Winthrop Holidays from £1,102
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Your Winthrop Holiday
There's no better way to escape than with one of our holiday packages to Winthrop. The rich history and coastal scenery are a couple of the countless reasons to visit this captivating city. Fill your free time with tours of Boston Common, Faneuil Hall Marketplace and Copley Place, some of the top attractions you simply have to see during your trip to Winthrop. Check out Expedia's extensive range of travel options and start planning your ideal holiday to Winthrop now.
Top Winthrop Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
£1,102
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Great hotel at a terrific site. The North End restaurants and Faneuil Hall are both at walkable distances. Everywhere we were in the Hotel there was always a staff member asking if we needed help. We loved out stay at the Boston Harbor Hotel.
Reviewed on 22 Sept 2026
Raffles Boston
Back Bay
£1,206
per person
24 Nov - 29 Nov
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (312 reviews)
The room is beautiful, minimalist, luxurious, and extremely comfortable. In my opinion, it’s perfect for a solo traveler or, especially, for a couple. Since the room is on the smaller side, I personally wouldn’t consider it ideal for families traveling with children.
For a romantic getaway, however, it was absolutely perfect. One of the highlights is having an incredible and highly sought-after restaurant right inside the building. The dining experience was exceptional — the food was impeccable, the atmosphere was beautiful, and it truly added another level to our stay. I highly recommend making the restaurant part of the experience.
To make our stay even more special, I hired a local company, Our Love Box (@ourlovebox on Instagram), to create a romantic surprise in the room. I ordered a gorgeous bouquet of 100 roses along with a full romantic room setup, and the result was absolutely stunning.
What impressed me even more was how seamless everything was. They handled the entire setup and came back the following day to remove all of the decorations. Once they were finished, you couldn’t even tell there had been a setup in the room — everything was left exactly as it was before.
Overall, the entire experience was incredible. Between the luxurious and comfortable room, the exceptional dining experience, and the romantic setup, it was truly memorable. I highly recommend this experience for couples celebrating an anniversary, birthday, proposal, or simply looking for a special
Reviewed on 21 Sept 2026
The Kendall Hotel at the Engine 7 Firehouse
MIT
£1,740
per person
23 Nov - 28 Nov
found 9 hours ago
Return flight included
London (LHR) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Great location by Kendall T stop. Very charming hotel, wonderful staff and nice breakfast options until 10 a m.
Reviewed on 22 Sept 2026
Winthrop Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Logan Intl. Airport (BOS) |
Population | 17,600 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | New England Aquarium, Boston Museum of Fine Arts and Revere Beach |
Top hotels in Winthrop
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
£360
30 Sept - 1 Oct
includes taxes & fees
9.2/10 Wonderful! (4,828 reviews)
"Very disappointed with the cleanliness of the room, there was debris in the tub, we spent the night there to go to an event, I used the iron to press my clothes and the iron was dirty and stained my white outfit. I called for something to clean it with and another iron for the rest of my outfit but ..."
Reviewed on 22 Sept 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
£198
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (2,939 reviews)
"Only problem was that Bar was never open during my stay"
Reviewed on 22 Sept 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
£264
4 Oct - 5 Oct
includes taxes & fees
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 Winthrop attractions
Photo by The Curious Zephyr
Winthrop Beach
8.4/10 (26 reviews)
This tranquil stretch of shoreline offers panoramic views of Boston's skyline across the Atlantic. Stroll the promenade at sunrise when the soft sand and gentle waves create a perfect coastal escape.
Photo by The Curious Zephyr
Winthrop Shore Reservation
7.6/10 (5 reviews)
This Atlantic coastal retreat offers a mix of sandy and pebbly shores with stunning Boston skyline views. Enjoy morning walks along the promenade when the beach is serene and the sea breeze most refreshing.
Point Shirley Beach
8.0/10 (7 reviews)
Why not spend a lazy afternoon at Point Shirley Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.
Donovan Beach
7.6/10 (4 reviews)
This intimate sandy spot offers stunning Boston skyline views and a unique vantage point for watching planes from Logan Airport. Bring a picnic to enjoy while aircraft soar dramatically overhead.
What to do in Winthrop
Boston Old Town Trolley Hop-on Hop-Off City Tour
£36
per adult
90% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
£52
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
£34
per adult
80% of travellers recommend
Frequently asked questions
How much does a Winthrop travel package cost?
Be ready to book, because a getaway to Winthrop starts from only £1,102. When you combine your flights, hotels and car rentals into a travel package, you'll pick up great deals.
If I'm not able to travel, can I cancel my Winthrop travel package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a Winthrop travel package and need to cancel or amend it, we can help. It's always worth browsing our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may charge a fee.
How do I get a cheap travel package to Winthrop?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you a few dollars too. A Winthrop travel package makes it a breeze to arrange your dream adventure. With more than 550 airlines throughout the world to select from, finding convenient flights that suit your schedule will be no sweat. On top of that, we have over 1,000,000 hotel options globally to choose from. Talk about choice! Whatever your budget, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Winthrop holidays?
Expedia has joined forces with online lender Klarna to make your next break easier on your wallet. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more money to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that suits your budget. Take a look at these flexible payment options:
- Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable monthly instalment plans. If paying small amounts each month works for you, pick this option at checkout.
- Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
- Low deposit holidays: When you stumble on an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.
Where should I stay in Winthrop?
With interesting attractions such as Revere Beach and East Boston Memorial Stadium in this area, see if you can find a hotel near either one. Belle Isle Marsh Reservation is another sight that pulls the crowds.
What are the top hotels in Winthrop?
Get your holiday off to a flying start by booking a room at Boston Park Plaza. It's one of most sought-after properties in Winthrop. Another top option is Embassy Suites Boston Logan Airport.
How far in advance should I book my Winthrop holiday?
To score rock-bottom prices, book nice and early. Air carriers usually begin selling tickets, along with some of the lowest fares, around 12 months ahead of time. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Winthrop, there are always lots of great deals on Expedia. Check them out now!
What does an Expedia Winthrop travel package include?
Hotels, flights and rental cars, or any combination of them — it's your pick! Whether you're venturing to Winthrop with the family or travelling by yourself, there's a bundle to fit every style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a Winthrop travel package?
A package can be easier on the credit card than separately booking all you need for your adventure. For example, combine your flights, hotels and rental cars and save a packet. Whatever sort of holiday you're planning, you're sure to find a package that's perfect for you.
Can I choose my airline with a Winthrop Expedia travel package?
You can, and with over 550 airlines to choose from across the globe, you have plenty of choice. Scroll through the available options and find out 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.
