Find 5 Star Hotels in Winchester, MA from $125

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Our top choices for Winchester 5-star hotels

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,446 reviews)
"Beautiful hotel!"
United States
Suzanne
$174 nightly
The price is $203
Feb 15 - Feb 16
Total with taxes and fees
Omni Boston Hotel at the Seaport

Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,553 reviews)
"Great place to stay "
United States
Troy
$259 nightly
The price is $290
Mar 1 - Mar 2
Total with taxes and fees
Encore Boston Harbor

The Langham, Boston

The Langham, Boston
5.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (1,008 reviews)
"Very nice hotel with excellent staff."
United States
Lane
$353 nightly
The price is $410
Feb 7 - Feb 8
Total with taxes and fees
The Langham, Boston

The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.2 out of 10, Wonderful, (579 reviews)
"Friendliness staffs, location, and amenities."
United States
Reggy
$467 nightly
The price is $544
Feb 9 - Feb 10
Total with taxes and fees
The Newbury Boston

Four Seasons Hotel Boston

Four Seasons Hotel Boston
5.0 star property
Bay Village
9.4 out of 10, Exceptional, (459 reviews)
"Very classic hotel and nice food in the restaurant "
Canada
JUNMEI
$720 nightly
The price is $838
Feb 5 - Feb 6
Total with taxes and fees
Four Seasons Hotel Boston

InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1,067 reviews)
"Terrific stay & absolutely wonderful staff, food, etc."
United States
Annette
$218 nightly
The price is $254
Feb 15 - Feb 16
Total with taxes and fees
InterContinental Boston by IHG

Boston Harbor Hotel

Boston Harbor Hotel
5.0 star property
North End
9.8 out of 10, Exceptional, (1,003 reviews)
"Amazing staff, decent room & nice location!"
United States
Misty
$469 nightly
The price is $546
Feb 15 - Feb 16
Total with taxes and fees
Boston Harbor Hotel

Mandarin Oriental, Boston

Mandarin Oriental, Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (393 reviews)
"Excellent service"
United States
Narek
$436 nightly
The price is $508
Feb 23 - Feb 24
Total with taxes and fees
Mandarin Oriental, Boston

Four Seasons Hotel One Dalton Street, Boston

Four Seasons Hotel One Dalton Street, Boston
5.0 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (383 reviews)
"Great place too stay "
United States
brian
$485 nightly
The price is $565
Feb 17 - Feb 18
Total with taxes and fees
Four Seasons Hotel One Dalton Street, Boston

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, (1,003 reviews)
"Fantastic hotel in every way "
United States
Karen
$240 nightly
The price is $279
Feb 22 - Feb 23
Total with taxes and fees
The Liberty, a Marriott Luxury Collection Hotel, Boston

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
5.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (429 reviews)
"We had a great stay!"
United States
Veronica
$499 nightly
The price is $581
Feb 5 - Feb 6
Total with taxes and fees
The Ritz-Carlton, Boston

Raffles Boston

Raffles Boston
5.0 star property
Back Bay
9.6 out of 10, Exceptional, (222 reviews)
"Attentive Staff, gorgeous property, clean rooms"
United States
Cassandra
$472 nightly
The price is $550
Feb 10 - Feb 11
Total with taxes and fees
Raffles Boston

XV Beacon

XV Beacon
5.0 star property
Beacon Hill
9.4 out of 10, Exceptional, (385 reviews)
"Great Staff, very nice room. Ideal location for exploring Boston history and access to the T"
United States
Emil
$536 nightly
The price is $624
Feb 24 - Feb 25
Total with taxes and fees
XV Beacon

The Bell Inn

The Bell Inn
5.0 star property
Peabody
9.4 out of 10, Exceptional, (231 reviews)
"Terrific food in the Tavern! "
United States
Ashleigh
The Bell Inn
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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.

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

Top Winchester Hotel Reviews

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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