Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.

5 Stars Hotels in Winchester

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Check availability on Winchester 5 Star Hotels

Our top choices for Winchester 5-star hotels

Breakfast, lunch and brunch served

The Langham, Boston

The Langham, Boston
5.0 star property
Downtown Boston
9.8 out of 10, Exceptional, (1,014 reviews)
"Well located and very well maintained property."
United States
mohan
The price is ฿19,477
฿22,681 total
includes taxes & fees
20 Jun - 21 Jun
The Langham, Boston
4 restaurants; breakfast, lunch and dinner served

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,735 reviews)
"The hotel was fantastic."
United States
Wilson
The price is ฿6,259
฿8,623 total
includes taxes & fees
2 Jul - 3 Jul
Omni Boston Hotel at the Seaport
Apartment, 2 Bedrooms | Premium bedding, down duvets, pillow-top beds, minibar

Encore Boston Harbor

Encore Boston Harbor
5.0 star property
Everett
9.6 out of 10, Exceptional, (3,868 reviews)
"It was an incredible place to stay, can’t wait to go back!"
United States
Patricia
The price is ฿15,025
฿16,783 total
includes taxes & fees
30 Jun - 1 Jul
Encore Boston Harbor
Lunch and dinner served

The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (661 reviews)
"We loved it! Beautiful rooms and Contessa was delicious :)"
United States
Jeanne
The price is ฿19,859
฿24,842 total
includes taxes & fees
6 Jul - 7 Jul
The Newbury Boston
Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillow-top beds, minibar

Boston Harbor Hotel

Boston Harbor Hotel
5.0 star property
North End
9.8 out of 10, Exceptional, (1,007 reviews)
"The best service of any hotel hands down!!!"
United States
Carlton
The price is ฿19,160
฿22,330 total
includes taxes & fees
6 Jul - 7 Jul
Boston Harbor Hotel
Exterior

InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1,130 reviews)
"Well designed. Spacious room. Great front desk staff and concierge."
Canada
Peter
The price is ฿8,216
฿11,055 total
includes taxes & fees
1 Jul - 2 Jul
InterContinental Boston by IHG
Suite (Charles) | Deep-soaking bathtub

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, (416 reviews)
"wonderful stay "
United States
Heather
The price is ฿21,604
฿25,158 total
includes taxes & fees
6 Jul - 7 Jul
Four Seasons Hotel One Dalton Street, 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, (1,012 reviews)
"Best hotel, best staff ever."
United States
Alexandria
The price is ฿10,459
฿13,132 total
includes taxes & fees
21 Jun - 22 Jun
The Liberty, a Marriott Luxury Collection Hotel, Boston
Breakfast, lunch and dinner served

Mandarin Oriental, Boston

Mandarin Oriental, Boston
5.0 star property
Back Bay
9.4 out of 10, Exceptional, (428 reviews)
"great stay "
United States
Heather
The price is ฿23,527
฿27,397 total
includes taxes & fees
13 Jul - 14 Jul
Mandarin Oriental, Boston
Indoor pool

Raffles Boston

Raffles Boston
5.0 star property
Back Bay
9.6 out of 10, Exceptional, (273 reviews)
"This hotel was so beautiful and exceptional "
United States
Darlene
The price is ฿22,652
฿26,378 total
includes taxes & fees
6 Jul - 7 Jul
Raffles Boston
Reception

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
5.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (466 reviews)
"Great hotel, great food and friendly staff "
United States
Oswaldo
The price is ฿22,881
฿26,645 total
includes taxes & fees
1 Jul - 2 Jul
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, (474 reviews)
"Very classic hotel and nice food in the restaurant "
Canada
JUNMEI
Four Seasons Hotel Boston
Exterior

XV Beacon

XV Beacon
5.0 star property
Beacon Hill
9.4 out of 10, Exceptional, (392 reviews)
"The location was fantastic for all things Boston! It was a very walkable location and such a comfortable room and a very friendly staff that was very helpful."
United States
Robin
The price is ฿17,529
฿20,413 total
includes taxes & fees
1 Jul - 2 Jul
XV Beacon
Honeymoon Room | In-room dining

The Bell Inn

The Bell Inn
5.0 star property
Peabody
9.4 out of 10, Exceptional, (242 reviews)
"Clean room, staff were very friendly and helpful."
United States
Ryan
The price is ฿4,961
฿5,542 total
includes taxes & fees
16 Jul - 17 Jul
The Bell Inn
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, (3 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
Billiards

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
5.0 star property
Everett
9.2 out of 10, Wonderful, (5 reviews)
"Family trip for competition travel and the property was exactly what we needed. Clean room, comfortable beds, and a peaceful environment after long tournament days. Staff was professional and welcoming, and the location made everything easier for our family. Traveling with kids can be stressful, but this stay helped us reset and stay focused. Would definitely stay again. "
United States
Trenthony
Luxury Apartments by Hyatus at Boston Everett
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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

Hilton Boston Logan Airport

One Hotel Drive Boston MA
The price is ฿7,294 per night from 30 Jun to 1 Jul
฿7,294
฿8,494 total
30 Jun - 1 Jul
includes taxes & fees
9/10 Wonderful! (3,842 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

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Very nice hotel, views and room were excellent. Conveniently located to walk to restaurants and some docks."
Della 1-night trip
Posted 3 hours ago
Omni Boston Hotel at the Seaport

Frequently asked questions

What are the best 5-star hotels in Winchester?
Encore Boston Harbour, The Liberty, a Marriott Luxury Collection Hotel, Boston and XV Beacon are some of the top 5-star hotels in Winchester, according to our customer reviews. These plush hotels rate highly for things like their location, amenities and guest services. Select your favourite and enjoy the best of it all.
How much does it cost to stay in a 5-star hotel in Winchester?
How much you pay for a 5-star hotel in Winchester can vary depending on the time of year you travel and how long you plan to be away, among a range of factors. Use our price per night filter and other search tools to find the best rate on a high-end getaway.

  • Search for the lowest price per night from ฿8,323

What makes a hotel 5 stars in Winchester?
In Winchester, a hotel is required to offer a certain number of high-end amenities to earn a 5-star rating. These can include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their exceptional service. You can look forward to things like concierge services, nightly turn-down services and in-room massage. Some may also offer additional touches such as welcome gifts.