flight deal could be more your style. Tours and activities can be added once you’ve made your booking. Our travel packages make it a breeze to save and plan.
What should I know before booking a Winchester travel package?
Booking all the parts of your getaway together is one of the easiest ways to save. Bundle your flights, car rentals and hotels into a neat package. But you’re not restricted to hotels. Expedia features all types of properties, including vacation rentals such as beachside villas and city apartments. Your choices are almost endless!
Can I choose my airline with a Winchester Expedia vacation package?
Yes, you can. Expedia has access to more than 550 airline partners across the globe, so select the carrier that matches your budget and travel needs.
If I'm not able to travel, can I cancel my Winchester vacation package?
Whether it’s your hotel or flight, you can cancel or change it. Booked your Winchester vacation package in the last 24 hours? You may be able to make any changes for free. For bookings older than that, you may incur a charge from your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Winchester

Image for Fenway Park

Fenway Park

4.5/5(2,499 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Image for Harvard University

Harvard University

4.5/5(1,966 reviews)

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Image for Boston Common

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Winchester

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

$30
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
See all activities in Winchester

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.