A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Winchester 5 Stars Hotels

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Check availability on Winchester 5 Star Hotels

Tonight
Aug 27 - Aug 28
Tomorrow
Aug 28 - Aug 29
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Winchester 5-star hotels

A modern rooftop lounge with seating and tables, a cityscape view, and a decorative wall mural.
A modern hotel lobby with a bar area, seating arrangements, and a fireplace.
A hotel room with a large bed, a desk, a chair, and a view of a cityscape through a large window.

1. Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
Seaport District
United States
Sandra Burns
NT$6,988
NT$9,437 total
includes taxes & fees
Aug 30 - Aug 31
Omni Boston Hotel at the Seaport
A modern bedroom with a large bed, a nightstand, a lamp, a potted plant, and a view of a cityscape at night.
A modern hotel room with a large window offering a city view, a flat-screen TV, a sofa, a coffee table, and a decorative painting.
A hotel room with a large city view, a round dining table, and a sofa.
A large hotel with a curved facade and the name "Encore" illuminated on the top.

2. Encore Boston Harbor

Encore Boston Harbor
Everett
United States
Melissa
NT$9,127
NT$10,195 total
includes taxes & fees
Sep 21 - Sep 22
Encore Boston Harbor
A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
A large, classical building with multiple windows and a prominent entrance.
An outdoor cafe with tables and chairs, a stone facade, and flags.
A grand hall with ornate ceiling and large windows.

3. The Langham, Boston

The Langham, Boston
Downtown Boston
United States
Lawrence
NT$16,736
NT$19,490 total
includes taxes & fees
Aug 28 - Aug 29
The Langham, Boston
A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
A cityscape with modern high-rise buildings, a central roundabout, and a mix of commercial and residential structures.
A hotel room with a large bed, a TV, a desk, and a view of the sea.
A banquet hall with tables set for a formal event, featuring floral centerpieces and chandeliers.

4. Boston Harbor Hotel

Boston Harbor Hotel
North End
United States
Carl
NT$21,072
NT$24,556 total
includes taxes & fees
Aug 30 - Aug 31
Boston Harbor Hotel
The Charles Hotel with outdoor seating and a garden area.
A staircase with a modern design, featuring a combination of brick and wood elements, and a metal railing.
A restaurant with a wooden table centerpiece, orchid plants, and a sign for Henrietta's Table.
A hotel with a brick facade, large windows, and a prominent entrance with a glass door.

5. The Charles Hotel

The Charles Hotel
West Cambridge
United States
Daniel
NT$11,376
NT$13,190 total
includes taxes & fees
Aug 30 - Aug 31
The Charles Hotel
A modern building with a glass facade, a waterfront view, and a dock area with boats.
A table with a variety of food and drink items, including a bottle of champagne, glasses, and macarons, set against a cityscape view.
A spacious, well-lit event space with a reflective floor, large windows, and elegant floral centerpieces.
A modern lobby with a central seating area, a reception desk, and a distinctive geometric light fixture.

6. InterContinental Boston by IHG

InterContinental Boston by IHG
Downtown Boston
United States
Donna
NT$8,002
NT$10,766 total
includes taxes & fees
Aug 30 - Aug 31
InterContinental Boston by IHG
A rooftop dining area with a round table set for two, surrounded by plush seating and potted plants.
A bar area with seating, a fireplace, and bookshelves.
A park with a lamp post, a bridge, and buildings in the background.
A spacious living room with a large sofa, two armchairs, a coffee table, and a dining area with a table and chairs.

7. The Newbury Boston

The Newbury Boston
Back Bay
United States
Sandra
NT$18,792
NT$23,551 total
includes taxes & fees
Aug 29 - Aug 30
The Newbury Boston
A courtyard with brick walls, outdoor seating, and potted plants.
A modern indoor pool area with large windows, comfortable seating, and a city view.
A bar area with a long counter, multiple hanging lamps, and a variety of bottles and glasses.
A grand lobby with a checkered floor, green walls, and classic furniture.

8. Four Seasons Hotel Boston

Four Seasons Hotel Boston
Bay Village
United States
Roxane
NT$25,822
NT$30,070 total
includes taxes & fees
Aug 30 - Aug 31
Four Seasons Hotel Boston
A modern indoor pool area with a large window, a woman in a swimsuit, and two lounge chairs.
A modern hotel room with a curved seating area, a coffee table, and a view of the cityscape through large windows.
A hotel room with a large window offering a city view, a bed, a chair, and a small table with a tray.
A modern bathroom with a large bathtub, a glass shower enclosure, and a view of a cityscape through large windows.

9. Four Seasons Hotel One Dalton Street, Boston

Four Seasons Hotel One Dalton Street, Boston
Fenway–Kenmore
United States
Omar
NT$21,200
NT$24,687 total
includes taxes & fees
Sep 2 - Sep 3
Four Seasons Hotel One Dalton Street, Boston
A multi-level atrium with a central bar, seating areas, and a staircase.
A multi-level interior with hanging greenery and a bar area.
A spacious lobby with a high ceiling, a large chandelier, and a seating area with leather chairs.
A cobblestone street lined with brick buildings, each with a door and windows, and a street lamp on the right.

10. The Liberty, a Marriott Luxury Collection Hotel, Boston

The Liberty, a Marriott Luxury Collection Hotel, Boston
West End
United States
Larry
NT$8,866
NT$11,252 total
includes taxes & fees
Aug 30 - Aug 31
The Liberty, a Marriott Luxury Collection Hotel, Boston
A modern bar area with multiple seating options, a well-stocked bar counter, and a distinctive ceiling design.
A modern lounge with two sofas, a fireplace, and a unique ceiling chandelier.
A lobby with a central round table, potted plants, and artwork on the walls.
A multi-story building with a central entrance, American and another flag, parked cars, and a tree with white blossoms.

11. Mandarin Oriental, Boston

Mandarin Oriental, Boston
Back Bay
United States
Leslie
NT$21,338
NT$24,848 total
includes taxes & fees
Sep 6 - Sep 7
Mandarin Oriental, Boston
A modern lobby with a staircase, seating area, and large windows offering city views.
A rooftop terrace with outdoor seating, ambient lighting, and a city view at dusk.
A high-rise hotel lobby with large windows, a chandelier, and seating areas.

12. Raffles Boston

Raffles Boston
Back Bay
United States
Robinette
NT$20,785
NT$24,204 total
includes taxes & fees
Aug 30 - Aug 31
Raffles Boston
A spacious lobby with a central seating area, a large chandelier, and a fireplace.
A luxurious living room with a fireplace, leather sofas, and a patterned carpet.
A bar area with multiple shelves of bottles and glasses, bar stools, and a warm, well-lit ambiance.
A modern hotel bathroom with a marble vanity, a large bathtub, and a city view through an open door.

13. The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
Downtown Boston
United States
Maxim
NT$20,017
NT$23,310 total
includes taxes & fees
Aug 29 - Aug 30
The Ritz-Carlton, Boston
A hotel with a classic facade, large windows, and a prominent entrance.
A modern living room with a fireplace, two armchairs, a coffee table, and a zebra-patterned rug.
A hotel room with a large bed, a sofa, a desk, a television, and a fireplace.
A rooftop terrace with a table, chairs, and a view of the city skyline.

14. XV Beacon

XV Beacon
Beacon Hill
United States
Robin
NT$17,071
NT$19,879 total
includes taxes & fees
Aug 31 - Sep 1
XV Beacon
A spacious room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.
A modern kitchen with white cabinets, stainless steel appliances, and a tiled floor.
A room with a white wall-mounted lamp, a window with curtains, a sofa, and a patterned chair.
A building with a sign reading "THE CELLAR" and a wooden gate.

15. The Bell Inn

The Bell Inn
Peabody
United States
Joseph A
NT$4,502
NT$5,028 total
includes taxes & fees
Sep 2 - Sep 3
The Bell Inn
A modern interior with a pool table, green seating, and large windows offering a view of the outside.
A spacious lobby with a modern design, featuring a curved seating area, a central fire feature, and a mix of seating options including sofas and chairs.
An aerial view of a hotel courtyard with a swimming pool, outdoor seating, and greenery.
A spacious lobby with large windows, a central seating area with sofas and chairs, and a modern design with a large screen on the wall.

16. Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
Everett
United States
Trenthony
Luxury Apartments by Hyatus at Boston Everett
A modern kitchen with a large island, pendant lighting, and a view of the outdoors.
A modern kitchen with a central island, bar stools, and a fireplace.
A modern living room with a green sofa, a round coffee table, and a bookshelf.
A spacious dining area with a large wooden table, six wooden stools, and a modern chandelier.

17. Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
Inner Belt
Canada
Peter
Luxury Apartments by Hyatus Boston Somerville
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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
NT$6,027
NT$8,106 total
Sep 6 - Sep 7
includes taxes & fees
9.6/10 Exceptional! (4,869 reviews)
Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

50 Park Plaza Boston MA
NT$5,715
NT$7,952 total
Sep 6 - Sep 7
includes taxes & fees
Hilton Boston Park Plaza
The Dagny Boston

The Dagny Boston

89 Broad Street Boston MA
NT$7,300
NT$9,615 total
Aug 30 - Aug 31
includes taxes & fees
9.6/10 Exceptional! (7,431 reviews)
The Dagny Boston
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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
A historic building with a clock tower, red brick walls, and a green roof.

Top Winchester Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in Winchester?
Get set for 5-star indulgence at Encore Boston Harbor, The Liberty, a Marriott Luxury Collection Hotel, Boston or XV Beacon. These are among the top-rated escapes in Winchester according to Expedia traveler reviews. Pick one and get a taste of the good life!
How much does it cost to stay in a 5-star hotel in Winchester?
The amount you pay for a 5-star hotel in Winchester depends on things like when you plan to go and the length of your trip. Our top tip for scoring the best deal? Use our pricing filters to check out the available hotels for your preferred dates.
  • Search for the lowest price per night from NT$7,952
What makes a hotel 5 stars in Winchester?
Flawless guest service is the defining feature of every 5-star hotel in Winchester. From the second you arrive, staff attend to your every need, whether offering luggage assistance and storage or providing in-room beauty treatments. What's more, hotels have to feature upscale amenities to meet the standard for a 5-star rating. These can include luxury bathrooms, saunas or spas, pools, gastronomic restaurants and knowledgeable concierge.

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