Winthrop Holidays from £1,005

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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.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Price was £1,414, price is now £1,005 per person
£1,005
per person
30 Apr - 7 May
found 22 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9/10 Wonderful! (2,215 reviews)
Amazing place, great amenities, they help us so much during a terrible storm, we could not have chosen a better place to stay

Reviewed on 5 Feb 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was £2,086, price is now £1,310 per person
£1,310
per person
1 May - 8 May
found 3 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on 21 Oct 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,355, price is now £1,523 per person
£1,523
per person
30 Apr - 4 May
found 20 hours ago
Return direct flight included
Glasgow (GLA) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on 25 Jan 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £4,102, price is now £2,875 per person
£2,875
per person
30 Apr - 7 May
found 22 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Everything was great — room was immaculate, hotel was very nice. Would return!

Reviewed on 1 Feb 2026

Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Price was £1,536, price is now £1,084 per person
£1,084
per person
1 May - 8 May
found 3 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
6.8/10 (173 reviews)
The room is clean and the furniture is pretty, but since it's part of an apartment complex, you don't have immediate help with extra sheets or heater support; so first two days out 4, we had to deal with the cold of the room. Third and 4th, since we had called for help, they did left the extra sheets and fixed the thermostat.

Reviewed on 6 Dec 2025

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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is £119 per night from 19 Feb to 20 Feb
£119
19 Feb - 20 Feb
includes taxes & fees
8.2/10 Very Good! (3,108 reviews)
Beautiful lobby, comfortable room, excellent gym!

Reviewed on 1 Feb 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is £92 per night from 19 Feb to 20 Feb
£92
19 Feb - 20 Feb
includes taxes & fees
9.2/10 Wonderful! (6,217 reviews)
Nice staff, great room and bathroom and location is easy to walk everywhere. One of the hotels with a cheaper parking rate as well which is a plus.

Reviewed on 6 Feb 2026

Harborside Inn Of Boston
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 £55 per night from 9 Feb to 10 Feb
£55
9 Feb - 10 Feb
includes taxes & fees
9/10 Wonderful! (2,446 reviews)
I would stay here again. Great location,nice bar/restaunt

Reviewed on 5 Feb 2026

The Revolution Hotel
See all 4,263 properties in Winthrop
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

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
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
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

What to do in Winthrop

Boston Hop-On Hop-Off Trolley Tour

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

£39
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£59
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

£17
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Winthrop

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* 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.