Winter Hill Holidays from £921

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Your Winter Hill Holiday

Organising your next break just got easier with a holiday package to Winter Hill. Embrace the best this neighbourhood has to offer while making fond memories that'll stay with you for years. When it's time to take in the sights, you'll find lots of top attractions nearby including Assembly Row, LEGOLAND® Discovery Centre and Somerville Theatre. Visit one, two or more during your trip to Winter Hill. No matter what your dream Winter Hill holiday looks like, you can turn it into reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was £1,336, price is now £921 per person
£921
per person
6 Oct - 13 Oct
found 3 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on 25 Aug 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £1,923, price is now £1,143 per person
£1,143
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on 24 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £1,776, price is now £1,168 per person
£1,168
per person
27 Oct - 30 Oct
found 21 hours ago
Return flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on 20 Aug 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
Price was £1,817, price is now £1,262 per person
£1,262
per person
25 Oct - 31 Oct
found 18 hours ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on 17 Aug 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was £1,862, price is now £1,314 per person
£1,314
per person
9 Oct - 12 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
The Langham is a wonderful, luxurious family hotel. The staff were absolutely lovely and made a fuss over our young daughter which seems rare at hotels these days. The location of the hotel is also fantastic, as it's within walking distance to both the Boston Children’s Museum and the aquarium. The indoor pool was a fantastic added bonus that our family thoroughly enjoyed. We were so impressed with our experience that we will definitely be staying at The Langham again the next time we are in Boston.

Reviewed on 21 Aug 2025

Where to stay in Winter Hill

Find the best Winter Hill areas and neighborhoods for the activities you enjoy most. Learn more about Winter Hill
Downtown Boston which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Winter Hill

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 £135 per night from 1 Sept to 2 Sept
£135
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (3,273 reviews)
"Our second stay at the Seaport Hotel and everything was amazing. We will continue to use this hotel for all of our Boston visits."

Reviewed on 24 Aug 2025

Seaport Hotel Boston
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 £185 per night from 1 Sept to 2 Sept
£185
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (3,866 reviews)
"Rooftop pool was great!"

Reviewed on 25 Aug 2025

Omni Boston Hotel at the Seaport
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 £167 per night from 1 Sept to 2 Sept
£167
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (3,692 reviews)
"Decor and furnishings unique. Refreshing and different. View from lounge area of Boston skyline is amazing!"

Reviewed on 24 Aug 2025

citizenM Boston North Station
See all 3,716 properties in Winter Hill
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

Frequently asked questions

How much does a Winter Hill travel package cost?
We make it simple for everyone to travel, with Winter Hill packages starting from as low as £921. You'll have the flexibility to combine your favourite airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and activities to your travel itinerary?
If I'm not able to travel, can I cancel my Winter Hill travel package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or amend your Winter Hill travel package at no cost within 24 hours of booking. However, you may be charged a fee by your hotel, airline or car rental company for older bookings. If life throws you a curveball, take a look at our Customer Service Portal for further information.
How do I get a cheap travel package to Winter Hill?
Lock in flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Winter Hill travel package. It's as simple as that! From flights and hotels to activities and rental cars, Expedia makes travelling on a budget easy. And with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later Winter Hill holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fabulous getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can book that well-deserved holiday sooner.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: Hitting the "book now" button is much easier with this plan. Put down a small deposit on your escape and then start working on your travel itinerary.

Where should I stay in Winter Hill?
With popular attractions like LEGOLAND® Discovery Centre and Somerville Theatre in this area, try to find a hotel near either one. Assembly Row is another Winter Hill sight that visitors flock to.
What are the top hotels in Winter Hill?
If it's your first visit to Winter Hill, reserve a room at Holiday Inn Boston Bunker Hill Area, an IHG Hotel or The Row Hotel at Assembly Row, Autograph Collection. Both have good amenities and are favourites with many savvy travellers.
How far in advance should I book my Winter Hill holiday?
Search Expedia to compare international flights as early as possible. You can normally purchase a ticket up to 12 months before departure. If you can't see your preferred carrier, or you have to book last minute, don't worry. Cheap fares to Winter Hill sometimes appear just weeks before departure.
What does an Expedia Winter Hill travel package include?
Flights, rental cars and hotels, or any combination of them — you decide! Whether you're visiting Winter Hill with the family or travelling solo, there's a package to match every style and budget. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking a Winter Hill travel package?
You'll pick up terrific savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together simply makes planning easier. So why waste your money or time? Whether you're organising a luxury city stay with your love or a budget family adventure, explore our package deals today.
Can I choose my airline with a Winter Hill Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Simply select the carrier you want and create the perfect Winter Hill holiday.

Popular places to visit

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

Fenway Park

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

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

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

Things to do

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 Boston

* 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.