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 .

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

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Compare Winchester 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Omni Boston Hotel at the Seaport

Seaport District

Marlene

SAR 761 total

includes taxes & fees

18 Dec - 19 Dec

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

Encore Boston Harbor

Everett

Jennifer

SAR 783 total

includes taxes & fees

1 Dec - 2 Dec

The Langham, Boston

Downtown Boston

Patricia

SAR 1,594 total

includes taxes & fees

30 Nov - 1 Dec

The Newbury Boston

Back Bay

Anne

SAR 2,119 total

includes taxes & fees

14 Dec - 15 Dec

Four Seasons Hotel Boston

Bay Village

Sharon Mary

SAR 3,276 total

includes taxes & fees

29 Nov - 30 Nov

InterContinental Boston by IHG

Downtown Boston

Dana

SAR 731 total

includes taxes & fees

22 Dec - 23 Dec

Suite, Multiple Beds (John Adams Presidential Suite) | 1 bedroom, Frette Italian sheets, premium bedding, pillowtop beds

Boston Harbor Hotel

North End

Brian

SAR 1,539 total

includes taxes & fees

30 Nov - 1 Dec

Mandarin Oriental, Boston

Back Bay

Niki

SAR 2,013 total

includes taxes & fees

14 Dec - 15 Dec

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

Four Seasons Hotel One Dalton Street, Boston

Back Bay

Sihao

SAR 2,424 total

includes taxes & fees

28 Dec - 29 Dec

The Liberty, a Marriott Luxury Collection Hotel, Boston

West End

Chace

SAR 978 total

includes taxes & fees

28 Dec - 29 Dec

The Ritz-Carlton, Boston

Downtown Boston

JOHN

SAR 2,180 total

includes taxes & fees

30 Nov - 1 Dec

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

Raffles Boston

Back Bay

Don

SAR 2,599 total

includes taxes & fees

29 Nov - 30 Nov

XV Beacon

Beacon Hill

Jana

SAR 2,339 total

includes taxes & fees

13 Dec - 14 Dec

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 581

SAR 677 total

23 Dec - 24 Dec

includes taxes & fees

8.8/10 Excellent! (3,583 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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Top Winchester Hotel Reviews

The Langham, Boston

10/10 Excellent

"Clean room and staff were very friendly and the breakfast was amazing . This is a gorgeous hotel and we will definitely be staying here on our next visit . "

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.

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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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