Winthrop Holidays from £1,078

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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.
Studio Allston Hotel

Studio Allston Hotel

4 out of 5
Brighton
Price was £1,467, price is now £1,078 per person
£1,078
per person
8 Sept - 15 Sept
found 1 hour ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
8.6/10 Excellent! (1,273 reviews)
Nice place. Would definitely stay there again if in the area

Reviewed on 22 Jun 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,279, price is now £1,420 per person
£1,420
per person
24 Aug - 28 Aug
found 9 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on 15 Jun 2026

Summer House Hotel

Summer House Hotel

2 out of 5
Save 100% on your flight
Price was £3,143, price is now £2,215 per person
£2,215
per person
8 Sept - 15 Sept
found 11 hours ago
Return flight included
London (LON) to Boston (BOS)
4/10 (1 review)
The cottages are very comfortable and clean. The restaurant is one of the best on island. The only special consideration is the low hum of noise from the restaurant which is located right next to the cottages. It’s over by the restaurant closing at about 11PM, but creates a hum of group conversation until then. The drive from Sconset to downtown takes about 15 minutes so renting a car is useful.

Reviewed on 22 Jun 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 £2,114, price is now £1,501 per person
£1,501
per person
25 Aug - 1 Sept
found 23 hours ago
Return direct flight included
Manchester (MAN) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Splendid bed and breakfast

Reviewed on 29 Apr 2026

Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was £2,582, price is now £1,875 per person
£1,875
per person
8 Sept - 15 Sept
found 11 hours ago
Return flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (713 reviews)
Everything was perfect! The beach view was spectacular. We have no complaints and would certainly go back again.

Reviewed on 23 Jun 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

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 £126 per night from 5 Jul to 6 Jul
£126
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (2,697 reviews)
"Great experience here, parking can add up, but with the discount the hotel gets you its much cheaper than it would be. Great walking distance from a variety of things to do."

Reviewed on 23 Jun 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is £155 per night from 19 Jul to 20 Jul
£155
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (2,390 reviews)
"provide shuttle bus to the town ，it's good"

Reviewed on 23 Jun 2026

Hyatt Regency Boston/Cambridge
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 £213 per night from 5 Jul to 6 Jul
£213
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (4,731 reviews)
"The room and view were absolutely amazing! This was truly one of the best hotels I have stayed at. The front desk staff was friendly, welcoming, and provided excellent service throughout our stay. The hotel offered a great variety of amenities, which made the experience even more enjoyable. The complimentary ..."

Reviewed on 23 Jun 2026

Omni Boston Hotel at the Seaport
See all 4,203 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

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University

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

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

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

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

£59
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

£27
per adult
98% of travellers recommend
History and Hauntings of Salem 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.