Are there any 5-star all-inclusive resorts in Winchester?

Our filters are the best way to narrow down what you're looking for. Select "All inclusive" and "5-star" to show the most luxurious properties in Winchester where your lodging, meals, activities and entertainment are included in the price. At these escapes, your vacation is pure extravagance from the moment you pull up to the entrance.

What are the top 5-star spa hotels in Winchester?

Pamper yourself with a spa vacation at Four Seasons Hotel Boston and let your cares drift away. Mandarin Oriental, Boston and Encore Boston Harbor are other 5-star options in Winchester where you can experience the rejuvenating and soothing powers of wellness programs and spa treatments.

Are there any 5-star vacation rentals in Winchester?

You won't find any 5-star vacation rentals in Winchester on our site, but there are a range of other highly rated properties worth checking out. Scan through our vacation rentals in Winchester to find the ideal place for your getaway.

Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA.

Winchester 5 Stars Hotels

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Our top choices for Winchester 5-star hotels

Omni Boston Hotel at the Seaport

Seaport District

Xavier

NT$7,837 total

includes taxes & fees

Jan 1 - 2026/1/2

Apartment, 2 Bedrooms | Premium bedding, down comforters, pillowtop beds, minibar

Encore Boston Harbor

Everett

Hosni

NT$7,678 total

includes taxes & fees

Jan 5 - 2026/1/6

The Langham, Boston

Downtown Boston

Caren Christina

NT$15,075 total

includes taxes & fees

Dec 19 - Dec 20

The Newbury Boston

Back Bay

Anne

NT$16,317 total

includes taxes & fees

Dec 22 - Dec 23

Four Seasons Hotel Boston

Bay Village

JUNMEI

NT$26,154 total

includes taxes & fees

Jan 5 - 2026/1/6

InterContinental Boston by IHG

Downtown Boston

Heather

NT$7,656 total

includes taxes & fees

Dec 30 - Dec 31

Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar

Boston Harbor Hotel

North End

Alisha

NT$17,266 total

includes taxes & fees

Dec 28 - Dec 29

Mandarin Oriental, Boston

Back Bay

Narek

NT$17,291 total

includes taxes & fees

Dec 25 - Dec 26

Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

Four Seasons Hotel One Dalton Street, Boston

Back Bay

Sihao

NT$18,889 total

includes taxes & fees

Dec 28 - Dec 29

The Liberty, a Marriott Luxury Collection Hotel, Boston

West End

Desiree

NT$8,137 total

includes taxes & fees

Dec 22 - Dec 23

The Ritz-Carlton, Boston

Downtown Boston

JOHN

NT$18,127 total

includes taxes & fees

Dec 21 - Dec 22

3 restaurants, breakfast, lunch, dinner served; Portuguese cuisine

Raffles Boston

Back Bay

Don

NT$20,524 total

includes taxes & fees

Dec 20 - Dec 21

XV Beacon

Beacon Hill

Jana

NT$19,452 total

includes taxes & fees

Dec 28 - Dec 29

The Bell Inn

Peabody

Ashleigh

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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.

Hilton Boston Logan Airport

One Hotel Drive Boston MA

NT$5,011

NT$5,836 total

Dec 22 - Dec 23

includes taxes & fees

8.8/10 Excellent! (3,615 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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

Top Winchester Hotel Reviews

Boston Harbor Hotel

10/10 Excellent

"The staff and room were excellent."

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$3,887

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.

Winchester 5 Stars Hotels

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