Winter Hill Holidays from £650

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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was £1,339, price is now £650 per person
£650
per person
4 Feb - 8 Feb
found 17 hours ago
Return flight included
London (LON) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on 17 Oct 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was £2,410, price is now £1,277 per person
£1,277
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
All the staff was very helpful and responsive I would recommend this hotel to everyone planning to stay in Boston.

Reviewed on 9 Nov 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was £2,509, price is now £1,536 per person
£1,536
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on 9 Nov 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was £2,083, price is now £1,399 per person
£1,399
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was £1,296, price is now £904 per person
£904
per person
15 Jan - 21 Jan
found 1 day ago
Return flight included
London (LON) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)

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
Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Downtown Boston

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in Winter Hill

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 £151 per night from 22 Nov to 23 Nov
£151
22 Nov - 23 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 £85 per night from 27 Nov to 28 Nov
£85
27 Nov - 28 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 £111 per night from 24 Nov to 25 Nov
£111
24 Nov - 25 Nov
includes taxes & fees
Seaport Hotel Boston
See all 3,999 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 £650. 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.

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

£37
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

£35
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

£53
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.