Winchester Holidays

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Top Flight + Hotel Deals in Winchester

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

The Revolution Hotel

3.5 out of 5
South End
Price was €1,430, price is now €1,251 per person
€1,251
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,993 reviews)
Hesitant because of the shared bathrooms but once we arrived we realized the place was even better in person. Multiple bathrooms so you wont worry about them being occupied when needed. Cleaning staff always doing checks and cleaning multiple times a day. Great stay would stay again.

Reviewed on 10 Nov 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was €1,791, price is now €1,431 per person
€1,431
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,501 reviews)

The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Price was €1,518, price is now €1,315 per person
€1,315
per person
11 Dec - 18 Dec
found 5 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (7,276 reviews)

Boston Marriott Copley Place

Boston Marriott Copley Place

4 out of 5
Back Bay
Price was €1,646, price is now €1,442 per person
€1,442
per person
11 Dec - 18 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.4/10 Exceptional! (1,871 reviews)
Very nice staff excellent location quiet rooms excellent food great location for all points of interest in Boston. Have stayed here three times in the last four years and it always delivers highly recommend this hotel.

Reviewed on 9 Nov 2026

Sheraton Commander Hotel

Sheraton Commander Hotel

3.5 out of 5
West Cambridge
Price was €1,641, price is now €1,587 per person
€1,587
per person
11 Dec - 18 Dec
found 5 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (442 reviews)
Great access to Harvard Law, visiting our L1 son.

Reviewed on 8 Nov 2026

Top hotels in Winchester

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is €182 per night from 23 Nov to 24 Nov
€182
23 Nov - 24 Nov
includes taxes & fees
9.2/10 Wonderful! (5,009 reviews)
"Clean and comfortable. Valet staff was great. Front desk staff was friendly but failed to mention there were two separate parts of the hotel and were accessed by different elevators. We went to the correct floor only to find our room didn’t exist. We went back to the lobby and realized we were on ..."

Reviewed on 9 Nov 2026

Omni Boston Hotel at the Seaport
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 €112 per night from 23 Nov to 24 Nov
€112
23 Nov - 24 Nov
includes taxes & fees
9/10 Wonderful! (3,029 reviews)
"Hesitant because of the shared bathrooms but once we arrived we realized the place was even better in person. Multiple bathrooms so you wont worry about them being occupied when needed. Cleaning staff always doing checks and cleaning multiple times a day. Great stay would stay again."

Reviewed on 10 Nov 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is €183 per night from 22 Nov to 23 Nov
€183
22 Nov - 23 Nov
includes taxes & fees
Seaport Hotel Boston
See all 4,060 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.

Stay near popular Winchester attractions

Winter Pond

9.0/10 (2 reviews)
Winter Pond offers a tranquil escape as Massachusetts' northernmost Coastal Plain Pondshore Community. Bring binoculars to spot diverse bird species while strolling along its peaceful shores.
See properties

What to do in Winchester

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

€44
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
View Boston Observation Deck General Admission

View Boston Observation Deck General Admission

€30
per adult
View Boston Observation Deck General Admission
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

€63
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices from €1,251 on Expedia for your Winchester break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
Plan your trip for the shoulder or low season and you're likely to find cheap Winchester holiday packages. Keep in mind that public holidays and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Winchester?
Usually, a handful of days is enough to check out the major attractions during your Winchester holiday. But if you'd like to have some time to rest or take day tours, think about extending your trip.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Winchester package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester adventure off to a flying start.
Is it cheaper to book a Winchester holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalised Winchester holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Winchester?
Score incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Winchester getaway.
How to plan a trip to Winchester?

  1. Choose your travel dates: The things you'd like to do in Winchester and your favourite season will help you decide when to go.
  2. Set your budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Winchester. Then, pick a hotel that works with your budget, whether that's an affordable option or a more luxurious retreat.
  3. Decide how many days away: Start by listing all the attractions you want to experience in Winchester. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right Winchester holiday package for you.

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