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
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 4-star hotels

A high-rise hotel with multiple floors, large windows, and a waterfront view.
An indoor swimming pool with a skylight ceiling, seating area with cushions, and a 'No Diving' sign.
A fireplace with decorative vases, a dining table with food and drinks, and patterned ottomans.
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.

1. Seaport Hotel Boston

Seaport Hotel Boston
Seaport District
United States
Cordell
5.128.239 ₫
6.861.355 ₫ total
includes taxes & fees
20 Sept - 21 Sept
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 grand staircase with marble steps and ornate black railings, leading to an upper floor with a chandelier.
A spacious lobby with a grand chandelier, a reception desk, and a seating area with a table and chairs.

2. Hilton Boston Park Plaza

Hilton Boston Park Plaza
Bay Village
United States
Aimee
4.683.087 ₫
6.516.135 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Hilton Boston Park Plaza
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 library with leather sofas, bookshelves, and a large chandelier.
A couple walking on a sidewalk with a restaurant named "THE DAGNY" in the background.

3. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Isabella
6.548.186 ₫
8.536.268 ₫ total
includes taxes & fees
13 Sept - 14 Sept
The Dagny Boston
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 luxurious lobby with ornate wood paneling, a grand chandelier, and elegant seating arrangements.
A covered balcony with outdoor seating, a view of a cityscape, and a building with a dome in the background.

4. Omni Parker House

Omni Parker House
Downtown Boston
United States
Liv
6.232.903 ₫
8.321.416 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Omni Parker House
A spacious lobby with a large mural of a city skyline and a waterfront view.
A modern building with a restaurant named "O'Connors" on the ground floor.
A hotel with a modern facade, multiple floors, and a prominent entrance.
A modern indoor space with seating areas, a central staircase, and a wooden ceiling.

5. The Westin Boston Seaport District

The Westin Boston Seaport District
Seaport District
United States
Colby
4.201.166 ₫
6.106.972 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Westin Boston Seaport District
A multi-story hotel with a distinctive stepped design, featuring illuminated signage and a reflection in the water.
An outdoor seating area with wooden tables and chairs, surrounded by greenery and illuminated by lanterns.
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.
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.

6. Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge
MIT
United States
charlene
4.186.226 ₫
5.633.140 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Hyatt Regency Boston/Cambridge
The exterior of the Harborside Inn Boutique Hotel with a glass entrance, numbered room 185, and two large potted plants at the entrance.
A bar area with multiple seating options including bar stools and tables, a well-stocked liquor display, and a television screen.
An outdoor cafe with tables and chairs, a building entrance, and a street sign.
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.

7. Harborside Inn Of Boston

Harborside Inn Of Boston
Downtown Boston
United States
Laura
4.905.272 ₫
5.712.189 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Harborside Inn Of Boston
A bar area with a city view, bar stools, and a bar counter.
A modern cafe with a checkered floor, wooden tables, and a variety of food and drink options.
A modern building with a curved facade, large windows, and a glass entrance.
A modern lobby with a blue sofa, colorful ottomans, and a large window with a city view.

8. citizenM Boston Back Bay

citizenM Boston Back Bay
Fenway–Kenmore
United States
Adrian
4.198.558 ₫
4.889.220 ₫ total
includes taxes & fees
7 Sept - 8 Sept
citizenM Boston Back Bay
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 bar area with a long counter, multiple bar stools, and a view of a building through large windows.
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.

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

The Westin Copley Place, Boston, a Marriott Hotel
Back Bay
United States
Tara
7.072.354 ₫
9.298.696 ₫ total
includes taxes & fees
6 Sept - 7 Sept
The Westin Copley Place, Boston, a Marriott Hotel
A bar with two drinks, a candle, and a cityscape view at dusk.
A river with boats docked, a bridge, and a city skyline in the background.
An indoor swimming pool with a glass ceiling, surrounded by lounge chairs and potted plants.
A modern room with large windows, a round table, two chairs, and a decorative vase.

10. The Royal Sonesta Boston

The Royal Sonesta Boston
East Cambridge
Canada
Chrissy
4.146.402 ₫
5.594.005 ₫ total
includes taxes & fees
6 Sept - 7 Sept
The Royal Sonesta Boston
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 modern interior with seating, a table with wine glasses, and a display of books and decorative items.
A modern conference room with black tables, chairs, and hanging plants.

11. Revere Hotel Boston Common

Revere Hotel Boston Common
Bay Village
United States
Elena
5.962.735 ₫
8.158.242 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Revere Hotel Boston Common
A spacious lobby with a central seating area, multiple levels, and a fountain.
A hotel room with a large window offering a view of an airport, including parked airplanes and airport buildings.
A modern hotel room with a dining area, a sofa, and a view of the city skyline.
A hotel room with a large bed, a TV, a desk, and a view of the city.

12. Hilton Boston Logan Airport

Hilton Boston Logan Airport
East Boston
United States
Karen
6.493.422 ₫
7.561.589 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Hilton Boston Logan Airport
A modern living room with a sectional sofa, a round coffee table, and a chandelier.
A modern lobby with large windows, a bench, and a unique ceiling light fixture.
A hotel room with two beds, a flat-screen TV, a desk, a chair, and a view of the city.
A modern bar area with a long counter, multiple seating options, and a view of the cityscape through large windows.

13. Hyatt Regency Boston

Hyatt Regency Boston
Downtown Boston
United Kingdom
Valerie
5.374.676 ₫
7.171.540 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Hyatt Regency Boston
An indoor swimming pool with clear views of the outdoors, sunlit ceiling, and lounge chairs.
A DoubleTree hotel with a modern facade, multiple entry points, and well-maintained landscaping.
A lobby with a sofa, armchairs, a coffee table, and a potted plant.
A vibrant restaurant with colorful architecture, including a distinctive roof and wavy railings.

14. DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore
Danvers
United States
Gavindra
3.103.282 ₫
3.466.288 ₫ total
includes taxes & fees
31 Aug - 1 Sept
DoubleTree by Hilton Boston North Shore
A hotel room with a bed, a nightstand, a wall-mounted lamp, and a door leading to a bathroom.
A restaurant interior with booths, tables, and a textured wall.
A reception area with a black wall, wooden desk, and pendant lighting.
A checkered floor, a staircase with a handrail, a round mirror, and a small table with a globe.

15. Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
Back Bay
Canada
Courtney
4.434.564 ₫
5.164.051 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Copley Square Hotel, a FOUND Hotel
A modern living room with a sofa, a coffee table, and a bookshelf filled with books and decorative items.
A modern building with a glass facade, a sign for TD Garden, and a North Station sign.
A rooftop terrace with a red bench, tables, chairs, and hanging lights.
A modern interior with large windows, a red sofa, and a city view.

16. citizenM Boston North Station

citizenM Boston North Station
West End
United States
Nicole
4.433.260 ₫
5.162.531 ₫ total
includes taxes & fees
7 Sept - 8 Sept
citizenM Boston North Station
A restaurant with wooden flooring, multiple dining tables, and hanging chandeliers.
A grand hallway with marble walls, a staircase, and elegant seating.
A bar area with a long counter, multiple bar stools, and a decorative mural on the wall.
A building facade with multiple windows and decorative arches.

17. The Godfrey Hotel Boston

The Godfrey Hotel Boston
Downtown Boston
United States
Joseph Brett
4.975.682 ₫
6.857.382 ₫ total
includes taxes & fees
6 Sept - 7 Sept
The Godfrey Hotel Boston
A modern lounge area with sofas, round tables, and a bar with multiple seating options.
A modern living room with a sectional sofa, a round coffee table, and a floor lamp with lights.
A modern interior with a bar area, seating, and a unique black coffee table.
A modern kitchen with a marble countertop, bar stools, and a flat-screen TV mounted on the wall.

18. Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea
Chelsea
United States
Gemina
4.469.248 ₫
4.992.150 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Doubletree By Hilton Boston Logan Airport Chelsea
A rooftop pool area with lounge chairs and umbrellas, overlooking a cityscape.
A modern lounge area with a grey sofa, yellow chairs, and a chandelier.
A modern restaurant with high ceilings, pendant lighting, and a mix of dining tables and seating areas.
A modern living room with a fireplace, comfortable seating, and built-in bookshelves.

19. The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay
Back Bay
United States
Amber
6.372.643 ₫
8.332.108 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Colonnade Hotel Back Bay
A bar area with wooden stools, a bar counter, and a decorative ceiling.
A hotel room with a bed, a desk with a laptop and headphones, a chair, a bedside table with a lamp, and a large window with curtains.
A building with a large number '161' sign, Club Quarters flags, and a storefront with 'STLE PUB' signage.
A spacious lobby with a central seating area, a fireplace, and a variety of decorative items on shelves.

20. Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
United States
Valentina
6.024.018 ₫
7.014.970 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Club Quarters Hotel Faneuil Hall, Boston
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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
7.072.354 ₫
9.298.694 ₫ total
6 Sept - 7 Sept
includes taxes & fees
9.2/10 Wonderful! (4,829 reviews)
Omni Boston Hotel at the Seaport
Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
7.466.131 ₫
8.339.669 ₫ total
21 Sept - 22 Sept
includes taxes & fees
Encore Boston Harbor
The Langham, Boston

The Langham, Boston

250 Franklin St Boston MA
13.690.950 ₫
15.943.112 ₫ total
3 Sept - 4 Sept
includes taxes & fees
The Langham, Boston
Still don't see what you're looking for?
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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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Lovely hotel with character. Well situated for all the tourist attractions."
Paula 2-night trip
Posted less than an hour ago
The Godfrey Hotel Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"No microwave in room"
Craig 4-night trip
Posted 1 hour ago
Harborside Inn Of Boston
Seaport Hotel Boston

Seaport Hotel Boston

8/10 Good
"Great location and wonderful hotel. Computers were down when we arrived so checked our bags and returned later to check-in. Room was great. Unfortunately, the alarm was sounded at 3:15am and we had to evacuate the hotel. The next morning when checking out there was no apology about the alarm and it was during checkout that we were informed of a $35 credit we had for our room. This could have been conveyed to us when we checked-in."
Chris 1-night trip
Posted 1 hour ago
Seaport Hotel Boston
The Dagny Boston

The Dagny Boston

10/10 Excellent
"We loved this hotel, it has a really warm feel to it and the rooms are decorated really nicely. The cafe attached to it is great for breakfast and again it has a really nice atmosphere and the food prices are reasonable . We would definitely stay here again"
Kelly 2-night trip
Posted 1 hour ago
The Dagny Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Very friendly and helpful staff"
Sanita 2-night trip
Posted 1 hour ago
Hyatt Regency Boston/Cambridge
citizenM Boston North Station

citizenM Boston North Station

10/10 Excellent
"The property was in the right spot where everything we needed to do"
Anthony 2-night trip
Posted 2 hours ago
citizenM Boston North Station
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

8/10 Good
"Great location!"
Isabella 1-night trip
Posted 14 hours ago
Club Quarters Hotel Faneuil Hall, Boston
citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"This is the first time staying at one of these properties, but I would do it again in a heartbeat. The room was small, but modern and comfortable. I loved having the bed up against a huge window looking out over the city - a nice touch. The self-check in was new to me, but it was fast and easy. The food at the the rooftop bar was incredible. All and all, I'll definitely be staying here again, and I will look for the same property in other cities going forward if traveling solo."
Jill 2-night trip
Posted 1 day ago
citizenM Boston Back Bay

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 8.339.669 ₫
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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