Find 5 Star Hotels in Winchester, MA from $182

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Check availability on Winchester 5 Star Hotels

Tonight
Mar 7 - Mar 8
Tomorrow
Mar 8 - Mar 9
Next weekend
Mar 13 - Mar 15
In two weeks
Mar 20 - Mar 22

Our top choices for Winchester 5-star hotels

Front of property

Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,597 reviews)
"Great place to stay "
United States
Troy
$235 nightly
The price is $263
Mar 30 - Mar 31
Total with taxes and fees
Encore Boston Harbor
Breakfast, lunch, brunch served; Italian cuisine

The Langham, Boston

The Langham, Boston
5.0 star property
Downtown Boston
9.6 out of 10, Exceptional, (1,004 reviews)
"Very nice hotel with excellent staff."
United States
Lane
$395 nightly
The price is $460
Mar 20 - Mar 21
Total with taxes and fees
The Langham, Boston
Restaurant

The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.2 out of 10, Wonderful, (590 reviews)
"Friendliness staffs, location, and amenities."
United States
Reggy
$494 nightly
The price is $575
Mar 11 - Mar 12
Total with taxes and fees
The Newbury Boston
Exterior

InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1,096 reviews)
"Terrific stay & absolutely wonderful staff, food, etc."
United States
Annette
$241 nightly
The price is $281
Mar 22 - Mar 23
Total with taxes and fees
InterContinental Boston by IHG
Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar

Boston Harbor Hotel

Boston Harbor Hotel
5.0 star property
North End
9.8 out of 10, Exceptional, (1,002 reviews)
"Amazing staff, decent room & nice location!"
United States
Misty
$535 nightly
The price is $622
Mar 8 - Mar 9
Total with taxes and fees
Boston Harbor Hotel
Breakfast, lunch, dinner served; local and international cuisine

Mandarin Oriental, Boston

Mandarin Oriental, Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (401 reviews)
"Excellent service"
United States
Narek
$580 nightly
The price is $675
Mar 29 - Mar 30
Total with taxes and fees
Mandarin Oriental, Boston
Property amenity

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, (1,008 reviews)
"Fantastic hotel in every way "
United States
Karen
$254 nightly
The price is $296
Mar 22 - Mar 23
Total with taxes and fees
The Liberty, a Marriott Luxury Collection Hotel, Boston
Reception

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
5.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (437 reviews)
"We had a great stay!"
United States
Veronica
$599 nightly
The price is $698
Mar 19 - Mar 20
Total with taxes and fees
The Ritz-Carlton, Boston
Terrace/patio

Four Seasons Hotel Boston

Four Seasons Hotel Boston
5.0 star property
Bay Village
9.4 out of 10, Exceptional, (463 reviews)
"Very classic hotel and nice food in the restaurant "
Canada
JUNMEI
$765 nightly
The price is $891
Mar 31 - Apr 1
Total with taxes and fees
Four Seasons Hotel Boston
Indoor pool

Raffles Boston

Raffles Boston
5.0 star property
Back Bay
9.6 out of 10, Exceptional, (237 reviews)
"Attentive Staff, gorgeous property, clean rooms"
United States
Cassandra
$596 nightly
The price is $694
Mar 15 - Mar 16
Total with taxes and fees
Raffles Boston
Rooftop terrace

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
Mar 8 - Mar 9
Total with taxes and fees
XV Beacon
Billiards

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
5.0 star property
Everett
10.0 out of 10, Exceptional, (1 review)
"Honestly this was one of the best furnished apartments I’ve ever stayed in, and I travel a lot for work. My partner and I came with another couple and we all kept saying how we wished we had booked a few extra nights. The place was super clean, modern, and honestly way bigger than we expected lol. First night we accidentally got the wrong door code but the host fixed it in like two minutes which was amazing. The living room became our hangout spot every evening and we even cooked dinner together...
United States
Yitzy
Luxury Apartments by Hyatus at Boston Everett
Lounge

Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
5.0 star property
Inner Belt
10.0 out of 10, Exceptional, (2 reviews)
"I was staying in the Boston area for work and this was the perfect place to stay. Lots of room and easy to get to and the staff were very responsive and helpful. I would highly recommend!"
Canada
Peter
Luxury Apartments by Hyatus Boston Somerville
Honeymoon Room | In-room dining

The Bell Inn

The Bell Inn
5.0 star property
Peabody
9.4 out of 10, Exceptional, (231 reviews)
"Lovely stay"
United States
Laura
The Bell Inn
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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.
Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
$157 nightly
The price is $182 total per night from Mar 8 to Mar 9
$182 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (4,038 reviews)
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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
Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA.

Top Winchester Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Beautiful resort and the rooms are luxurious."
Julia 1-night trip
Posted 8 hours ago
Encore Boston Harbor

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 $182

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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