A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Winchester 5 Stars Hotels

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Our top choices for Winchester 5-star hotels

Breakfast, lunch and brunch served

The Langham, Boston

The Langham, Boston
5.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (1,005 reviews)
"Well located and very well maintained property."
United States
mohan
The price is NT$14,646
NT$17,055 total
includes taxes & fees
Aug 2 - Aug 3
The Langham, Boston
4 restaurants; breakfast, lunch, and dinner served

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,813 reviews)
"Great location and rooms"
United States
Aimee
The price is NT$7,185
NT$9,679 total
includes taxes & fees
Jul 26 - Jul 27
Omni Boston Hotel at the Seaport
Apartment, 2 Bedrooms | Premium bedding, down comforters, pillowtop beds, minibar

Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,948 reviews)
"It was an incredible place to stay, can’t wait to go back!"
United States
Patricia
The price is NT$7,127
NT$7,960 total
includes taxes & fees
Aug 2 - Aug 3
Encore Boston Harbor
3 restaurants; breakfast, lunch, dinner, and brunch served

The Charles Hotel

The Charles Hotel
5.0 star property
West Cambridge
9.4 out of 10, Exceptional, (1,010 reviews)
"Great location"
United States
Carmen
The price is NT$10,338
NT$11,987 total
includes taxes & fees
Aug 12 - Aug 13
The Charles Hotel
Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar

Boston Harbor Hotel

Boston Harbor Hotel
5.0 star property
North End
9.8 out of 10, Exceptional, (1,011 reviews)
"Everything was great 👍"
United States
Peter
The price is NT$16,717
NT$19,485 total
includes taxes & fees
Aug 2 - Aug 3
Boston Harbor Hotel
Lunch and dinner served

The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (684 reviews)
"Great location, staff and service."
United States
Gino
The price is NT$17,704
NT$22,303 total
includes taxes & fees
Jul 28 - Jul 29
The Newbury Boston
Property amenity

The Liberty, a Marriott Luxury Collection Hotel, Boston

The Liberty, a Marriott Luxury Collection Hotel, Boston
5.0 star property
West End
8.8 out of 10, Excellent, (1,012 reviews)
"Great place in a great location! Staff was great"
United States
Donald
The price is NT$9,549
NT$12,057 total
includes taxes & fees
Jul 26 - Jul 27
The Liberty, a Marriott Luxury Collection Hotel, Boston
Exterior

InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1,159 reviews)
"They let us check in early after a red eye flight which made our whole trip"
United States
Brian
The price is NT$7,120
NT$9,753 total
includes taxes & fees
Jul 26 - Jul 27
InterContinental Boston by IHG
Breakfast, lunch and dinner served

Mandarin Oriental, Boston

Mandarin Oriental, Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (434 reviews)
"The staff were aware of our celebration and helped us accomplish our goals in celebrating. They were kind and thoughtful. Everything was lovely, the decor, the furniture, the space, the amenities."
United States
Christina
The price is NT$18,026
NT$20,991 total
includes taxes & fees
Aug 2 - Aug 3
Mandarin Oriental, Boston
Terrace/patio

Four Seasons Hotel Boston

Four Seasons Hotel Boston
5.0 star property
Bay Village
9.4 out of 10, Exceptional, (474 reviews)
"The best hotel in Boston "
United States
Madina
The price is NT$26,073
NT$30,362 total
includes taxes & fees
Aug 2 - Aug 3
Four Seasons Hotel Boston
Reception

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
5.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (471 reviews)
"Great hotel, great food and friendly staff "
United States
Oswaldo
The price is NT$20,247
NT$23,578 total
includes taxes & fees
Aug 2 - Aug 3
The Ritz-Carlton, Boston
Indoor pool

Raffles Boston

Raffles Boston
5.0 star property
Back Bay
9.6 out of 10, Exceptional, (280 reviews)
"This hotel was so beautiful and exceptional "
United States
Darlene
The price is NT$20,858
NT$24,290 total
includes taxes & fees
Aug 9 - Aug 10
Raffles Boston
Exterior

XV Beacon

XV Beacon
5.0 star property
Beacon Hill
9.4 out of 10, Exceptional, (395 reviews)
"The location was fantastic for all things Boston! It was a very walkable location and such a comfortable room and a very friendly staff that was very helpful."
United States
Robin
The price is NT$17,237
NT$20,073 total
includes taxes & fees
Aug 9 - Aug 10
XV Beacon
Honeymoon Room | In-room dining

The Bell Inn

The Bell Inn
5.0 star property
Peabody
9.4 out of 10, Exceptional, (258 reviews)
"Amazing and beautiful place to stay with everything close by 10/10 recommend"
United States
Carey
The price is NT$4,879
NT$5,449 total
includes taxes & fees
Jul 13 - Jul 14
The Bell Inn
Lounge

Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
5.0 star property
Inner Belt
10.0 out of 10, Exceptional, (3 reviews)
"I was staying in the Boston area for work and this was the perfect place to stay. Lots of room and easy to get to and the staff were very responsive and helpful. I would highly recommend!"
Canada
Peter
Luxury Apartments by Hyatus Boston Somerville
Billiards

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
5.0 star property
Everett
9.2 out of 10, Wonderful, (5 reviews)
"Family trip for competition travel and the property was exactly what we needed. Clean room, comfortable beds, and a peaceful environment after long tournament days. Staff was professional and welcoming, and the location made everything easier for our family. Traveling with kids can be stressful, but this stay helped us reset and stay focused. Would definitely stay again. "
United States
Trenthony
Luxury Apartments by Hyatus at Boston Everett
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester.
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
The price is NT$6,406 per night from Jul 26 to Jul 27
NT$6,406
NT$8,557 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,574 reviews)
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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.

Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

See all hotels in Winchester
A historic building with a clock tower, red brick walls, and a green roof.

Top Winchester Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Everyone was friendly and professional! The Omni is extremely clean! And the food options are wonderful"
Dominique 2-night trip
Posted 1 hour ago
Omni Boston Hotel at the Seaport

Frequently asked questions

What are the best 5-star hotels in Winchester?
Get set for 5-star indulgence at Encore Boston Harbor, The Liberty, a Marriott Luxury Collection Hotel, Boston or XV Beacon. These are among the top-rated escapes in Winchester according to Expedia traveler reviews. Pick one and get a taste of the good life!
How much does it cost to stay in a 5-star hotel in Winchester?
The amount you pay for a 5-star hotel in Winchester depends on things like when you plan to go and the length of your trip. Our top tip for scoring the best deal? Use our pricing filters to check out the available hotels for your preferred dates.

  • Search for the lowest price per night from NT$6,605

What makes a hotel 5 stars in Winchester?
Flawless guest service is the defining feature of every 5-star hotel in Winchester. From the second you arrive, staff attend to your every need, whether offering luggage assistance and storage or providing in-room beauty treatments. What's more, hotels have to feature upscale amenities to meet the standard for a 5-star rating. These can include luxury bathrooms, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.

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