Winchester Holidays from £1,450

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Your Winchester Holiday

Book a Winchester holiday package that includes everything you need and nothing you don't. Great for nightlife, shopping and bars and pubs, consider staying in the neighbourhood of Downtown Boston. A trip to Winchester is a terrific opportunity to see the sights. Be sure to look around renowned attractions like Harvard Square, Harvard University and Bentley College. Stop dreaming and start travelling. Browse the broad range of options on Expedia today and finally put your Winchester holiday plans into gear!

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was £1,985, price is now £1,450 per person
£1,450
per person
11 Jun - 16 Jun
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.8/10 Excellent! (1,462 reviews)
Staff very friendly. Night desk clerk, Mathew, was extremely helpful and engaging. Wasn’t happy about being talked into a pre-usage amenity charge. Still not sure what it was supposed to be used for. This was a $69+ charger. Also parking a block and half away was a $50 per day. Thought a bit high.

Reviewed on 7 May 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was £2,563, price is now £1,571 per person
£1,571
per person
11 Jun - 16 Jun
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.

Reviewed on 8 May 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was £2,822, price is now £1,910 per person
£1,910
per person
11 Jun - 16 Jun
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had

Reviewed on 2 May 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was £2,081, price is now £1,462 per person
£1,462
per person
15 Jun - 22 Jun
found 10 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (77 reviews)
New hotel, very good curation of products and decor. Staff is very friendly.

Reviewed on 7 May 2026

The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Price was £2,170, price is now £1,657 per person
£1,657
per person
15 Jun - 22 Jun
found 10 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (2,042 reviews)
Loved the heated pool and how close we were to several great places to eat and see. Room was comfortable and property was kept clean.

Reviewed on 7 May 2026

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
21,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

Top hotels in Winchester

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is £243 per night from 25 May to 26 May
£243
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (4,300 reviews)
Excellent

Reviewed on 8 May 2026

Seaport Hotel 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 £109 per night from 25 May to 26 May
£109
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,602 reviews)
The location was perfect. Super fun hotel. Would absolutely stay here again

Reviewed on 8 May 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is £203 per night from 25 May to 26 May
£203
25 May - 26 May
includes taxes & fees
9.2/10 Wonderful! (4,641 reviews)
Great location. Nice modern room.

Reviewed on 8 May 2026

Omni Boston Hotel at the Seaport
See all 4,207 properties in Winchester
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 Winchester

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

£62
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

£25
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Winchester

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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.