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

Find a luxury getaway that includes your room, meals, activities and entertainment in Winchester with our handy filters. Search for resorts rated 5 stars and click on the "All inclusive" filter. Double-check what's included in the price. This way, you can take full advantage of all the perks on offer when you arrive.

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

Recharge your batteries with luxurious massages and other revitalizing treatments at Four Seasons Hotel Boston . It's one of Winchester's top 5-star spa properties. Mandarin Oriental Boston and Encore Boston Harbor also blend upscale accommodations with wellness programs and therapies.

Are there any 5-star vacation rentals in Winchester?

Although you won't find any 5-star vacation rentals in Winchester on our site, we have a range of properties that promise a fantastic getaway. Discover one that matches your needs by searching our vacation rentals in Winchester .

The Best 5 Star Hotels in Winchester, MA from SAR 507

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

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Our top choices for Winchester 5-star hotels

Premium bedding, down comforters, pillowtop beds, in-room safe

Omni Boston Hotel at the Seaport

Seaport District

Suzanne

SAR 778 total

includes taxes & fees

8 Feb - 9 Feb

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

Encore Boston Harbor

Everett

Troy

SAR 975 total

includes taxes & fees

26 Feb - 27 Feb

Breakfast, lunch, brunch served; Italian cuisine

The Langham, Boston

Downtown Boston

Lane

SAR 1,638 total

includes taxes & fees

6 Feb - 7 Feb

The Newbury Boston

Back Bay

Reggy

SAR 1,962 total

includes taxes & fees

16 Feb - 17 Feb

Four Seasons Hotel Boston

Bay Village

JUNMEI

SAR 3,144 total

includes taxes & fees

4 Feb - 5 Feb

InterContinental Boston by IHG

Downtown Boston

Annette

SAR 1,002 total

includes taxes & fees

16 Feb - 17 Feb

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

Boston Harbor Hotel

North End

Misty

SAR 1,912 total

includes taxes & fees

17 Feb - 18 Feb

Breakfast, lunch, dinner served; local and international cuisine

Mandarin Oriental, Boston

Back Bay

Narek

SAR 1,792 total

includes taxes & fees

9 Feb - 10 Feb

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

Four Seasons Hotel One Dalton Street, Boston

Fenway–Kenmore

brian

SAR 2,118 total

includes taxes & fees

25 Feb - 26 Feb

The Liberty, a Marriott Luxury Collection Hotel, Boston

West End

Karen

SAR 1,048 total

includes taxes & fees

22 Feb - 23 Feb

The Ritz-Carlton, Boston

Downtown Boston

Veronica

SAR 2,179 total

includes taxes & fees

6 Feb - 7 Feb

Raffles Boston

Back Bay

Cassandra

SAR 1,939 total

includes taxes & fees

9 Feb - 10 Feb

XV Beacon

Beacon Hill

Emil

SAR 2,339 total

includes taxes & fees

16 Feb - 17 Feb

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

SAR 643

SAR 749 total

23 Feb - 24 Feb

includes taxes & fees

8.8/10 Excellent! (3,661 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.

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Frequently asked questions

What are the best 5-star hotels in Winchester?

According to Expedia guest reviews, Encore Boston Harbor, The Liberty, a Marriott Luxury Collection Hotel, Boston and XV Beacon are among the most popular 5-star hotels in Winchester. Offering best-in-class amenities and unparalleled service, you can expect an opulent and memorable stay.

How much does it cost to stay in a 5-star hotel in Winchester?

You can find various pricing options for 5-star hotels in Winchester on Expedia. The amount you pay will depend on your travel dates, length of stay and other factors. Compare all of the available accommodations for your preferred dates and make use of our pricing and other filters to score the perfect high-end stay.

Search for the lowest price per night from SAR 507

What makes a hotel 5 stars in Winchester?

Exemplary guest service is at the heart of every 5-star hotel in Winchester. From the moment you arrive, staff cater to your every need, whether recommending activities and tours or providing a nightly turn-down service. Additionally, hotels have to feature top-rate amenities to qualify for a 5-star rating. These can include luxury baths, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.

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