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 4 Star Hotels

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

Our top choices for Winchester 4-star hotels

A fireplace with decorative vases, a dining table with food and drinks, and patterned ottomans.
A woman seated in a chair reading a book in a room with a fireplace, wooden floor, and decorative wall panels.
A hotel room with a large window offering a city view, a television, a patterned armchair, a sofa, and a small table with a vase of flowers.
A Seaport Hotel with a modern entrance, large windows, and a blue awning.

1. Seaport Hotel Boston

Seaport Hotel Boston
Seaport District
United States
Kathleen
4.895.072 ₫
6.583.521 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Seaport Hotel Boston
A spacious lobby with a central seating area, a bar, and a chandelier.
A spacious lobby with a modern design, featuring a sofa, armchairs, a dining area, and a large staircase.
A hotel with a classic facade, large windows, and an American flag.
A grand staircase with marble steps and ornate black railings, leading to an upper floor with a chandelier.

2. Hilton Boston Park Plaza

Hilton Boston Park Plaza
Bay Village
United States
Jane
5.040.072 ₫
6.924.304 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hilton Boston Park Plaza
A cityscape with a prominent hotel featuring a classic facade, a modern high-rise, and a historic building with arched windows.
A modern dining area with a city view, white furniture, and a blue patterned rug.
A modern hotel room with a large window offering a city view, a sofa, a coffee table, a dining area, and a flat-screen TV.
A bar area with a long counter, multiple bar stools, and a view of a building through large windows.

3. The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel
Back Bay
United States
Jean
7.022.182 ₫
9.232.730 ₫ total
includes taxes & fees
30 Oct - 31 Oct
The Westin Copley Place, Boston, a Marriott Hotel
A waterfront patio with outdoor seating, a fire pit, and a city skyline in the background.
A gym with a treadmill, dumbbells, and a small table with apples and towels.
A restaurant with tables and chairs, a view of a city skyline across a body of water, and a brick patio area.
A room with a large window overlooking a city skyline and a body of water.

4. Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor
East Boston
United States
Run
5.494.192 ₫
7.045.888 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Regency Boston Harbor
The Omni Parker House hotel facade with a classic architectural design, featuring ornate detailing and a grand entrance.
A hotel room with a large bed, a desk, a chair, a TV, and artwork on the wall.
A formal dining room with multiple tables, elegant chandeliers, and ornate wood paneling.
A covered balcony with outdoor seating, a view of a cityscape, and a building with a dome in the background.

5. Omni Parker House

Omni Parker House
Downtown Boston
United States
Racheal
7.643.614 ₫
9.956.646 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Omni Parker House
A bar area with a city view, bar stools, and a bar counter.
A modern lobby with a blue sofa, colorful ottomans, and a large window with a city view.
A modern building with a curved facade, large windows, and a glass entrance.
A modern cafe with a checkered floor, wooden tables, and a variety of food and drink options.

6. citizenM Boston Back Bay

citizenM Boston Back Bay
Fenway–Kenmore
United States
Brenda
5.333.958 ₫
6.211.395 ₫ total
includes taxes & fees
1 Nov - 2 Nov
citizenM Boston Back Bay
A multi-story hotel with a distinctive stepped design, featuring illuminated signage and a reflection in the water.
A spacious hotel lobby with a modern design, featuring a large seating area, a staircase leading to an upper floor, and a view of the city skyline through large windows.
A dining area with a long wooden table set for six, large windows with a city view, and a view of a river.
A modern hotel room with a large window offering a city view, a sofa, a teal armchair, a small table with a plant, a bed, and a TV.

7. Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge
MIT
United States
Michael
3.478.811 ₫
4.807.364 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hyatt Regency Boston/Cambridge
A restaurant with a long dining area, high ceilings, and exposed beams. Tables are set with glassware and centerpieces.
A building with a sign reading "THE DAGNY" and a brick facade. There are two bicycles parked in front.
A couple walking on a sidewalk with a restaurant named "THE DAGNY" in the background.
A grand lobby with a large arched entrance, a high ceiling with a detailed mural, and a view of the street outside.

8. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Scott
5.972.735 ₫
7.860.496 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Dagny Boston
A bar with two drinks, a candle, and a cityscape view at dusk.
A dining area with a long table set for a meal, a chandelier, and a view of the outdoors.
An indoor swimming pool with a glass ceiling, surrounded by lounge chairs and potted plants.
A river with boats docked, a bridge, and a city skyline in the background.

9. The Royal Sonesta Boston

The Royal Sonesta Boston
East Cambridge
United States
James
5.566.995 ₫
7.235.604 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Royal Sonesta Boston
A modern living room with a sofa, a coffee table, and a bookshelf filled with books and decorative items.
A modern hotel room with a large bed, a TV on the wall, and a city view.
A modern interior with large windows, a red sofa, and a city view.
A rooftop terrace with a red bench, tables, chairs, and hanging lights.

10. citizenM Boston North Station

citizenM Boston North Station
West End
United States
Anthony
5.338.696 ₫
6.216.913 ₫ total
includes taxes & fees
1 Nov - 2 Nov
citizenM Boston North Station
A spacious lobby with a central seating area, multiple levels, and a fountain.
A hotel room with a large bed, a TV, a desk, and a view of the city.
A modern hotel lobby with multiple computer stations, comfortable seating, and indoor plants.
A modern hotel room with a dining area, a sofa, and a view of the city skyline.

11. Hilton Boston Logan Airport

Hilton Boston Logan Airport
East Boston
United States
Carol
5.769.416 ₫
6.718.485 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hilton Boston Logan Airport
The exterior of the Harborside Inn Boutique Hotel with a glass entrance, numbered room 185, and two large potted plants at the entrance.
A modern lobby with leather seating, tables, and a large chandelier.
A spacious lounge area with a wooden floor, multiple seating options including sofas and ottomans, a television screen, and a ceiling with circular light fixtures.
A bar area with multiple seating options including bar stools and tables, a well-stocked liquor display, and a television screen.

12. Harborside Inn Of Boston

Harborside Inn Of Boston
Downtown Boston
United States
Sabrina
5.802.621 ₫
6.757.153 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Harborside Inn Of Boston
A restaurant with wooden flooring, multiple dining tables, and hanging chandeliers.
A building facade with multiple windows and decorative arches.
A grand arched doorway with intricate moldings and a modern light fixture above.
A grand hallway with marble walls, a staircase, and elegant seating.

13. The Godfrey Hotel Boston

The Godfrey Hotel Boston
Downtown Boston
United States
Adriana
4.870.473 ₫
6.877.762 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Godfrey Hotel Boston
A modern living room with a sectional sofa, a round coffee table, and a chandelier.
A modern living room with a gray sectional sofa, a glass coffee table, and a yellow armchair.
A hotel room with a large bed, two armchairs, a sofa, a small round table, and a mirror.
A modern hotel room with a grey sofa, a matching armchair, a small round table with a book and a plant, and a large window with a city view.

14. Hyatt Regency Boston

Hyatt Regency Boston
Downtown Boston
United Kingdom
Allison
4.641.556 ₫
6.312.153 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hyatt Regency Boston
A spacious lobby with a large mural of a city skyline and a waterfront view.
A hotel with a modern facade, multiple floors, and a prominent entrance.
A swimming pool with lounge chairs and a glass-enclosed area with a view of the city.
A modern indoor space with seating areas, a central staircase, and a wooden ceiling.

15. The Westin Boston Seaport District

The Westin Boston Seaport District
Seaport District
United States
Thomas
4.379.801 ₫
6.306.374 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Westin Boston Seaport District
A hotel room with a bed, a nightstand, a wall-mounted lamp, and a door leading to a bathroom.
The exterior of the Copley Square Hotel with its classic architecture and prominent signage.
A checkered floor, a staircase with a handrail, a round mirror, and a small table with a globe.
A reception area with a black wall, wooden desk, and pendant lighting.

16. Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
Back Bay
United States
Elena
4.895.072 ₫
5.700.311 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Copley Square Hotel, a FOUND Hotel
A rooftop lounge with outdoor seating, a fire pit, string lights, and a bar area.
A modern lounge area with seating, tables, hanging plants, and a brick wall backdrop.
A rooftop bar with a long counter, multiple chairs, and a city view at dusk.
A modern conference room with black tables, chairs, and hanging plants.

17. Revere Hotel Boston Common

Revere Hotel Boston Common
Bay Village
United States
Scott
5.705.407 ₫
7.850.992 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Revere Hotel Boston Common
A modern hotel room with large windows, a view of a cityscape, a leather armchair, a small table, and a vase with flowers.
A modern bar area with a long counter, multiple shelves of liquor bottles, and a seating area with chairs and a table.
A modern living room with a city view, a sofa, a coffee table, and a floor lamp.
A modern room with large windows, a leather sofa, a small table, and a view of a cityscape including a prominent building with a golden dome.

18. Hotel AKA Boston Common

Hotel AKA Boston Common
Downtown Boston
United Kingdom
Sarah
6.738.160 ₫
8.902.664 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Hotel AKA Boston Common
A grand entrance with an arched doorway, two large potted plants, and ornate lanterns.
A spacious lobby with a wooden herringbone floor, a central round table with a plant, and a modern chandelier.
A woman pouring champagne into a glass in a modern kitchen with dark cabinetry and a built-in oven.
A restaurant with a cozy seating area, wooden tables, and a view of the street through large windows.

19. Hotel AKA Back Bay

Hotel AKA Back Bay
Back Bay
United States
ashley
9.003.529 ₫
11.541.205 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Hotel AKA Back Bay
An outdoor seating area with tables and chairs, a bar, and a view of Fenway Park.
A view from a window with a Boston Red Sox sign in the background, a table with a bowl of cereal and a glass of beer, and a sofa with a red pillow.
A conference room with a long table set for a meeting, equipped with chairs and a chandelier.
A dining area with a long table set for multiple people, wooden chairs, and a chandelier.

20. Hotel Commonwealth

Hotel Commonwealth
Fenway–Kenmore
United States
Patricia
7.506.187 ₫
9.947.050 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hotel Commonwealth
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Winchester.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
6.821.091 ₫
8.999.496 ₫ total
11 Nov - 12 Nov
includes taxes & fees
Omni Boston Hotel at the Seaport
Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
7.231.915 ₫
8.078.049 ₫ total
4 Nov - 5 Nov
includes taxes & fees
9.6/10 Exceptional! (4,265 reviews)
Encore Boston Harbor
The Langham, Boston

The Langham, Boston

250 Franklin St Boston MA
12.661.677 ₫
14.744.522 ₫ total
15 Nov - 16 Nov
includes taxes & fees
9.8/10 Exceptional! (1,000 reviews)
The Langham, 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
An aerial view of a town with a lake, church steeples, and a bridge.

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Wonderful location, comfortable room, and helpful staff."
Karen 2-night trip
Posted 1 hour ago
Harborside Inn Of Boston
citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Good clean hotel. Location is great"
Trent 4-night trip
Posted 5 hours ago
citizenM Boston Back Bay
The Dagny Boston

The Dagny Boston

10/10 Excellent
"Breakfast at the Dagny is top notch! I had the SW burrito, and have had the Ham & Cheese sandie… both.. INCREDIBLE!"
Robert 1-night trip
Posted 5 hours ago
The Dagny Boston

Frequently asked questions

What are the best 4-star hotels in Winchester?
If you're searching for high-quality comfort and loads of amenities during your Winchester adventure, check out Boston Marriott Burlington. This sought-after 4-star hotel features premium bedding and a terrace. Freepoint Hotel Cambridge, Tapestry Collection by Hilton also gets top reviews from Expedia guests. A pillowtop mattress and concierge services are among its conveniences.
How much does it cost to stay in a 4-star hotel in Winchester?
To find a 4-star hotel in Winchester that matches your budget, make use of Expedia's search and sort filters. Take a look at what's available during your holiday dates and use our pricing filter to set your limit. You can also list your results by the most affordable option first.
  • Search for the lowest price from 8.078.049 ₫
What's the difference between 5-star and 4-star hotels in Winchester?
Treat yourself to luxury during your Winchester holiday by staying at a 4-star hotel. As well as featuring upmarket surroundings, these retreats are usually packed with amenities like complimentary bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your trip an even more indulgent and unforgettable one. 24-hour concierge assistance, elegant décor and world-class dining are only the start of the exclusive conveniences and services you'll likely get access to.

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