Winchester Holidays from £826

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Your Winchester Holiday

Book a Winchester holiday package that includes everything you need and nothing you don't. Great for nightlife, shopping and bars and pubs, consider staying in the neighbourhood of Downtown Boston. A trip to Winchester is a terrific opportunity to see the sights. Be sure to look around renowned attractions like Harvard Square, Harvard University and Bentley College. Stop dreaming and start travelling. Browse the broad range of options on Expedia today and finally put your Winchester holiday plans into gear!

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
20 Oct - 24 Oct
just found
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (227 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
4 Oct - 9 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
4 Oct - 9 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Save 100% on your flight
per person
4 Oct - 9 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
Check in was very good. Property sleek and minimalist. Very clean and well maintained. Shops, restaurants a few minutes walk away. Too bad the valet gives incorrect directions to local sites.

Reviewed on 29 Jul 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
4 Oct - 9 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (413 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul 2025

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
21,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

Top hotels in Winchester

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £190 per night from 24 Aug to 25 Aug
£190
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,763 reviews)
"Was pleasantly surprised, great hotel and staff."

Reviewed on 28 Jul 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £165 per night from 10 Aug to 11 Aug
£165
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,504 reviews)
"Nice new property. Small clean modern rooms. Best for one person traveling for a short period of time. The umbrella has a check in and out. I checked it in but the employee never noted it even after asking for my room number. If I didn’t catch it I would have been charged for a $20 umbrella that ..."

Reviewed on 28 Jul 2025

citizenM Boston Back Bay
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is £152 per night from 24 Aug to 25 Aug
£152
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,604 reviews)
"We loved the close proximity to TD garden and the train station. It had all the things needed for our short trip. The room was comfortable. The shower was hot. The staff were helpful and friendly. The only thing I would warn people about is if your traveling as a couple, whomever gets the inside ..."

Reviewed on 28 Jul 2025

citizenM Boston North Station
See all 3,772 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

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

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 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
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(204 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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£58
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

£52
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

£25
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Winchester

Frequently asked questions

How much does a Winchester travel package cost?
Our Winchester packages, which start from as low as £826, are the best way to save big. All you have to do is choose your favourite flights, hotels and rental cars to create a customized getaway.
If I'm not able to travel, can I cancel my Winchester travel package?
Whether it's your flight or hotel, you can cancel and rebook it. Locked in your Winchester travel package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may incur a fee from your hotel, airline or car rental company. For more details, take a look at our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Winchester?
You'll save big if you bundle your flights, hotels and car rentals into a Winchester travel package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 hotels globally, which means you'll always have plenty of options to choose from. Eager to save even more? Add some interesting activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Expedia has teamed up with online lender Klarna to make your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more money to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your trip across multiple transactions.
  • Low deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Winchester?
Stay where the action is. Many travellers like to book hotels in the vicinity of top attractions, such as Medford Square, Arlington Friends of the Drama and Woburn Bowladrome.
What are the top hotels in Winchester?
Boston Park Plaza and Embassy Suites Boston Logan Airport are two of the most popular properties in Winchester. Why not check out the amenities and rates at each and then decide?
How far in advance should I book my Winchester holiday?
It's hard to pick the perfect time for airfares, but we normally say the earlier, the better. Most international journeys on Expedia become available to compare up to a year in advance. If you're unable to do so, don't despair. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Winchester travel package include?
That depends entirely on you. You can pick from a variety of Winchester bundles, such as a rental car, hotel and flight. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your Winchester getaway looks like, you'll save!
What should I know before booking a Winchester travel package?
A package can be easier on the hip pocket than separately booking everything you need for your getaway. For example, bundle your flights, hotels and rental cars and save a tidy sum. Whatever kind of holiday you're planning, you're sure to find a package to suit your budget.
Can I choose my airline with a Winchester Expedia travel package?
Yes, and with more than 550 airlines to select from worldwide, you have loads of choice. Look through the available options and see which airline fits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.