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

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Check availability on Winchester 5 Star Hotels

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sep
Next weekend
4 Sep - 6 Sep
In two weeks
11 Sep - 13 Sep

Our top choices for Winchester 5-star hotels

A hotel room with a large bed, a desk, a chair, and a view of a cityscape through a large window.
A modern rooftop lounge with seating and tables, a cityscape view, and a decorative wall mural.
A modern restaurant with round tables and chairs, large windows with a city view, and a geometric patterned floor.
A modern Omni Hotel building with a glass facade, located in an urban setting with other contemporary buildings around.

1. Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
Seaport District
United States
ruby
7.072.354 ₫
9.298.694 ₫ total
includes taxes & fees
6 Sept - 7 Sept
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 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.

2. Encore Boston Harbor

Encore Boston Harbor
Everett
United States
Melissa
7.466.131 ₫
8.339.669 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Encore Boston Harbor
A spacious, elegantly designed dining area with high ceilings, chandeliers, and classic decor.
A grand hall with ornate ceiling and large windows.
A modern living room with a sofa, armchair, and coffee table, a television, and a bookshelf.
An outdoor cafe with tables and chairs, a stone facade, and flags.

3. The Langham, Boston

The Langham, Boston
Downtown Boston
United States
Cemil
13.690.950 ₫
15.943.112 ₫ total
includes taxes & fees
3 Sept - 4 Sept
The Langham, Boston
A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
A hotel room with a large bed, a TV, a desk, and a view of the sea.
A room with a large window overlooking a marina, featuring a sofa set, two side tables, and a patterned rug.
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
Dorothy
18.115.104 ₫
21.109.383 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Boston Harbor Hotel
The Charles Hotel with outdoor seating and a garden area.
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.
A staircase with a modern design, featuring a combination of brick and wood elements, and a metal railing.

5. The Charles Hotel

The Charles Hotel
West Cambridge
United States
Daniel
9.305.934 ₫
10.790.033 ₫ total
includes taxes & fees
31 Aug - 1 Sept
The Charles Hotel
A modern building with a glass facade, a waterfront view, and a dock area with boats.
A modern indoor swimming pool with clear blue water, sunlit windows, and lounge chairs along the poolside.
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.

6. InterContinental Boston by IHG

InterContinental Boston by IHG
Downtown Boston
United States
Donna
7.536.542 ₫
9.960.765 ₫ total
includes taxes & fees
7 Sept - 8 Sept
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 spacious living room with a large sofa, two armchairs, a coffee table, and a dining area with a table and chairs.
A bar area with marble countertops, blue bar stools, and a variety of bottles.

7. The Newbury Boston

The Newbury Boston
Back Bay
United States
Sandra
16.454.957 ₫
20.528.284 ₫ total
includes taxes & fees
3 Sept - 4 Sept
The Newbury 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 brick building with arched windows and a black door, surrounded by greenery and a metal fence.
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
21.514.350 ₫
25.053.461 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Four Seasons Hotel Boston
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 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 Kingdom
Liam James
17.993.820 ₫
20.953.804 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Four Seasons Hotel One Dalton Street, Boston
A multi-level atrium with a central bar, seating areas, and a staircase.
A spacious lobby with a high ceiling, a large chandelier, and a seating area with leather chairs.
A multi-level interior with hanging greenery and a bar area.
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
Lori
7.736.039 ₫
9.767.749 ₫ total
includes taxes & fees
13 Sept - 14 Sept
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 lobby with a central round table, potted plants, and artwork on the walls.
A modern lounge with two sofas, a fireplace, and a unique ceiling chandelier.
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
17.954.703 ₫
20.908.250 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Mandarin Oriental, Boston
A bar area with a city view, seating with red accents, and a plant.
A high-rise hotel lobby with large windows, a chandelier, and seating areas.
A modern lobby with a staircase, seating area, and large windows offering city views.

12. Raffles Boston

Raffles Boston
Back Bay
United States
Robinette
19.714.968 ₫
22.958.080 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Raffles Boston
A spacious lobby with a central seating area, a large chandelier, and a fireplace.
A modern hotel bathroom with a marble vanity, a large bathtub, and a city view through an open door.
A person sitting by a window with a cityscape view, a breakfast tray, and a cup.
A bar area with multiple shelves of bottles and glasses, bar stools, and a warm, well-lit ambiance.

13. The Ritz-Carlton, Boston

The Ritz-Carlton, Boston
Downtown Boston
United States
Maxim
16.403.062 ₫
19.101.613 ₫ total
includes taxes & fees
3 Sept - 4 Sept
The Ritz-Carlton, 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 sofa, a zebra-patterned rug, and a staircase leading to an upper floor.

14. XV Beacon

XV Beacon
Beacon Hill
United States
Robin
13.964.769 ₫
16.261.972 ₫ total
includes taxes & fees
31 Aug - 1 Sept
XV Beacon
A spacious room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.
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.
A room with a white wall-mounted lamp, a window with curtains, a sofa, and a patterned chair.

15. The Bell Inn

The Bell Inn
Peabody
United States
Joseph A
3.688.835 ₫
4.120.429 ₫ total
includes taxes & fees
2 Sept - 3 Sept
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
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 living room with a green sofa, a round coffee table, and a bookshelf.
A modern living room with a sectional sofa, a fireplace, and large windows offering a view of the outdoors.
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
5.128.239 ₫
6.861.355 ₫ total
20 Sept - 21 Sept
includes taxes & fees
9.6/10 Exceptional! (4,898 reviews)
Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

50 Park Plaza Boston MA
4.683.087 ₫
6.516.135 ₫ total
6 Sept - 7 Sept
includes taxes & fees
Hilton Boston Park Plaza
The Dagny Boston

The Dagny Boston

89 Broad Street Boston MA
6.548.186 ₫
8.536.268 ₫ total
13 Sept - 14 Sept
includes taxes & fees
9.6/10 Exceptional! (7,461 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?
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 6.516.135 ₫
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.

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