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 $125

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

$174 nightly

Feb 15 - Feb 16

Total with taxes and fees

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

Encore Boston Harbor

Everett

Troy

$259 nightly

Mar 1 - Mar 2

Total with taxes and fees

Breakfast, lunch, brunch served; Italian cuisine

The Langham, Boston

Downtown Boston

Lane

$353 nightly

Feb 7 - Feb 8

Total with taxes and fees

The Newbury Boston

Back Bay

Reggy

$467 nightly

Feb 9 - Feb 10

Total with taxes and fees

Four Seasons Hotel Boston

Bay Village

JUNMEI

$720 nightly

Feb 5 - Feb 6

Total with taxes and fees

InterContinental Boston by IHG

Downtown Boston

Annette

$218 nightly

Feb 15 - Feb 16

Total with taxes and fees

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

Boston Harbor Hotel

North End

Misty

$469 nightly

Feb 15 - Feb 16

Total with taxes and fees

Breakfast, lunch, dinner served; local and international cuisine

Mandarin Oriental, Boston

Back Bay

Narek

$436 nightly

Feb 23 - Feb 24

Total with taxes and fees

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

Four Seasons Hotel One Dalton Street, Boston

Fenway–Kenmore

brian

$485 nightly

Feb 17 - Feb 18

Total with taxes and fees

The Liberty, a Marriott Luxury Collection Hotel, Boston

West End

Karen

$240 nightly

Feb 22 - Feb 23

Total with taxes and fees

The Ritz-Carlton, Boston

Downtown Boston

Veronica

$499 nightly

Feb 5 - Feb 6

Total with taxes and fees

Raffles Boston

Back Bay

Cassandra

$472 nightly

Feb 10 - Feb 11

Total with taxes and fees

XV Beacon

Beacon Hill

Emil

$536 nightly

Feb 24 - Feb 25

Total with taxes and fees

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

$171 nightly

$200 total

Feb 24 - Feb 25

Total with taxes and 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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Top Winchester Hotel Reviews

Encore Boston Harbor

10/10 Excellent

"Very nice!!!"

Find out more about Winchester

Ready for an incredible adventure? Add even more enjoyment on your next trip to Winchester by treating yourself to the best of the best when it comes to lodging. It's an ideal pairing. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Winchester so popular in the last year. There's no reason to delay a getaway to Winchester any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Winchester are the perfect places to relax in during your next getaway. You deserve the great vacation you're dreaming about.

Book the Best Winchester 5-Star Hotels

You'll have a wonderful time at one of these 5-star hotels. Excellent service, delicious meals, and personalized service are all ready for you. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that Turkish coffee in the wee hours of the morning? A deep-tissue massage to help your cares fall away? Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

But you aren't going to spend your entire vacation in your room, of course. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winchester are waiting for you to rest up after an exciting day.

Your Getaway Starts Today

The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Select one of our Winchester 5-star hotels today and decompress in complete comfort tomorrow.

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 $125

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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