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
Oct 24 - Oct 25
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Oct 25 - Oct 26
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Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Winchester 4-star hotels

A fireplace with decorative vases, a dining table with food and drinks, and patterned ottomans.
A multi-story hotel with a corner entrance, large windows, and a visible restaurant sign.
An indoor swimming pool with a skylight ceiling, seating area with cushions, and a 'No Diving' sign.
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
Ebony
$176 nightly
$204 total
Nov 24 - Nov 25
Total with taxes and fees
Seaport Hotel Boston
A cityscape with a prominent hotel featuring a classic facade, a modern high-rise, and a historic building with arched windows.
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.
A modern dining area with a city view, white furniture, and a blue patterned rug.

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

The Westin Copley Place, Boston, a Marriott Hotel
Back Bay
United States
Jean
$207 nightly
$241 total
Nov 22 - Nov 23
Total with taxes and fees
The Westin Copley Place, Boston, a Marriott Hotel
A brick building with a large arched entrance, two flags, and a sign reading "THE DAGNY".
A couple walking on a sidewalk with a restaurant named "THE DAGNY" in the background.
A restaurant with a long dining area, high ceilings, and exposed beams. Tables are set with glassware and centerpieces.
A grand lobby with a large arched entrance, a high ceiling with a detailed mural, and a view of the street outside.

3. The Dagny Boston

The Dagny Boston
Downtown Boston
United States
Jonathan
$188 nightly
$219 total
Nov 22 - Nov 23
Total with taxes and fees
The Dagny Boston
A modern lobby with a blue sofa, colorful ottomans, and a large window with a city view.
An outdoor seating area with a green sofa, a blue chair, and red chairs.
A modern cafe with a checkered floor, wooden tables, and a variety of food and drink options.
A bar area with a city view, bar stools, and a bar counter.

4. citizenM Boston Back Bay

citizenM Boston Back Bay
Fenway–Kenmore
United States
Heather
$134 nightly
$156 total
Nov 23 - Nov 24
Total with taxes and fees
citizenM Boston Back Bay
The Omni Parker House hotel facade with a classic architectural design, featuring ornate detailing and a grand entrance.
A covered balcony with outdoor seating, a view of a cityscape, and a building with a dome in the background.
A luxurious lobby with ornate wood paneling, a grand chandelier, and elegant seating arrangements.
A formal dining room with multiple tables, elegant chandeliers, and ornate wood paneling.

5. Omni Parker House

Omni Parker House
Downtown Boston
United States
Racheal
$204 nightly
$238 total
Nov 23 - Nov 24
Total with taxes and fees
Omni Parker House
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.
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.

6. The Royal Sonesta Boston

The Royal Sonesta Boston
East Cambridge
United States
James
$145 nightly
$168 total
Nov 22 - Nov 23
Total with taxes and fees
The Royal Sonesta Boston
A rooftop lounge with outdoor seating, a fire pit, string lights, and a bar area.
A modern conference room with black tables, chairs, and hanging plants.
A rooftop bar with a long counter, multiple chairs, and a city view at dusk.
A modern lounge area with seating, tables, hanging plants, and a brick wall backdrop.

7. Revere Hotel Boston Common

Revere Hotel Boston Common
Bay Village
United States
Joe
$195 nightly
$227 total
Nov 23 - Nov 24
Total with taxes and fees
Revere Hotel Boston Common
A modern living room with a sofa, a coffee table, and a bookshelf filled with books and decorative items.
A modern interior with large windows, a red sofa, and a city view.
A modern hotel room with a large bed, a TV on the wall, and a city view.
A rooftop terrace with a red bench, tables, chairs, and hanging lights.

8. citizenM Boston North Station

citizenM Boston North Station
West End
United States
Anthony
$125 nightly
$146 total
Nov 24 - Nov 25
Total with taxes and fees
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.

9. Hilton Boston Logan Airport

Hilton Boston Logan Airport
East Boston
United States
Jay
$127 nightly
$147 total
Nov 24 - Nov 25
Total with taxes and fees
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.
An outdoor cafe with tables and chairs, a building entrance, and a street sign.
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.

10. Harborside Inn Of Boston

Harborside Inn Of Boston
Downtown Boston
United States
Donna
$129 nightly
$150 total
Nov 22 - Nov 23
Total with taxes and fees
Harborside Inn Of Boston
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 modern bar area with a long counter, blue chairs, and a variety of bottles and glasses.
A restaurant with tables and chairs, a view of a city skyline across a body of water, and a brick patio area.

11. Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor
East Boston
United States
Run
$154 nightly
$179 total
Nov 22 - Nov 23
Total with taxes and fees
Hyatt Regency Boston Harbor
A multi-story hotel with a distinctive stepped design, featuring illuminated signage and a reflection in the water.
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 dining area with a long wooden table set for six, large windows with a city view, and a view of a river.
An outdoor seating area with wooden tables and chairs, surrounded by greenery and illuminated by lanterns.

12. Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge
MIT
United States
Dawn
$152 nightly
$176 total
Nov 24 - Nov 25
Total with taxes and fees
Hyatt Regency Boston/Cambridge
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.
A modern living room with a gray sectional sofa, a glass coffee table, and a yellow armchair.
Two people dining at a restaurant with various dishes and drinks on the table.
A hotel room with a large bed, two armchairs, a sofa, a small round table, and a mirror.

13. Hyatt Regency Boston

Hyatt Regency Boston
Downtown Boston
United States
Steffanie
$164 nightly
$191 total
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Boston
A hotel room with a bed, a desk, a chair, a TV, and a shower area.
A rooftop bar with a city skyline view, outdoor seating, and string lights.
Restaurant
A person using a Peloton stationary bike in a gym with exercise equipment in the background.

14. YOTEL Boston

YOTEL Boston
Seaport District
United States
Stacy Lee
$162 nightly
$189 total
Nov 22 - Nov 23
Total with taxes and fees
YOTEL Boston
A hotel room with a bed, a nightstand, a wall-mounted lamp, and a door leading to a bathroom.
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.
A restaurant interior with booths, tables, and a textured wall.

15. Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
Back Bay
United States
Elena
$119 nightly
$139 total
Nov 24 - Nov 25
Total with taxes and fees
Copley Square Hotel, a FOUND Hotel
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 room with large windows, a leather sofa, a small table, and a view of a cityscape including a prominent building with a golden dome.
A hotel room with a large bed, a leather armchair, a small round table with a clock, and a view of the city through large windows.

16. Hotel AKA Boston Common

Hotel AKA Boston Common
Downtown Boston
United States
Ginger
$215 nightly
$250 total
Nov 22 - Nov 23
Total with taxes and fees
Hotel AKA Boston Common
A spacious lobby with a central seating area, a bar with a wine display, and a chandelier.
A grand staircase with ornate metal railings and marble steps.
A library with bookshelves, two leather chairs, a patterned wall, and a ceiling light fixture.
A hotel room with a large bed, a desk, a chair, a sofa, and a TV.

17. Hilton Boston Park Plaza

Hilton Boston Park Plaza
Bay Village
United States
Lena M
$162 nightly
$188 total
Nov 24 - Nov 25
Total with taxes and fees
Hilton Boston Park Plaza
A high-rise hotel with multiple floors, a central courtyard, and a parking area.
A modern dining area with a large table, six chairs, and a city view through large windows.
A modern indoor pool with clear blue water, surrounded by lounge chairs and a city view through large windows.
A spacious lobby with seating areas, a reception desk, and a high ceiling with recessed lighting.

18. Boston Marriott Copley Place

Boston Marriott Copley Place
Back Bay
United States
Rodrigo
$196 nightly
$228 total
Nov 22 - Nov 23
Total with taxes and fees
Boston Marriott Copley Place
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 restaurant with a cozy seating area, wooden tables, and a view of the street through large windows.
A woman pouring champagne into a glass in a modern kitchen with dark cabinetry and a built-in oven.

19. Hotel AKA Back Bay

Hotel AKA Back Bay
Back Bay
United States
Amit
$240 nightly
$280 total
Nov 22 - Nov 23
Total with taxes and fees
Hotel AKA Back Bay
A grand lobby with a high ceiling, ornate columns, and a large chandelier.
A historic building with a classic architectural style, featuring a symmetrical facade, multiple windows, and a prominent entrance with a covered walkway.
A grand lobby with a marble floor, ornate ceiling, and a large chandelier.
A grand ballroom with ornate architecture, chandeliers, and a grand piano. Tables are set with fine dining ware and flowers.

20. Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston
Back Bay
United States
Elizabeth
$289 nightly
$331 total
Nov 22 - Nov 23
Total with taxes and fees
Fairmont Copley Plaza, 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
$219 nightly
$255 total
Nov 22 - Nov 23
Total with taxes and fees
9.2/10 Wonderful! (4,933 reviews)
Omni Boston Hotel at the Seaport
Encore Boston Harbor

Encore Boston Harbor

1 Broadway Everett MA
$244 nightly
$273 total
Nov 23 - Nov 24
Total with taxes and fees
Encore Boston Harbor
The Charles Hotel

The Charles Hotel

One Bennett Street Cambridge MA
$307 nightly
$356 total
Nov 24 - Nov 25
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
The Charles Hotel
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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
"This hotel is in a prime location close to the freedom trail, great food, the trolley tour route, aquarium, ferry, and Quincy market. Bed was comfortable, it is an historic building so the hallways are narrow there were steps and thick carpet. It made rolling suitcases to the room very difficult. However, it did not dampen our stay. The hotel was quiet and staff were quick and helpful when our hairdryer was broken. I will stay here again."
Cayse 2-night trip
Posted 2 hours ago
Harborside Inn Of Boston
citizenM Boston Back Bay

citizenM Boston Back Bay

10/10 Excellent
"Great location and great service! I can’t wait to stay again when I come back!"
Timothy 2-night trip
Posted 3 hours ago
citizenM Boston Back Bay
Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"Very clean, great atmosphere and everyone was friendly and helpful."
Debra 1-night trip
Posted 3 hours ago
Hyatt Regency Boston
Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Front desk, staff and bellmen were very efficient and courteous. Breakfast downstairs was very good ( off the menu and buffet). I especially was impressed with the fitness center. Hotel was close to a lot different restaurants. Across the street there is the harbor walk which goes along the water and I used this every morning to run."
Edmund 3-night trip
Posted 4 hours ago
Seaport Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Great location. Nice rooms."
CHristopher 2-night trip
Posted 6 hours ago
Hilton Boston Park Plaza
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"Beautiful view, clean facilities and the complimentary clam chowder and waters were a nice touch."
Michael 1-night trip
Posted 2 days ago
Hyatt Regency Boston Harbor

Find out more about Winchester

Winchester Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Winchester, Boston are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Winchester 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Winchester. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Winchester, Boston, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Winchester hotels offer everything your heart desires.

Frequently asked questions

What are the best 4-star hotels in Winchester?
Boston Marriott Burlington is a 4-star hotel in Winchester that ranks highly among Expedia guests. Proposal/romance packages and premium bedding are a couple of its amenities. Travelers also love staying at Freepoint Hotel Cambridge, Tapestry Collection by Hilton. From a deep soaking bathtub to designer toiletries, it offers conveniences that cater to every aspect of your relaxation and entertainment.
How much does it cost to stay in a 4-star hotel in Winchester?
Expedia can help you quickly track down the perfect 4-star hotel for your stay in Winchester. Use our handy filter tool to fine-tune your search by things like price, conveniences and property star rating and get access to terrific deals in a few clicks.
  • Search for the lowest price from $255
What's the difference between 5-star and 4-star hotels in Winchester?
Treat yourself to luxury living during your Winchester escape by staying at a 4-star hotel. As well as featuring upmarket surroundings, these properties are usually packed with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go above and beyond to make your trip an even more indulgent and special one. Concierge assistance, elegant furnishings and world-class dining are a few of the superior conveniences and services you'll likely get access to.

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