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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester 5 Star Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Winchester 5-star hotels

A modern restaurant with round tables and chairs, large windows with a city view, and a geometric patterned floor.
A modern living room with a city view, featuring a sofa, armchairs, a coffee table, and a dining area.
A hotel room with a large bed, a desk, a chair, and a view of a cityscape through a large window.
A modern hotel lobby with a bar area, seating arrangements, and a fireplace.

1. Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
Seaport District
United States
joanne
NT$8,465
NT$11,168 total
includes taxes & fees
Nov 11 - Nov 12
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 large hotel with a curved facade and the name "Encore" illuminated on the top.
A grand hotel with a prominent marquee, a large staircase, and well-maintained gardens.
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.

2. Encore Boston Harbor

Encore Boston Harbor
Everett
United States
Jermaine
NT$8,983
NT$10,034 total
includes taxes & fees
Nov 4 - Nov 5
Encore Boston Harbor
A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
An outdoor cafe with tables and chairs, a stone facade, and flags.
A large, classical building with multiple windows and a prominent entrance.
A modern living room with a sofa, armchair, and coffee table, a television, and a bookshelf.

3. The Langham, Boston

The Langham, Boston
Downtown Boston
United States
Mark
NT$15,727
NT$18,314 total
includes taxes & fees
Nov 13 - Nov 14
The Langham, Boston
A courtyard with brick walls, outdoor seating, and potted plants.
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.
A modern indoor pool area with large windows, comfortable seating, and a city view.

4. Four Seasons Hotel Boston

Four Seasons Hotel Boston
Bay Village
United States
Roxane
NT$26,533
NT$30,897 total
includes taxes & fees
Nov 1 - Nov 2
Four Seasons Hotel Boston
The Charles Hotel with outdoor seating and a garden area.
A hotel with a brick facade, large windows, and a prominent entrance with a glass door.
A restaurant with a wooden table centerpiece, orchid plants, and a sign for Henrietta's Table.
A spacious lobby with a central staircase, bookshelves, a red sofa, and a coffee table.

5. The Charles Hotel

The Charles Hotel
West Cambridge
Switzerland
Andre
NT$11,862
NT$13,754 total
includes taxes & fees
Nov 13 - Nov 14
The Charles Hotel
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 banquet hall with tables set for a formal event, featuring floral centerpieces and chandeliers.
A room with a large window overlooking a marina, featuring a sofa set, two side tables, and a patterned rug.

6. Boston Harbor Hotel

Boston Harbor Hotel
North End
United States
Dorothy
NT$19,542
NT$22,775 total
includes taxes & fees
Nov 1 - Nov 2
Boston Harbor Hotel
A rooftop dining area with a round table set for two, surrounded by plush seating and potted plants.
A park with a lamp post, a bridge, and buildings in the background.
A bar area with seating, a fireplace, and bookshelves.
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
Farah
NT$18,991
NT$23,800 total
includes taxes & fees
Nov 1 - Nov 2
The Newbury Boston
A modern building with a glass facade, a waterfront view, and a dock area with boats.
A spacious, well-lit event space with a reflective floor, large windows, and elegant floral centerpieces.
A table with a variety of food and drink items, including a bottle of champagne, glasses, and macarons, set against a cityscape view.
A modern lobby with a central seating area, a reception desk, and a distinctive geometric light fixture.

8. InterContinental Boston by IHG

InterContinental Boston by IHG
Downtown Boston
United States
Stepan S
NT$9,554
NT$12,587 total
includes taxes & fees
Nov 15 - Nov 16
InterContinental Boston by IHG
A modern indoor pool area with a large window, a woman in a swimsuit, and two lounge chairs.
A hotel room with a large window offering a city view, a bed, a chair, and a small table with a tray.
A modern rooftop terrace with wicker furniture, a glass balustrade, and a view of historic buildings.
A modern hotel room with a curved seating area, a coffee table, and a view of the cityscape through large windows.

9. Four Seasons Hotel One Dalton Street, Boston

Four Seasons Hotel One Dalton Street, Boston
Fenway–Kenmore
United States
Masooda
NT$21,387
NT$24,905 total
includes taxes & fees
Nov 10 - Nov 11
Four Seasons Hotel One Dalton Street, Boston
A modern bar area with multiple seating options, a well-stocked bar counter, and a distinctive ceiling design.
A modern restaurant with round tables, white cushioned seating, and circular ceiling lights.
An outdoor dining area with tables set for two, potted plants, and a sign for Ramsay's Kitchen by Gordon Ramsay.
A modern lounge with two sofas, a fireplace, and a unique ceiling chandelier.

10. Mandarin Oriental, Boston

Mandarin Oriental, Boston
Back Bay
United States
Matthew
NT$21,226
NT$24,718 total
includes taxes & fees
Nov 8 - Nov 9
Mandarin Oriental, Boston
Pool
A modern bar/lounge area with green seating, large windows, and city views.
A modern lobby with a staircase, seating area, and large windows offering city views.
A modern hotel room with a large window, a sofa, a red armchair, a round coffee table, and a bed with a view of the cityscape.

11. Raffles Boston

Raffles Boston
Back Bay
United States
Vlatko
NT$19,168
NT$22,321 total
includes taxes & fees
Nov 1 - Nov 2
Raffles Boston
A multi-level atrium with a central bar, seating areas, and a staircase.
A cobblestone street lined with brick buildings, each with a door and windows, and a street lamp on the right.
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.

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

The Liberty, a Marriott Luxury Collection Hotel, Boston
West End
United States
Gabrielle
NT$9,986
NT$12,565 total
includes taxes & fees
Nov 1 - Nov 2
The Liberty, a Marriott Luxury Collection Hotel, Boston
A hotel with a classic facade, large windows, and a prominent entrance.
A rooftop terrace with a table, chairs, and a view of the city skyline.
A hotel room with a large bed, a sofa, a desk, a television, and a fireplace.
A modern living room with a fireplace, two armchairs, a coffee table, and a zebra-patterned rug.

13. XV Beacon

XV Beacon
Beacon Hill
United States
Renee
NT$17,227
NT$20,060 total
includes taxes & fees
Nov 1 - Nov 2
XV Beacon
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.

14. The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
Downtown Boston
United States
Michael
NT$22,481
NT$27,677 total
includes taxes & fees
Nov 8 - Nov 9
The Ritz-Carlton, Boston
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 building with a sign reading "THE CELLAR" and a wooden gate.
A room with a round wooden table, two wooden chairs, a large window, and a ceiling light fixture.

15. The Bell Inn

The Bell Inn
Peabody
United States
Paul
NT$4,550
NT$5,083 total
includes taxes & fees
Nov 2 - Nov 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 large windows, a central seating area with sofas and chairs, and a modern design with a large screen on the wall.
An aerial view of a hotel courtyard with a swimming pool, outdoor seating, and greenery.
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.

16. Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett
Everett
United States
Robert
Luxury Apartments by Hyatus at Boston Everett
A modern kitchen with a large island, pendant lighting, and a view of the outdoors.
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.
A modern living room with a sectional sofa, a fireplace, and large windows offering a view of the outdoors.

17. Luxury Apartments by Hyatus Boston Somerville

Luxury Apartments by Hyatus Boston Somerville
Inner Belt
United States
Yona
Luxury Apartments by Hyatus Boston Somerville
Save an average of 15% on thousands of hotels when you're signed in

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$6,080
NT$8,177 total
Nov 1 - Nov 2
includes taxes & fees
Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

50 Park Plaza Boston MA
NT$6,260
NT$8,600 total
Nov 8 - Nov 9
includes taxes & fees
Hilton Boston Park Plaza
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10 Huntington Ave Boston MA
NT$8,724
NT$11,471 total
Oct 30 - Oct 31
includes taxes & fees
The Westin Copley Place, Boston, a Marriott Hotel
Still don't see what you're looking for?
See all properties in Winchester.
You can also use these popular filters to refine your search.
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
An aerial view of a town with a lake, church steeples, and a bridge.

Top Winchester Hotel Reviews

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

10/10 Excellent
"Great view of the city."
Jodiann 1-night trip
Posted 4 hours ago
Omni Boston Hotel at the Seaport

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$8,177
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.

Explore a world of travel with Expedia