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Holidays to Winthrop

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Winthrop choose Expedia! Find everything you need to organise your trip to Winthrop in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top flight + hotel deals in Winthrop

White Elephant Hotel
Hilton Boston Downtown/Faneuil Hall
Seaport Hotel Boston
The Godfrey Hotel Boston
Porter Square Hotel
Cambria Hotel Boston, Downtown-South Boston

Top Hotel Deals

Winthrop Beach Inn and Suites
Winthrop Beach Inn and Suites
3 out of 5
312 Shirley Street, Winthrop, MA
The price is £80 per night from 17 Apr to 18 Apr

Situated near the beach, this hotel is 2.3 mi (3.7 km) from Revere Beach and within 6 miles (10 km) of Long Wharf and Paul Revere House. Harpoon Brewery and ...

4.3/5Excellent! (966 reviews)

"Property has been renovated to look wonderful. Nevertheless, we night we arrived we realized two of the beds were broken. They nicely offered an additional room until next morning. The following morning we were able to change Reims but we lost storage space and kitchenette dining area. The kitchen ..."…"

Reviewed on 13 Mar 2020

Winthrop Beach Inn and Suites
The Winthrop Arms Hotel And Restaurant
The Winthrop Arms Hotel And Restaurant
3 out of 5
130 Grovers Ave., Winthrop, MA
The price is £126 per night from 16 Apr to 17 Apr

Located in Winthrop, this beachfront hotel is next to a golf course, 1.6 mi (2.6 km) from Revere Beach, and within 6 mi (10 km) of Long Wharf and TD Garden. ...

4.2/5Excellent! (385 reviews)

"Great location, nice room, exactly what we were looking for."…"

Reviewed on 7 Jan 2021

The Winthrop Arms Hotel And Restaurant
Château sur Mer Bed & Breakfast
Château sur Mer Bed & Breakfast
3 out of 5
100 Sargent Street, Winthrop, MA
The price is £118 per night from 16 Apr to 17 Apr

Situated in Winthrop, this bed & breakfast is 3 mi (4.8 km) from Revere Beach and within 6 miles (10 km) of TD Garden and New England Aquarium. Long Wharf and ...

4.2/5Excellent! (134 reviews)

"The room and property were quaint and comfortable."…"

Reviewed on 16 Nov 2019

Château sur Mer Bed & Breakfast
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.

Top things to do in Winthrop

Plan your Winthrop holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Winthrop. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Winthrop holiday package?
Whether it’s your hotel, flight or rental car, you can cancel and rebook it. Locked in your Winthrop holiday package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For further information, look up our Customer Service Portal. We’ll help you every step of the way.
What are the top hotels in Winthrop?
If it’s your first visit to Winthrop, reserve a room at Winthrop Beach Inn and Suites or The Winthrop Arms Hotel And Restaurant. Both hotels will make you feel at home and are favourites with many savvy travellers.
When is the best time of year to visit Winthrop?
is a great month to head to Winthrop if you’re hoping to save a few dollars. is a more expensive month by comparison, so expect to pay more if you visit then. If you’d rather give the crowds a wide berth, think about taking your trip in . However, there’s a charm to travelling in peak season. Winthrop is arguably at its finest in .
How far in advance should I book my Winthrop holiday?
Reward yourself with the widest variety and the lowest prices by booking your Winthrop holiday nice and early. Air carriers usually release flights anywhere up to a year in advance, so start locking things in as soon as you can. That being said, Expedia is committed to giving you the best bargains around, so it’s always a good time to book your dream holiday!
What should I know before booking a Winthrop travel package?
You’ll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and enjoy exciting discounts. You’re not limited to hotels, though. We have oceanfront condos, cosy city apartments and even castles and houseboats!
Does Expedia offer Book Now, Pay Later Winthrop holiday packages?
Thanks to our partnership with online lender Affirm, those booking via Expedia can now pay for their flights and more in easy installments that won’t drain your wallet. Book Now, Pay Later and start your dream holiday today!