Title: 4 Stars Hotels in Winchester, Boston from CA $217 - Find Cheap Winchester Hotels With 4 Stars | Expedia.ca

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![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Winchester 4 Star Hotels

Tonight

[Apr 2 - Apr 3](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-02&endDate=2026-04-03&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Apr 3 - Apr 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester 4-star hotels

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/3aa5107f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6238869c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Boston Park Plaza

[](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information)

Bay Village

8.4/10

Very good

(3,122 reviews)

"Enjoyed our stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Destiny Alyssa

CA $248

CA $346 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/3a90f50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e07ab872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Harbour View | Living area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e5a155fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seaport Hotel Boston

[](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information)

Seaport District

9.6/10

Exceptional

(4,121 reviews)

"it was a great stay- would definitely come again!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Sandra

CA $176

CA $253 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/3ea105e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch and brunch served](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/a6e3ccac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Omni Parker House 

[](https://www.expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information)

Downtown Boston

9.0/10

Wonderful

(3,355 reviews)

"Great location, and beautiful hotel!!! Would definitely stay again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeremy

CA $341

CA $445 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Suite](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/b1eb6e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/f06ad8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![37-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/34618491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Boston Logan Airport

[](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information)

East Boston

9.0/10

Wonderful

(3,706 reviews)

"Great place ti stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

CA $343

CA $400 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/65e6256b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/754f64e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harborside Inn Of Boston

[](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information)

Downtown Boston

9.2/10

Wonderful

(6,410 reviews)

"It was a great location spot and affordable compared to other hotels"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kayla

CA $186

CA $217 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior detail](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/328c763f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/80b97ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bicycling](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/b4f639c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Dagny Boston

[](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information)

Downtown Boston

9.4/10

Exceptional

(7,162 reviews)

"Lovely hotel that is located on a quiet street, easily accessible to historical sites, and wonderful restaurants, All staff very nice and helpful! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenny Turpen

CA $249

CA $339 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information)

![City view](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/19346b33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/d71491e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 5:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/a909682d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/23687f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sheraton Boston, a Marriott Hotel

[](https://www.expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information)

Back Bay

8.6/10

Excellent

(1,793 reviews)

"Clean room, easy check in, great to be connected to shopping and dining"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dorthy

CA $373

CA $435 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information)

![International cuisine](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/d17a08ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/61974d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/98af3a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### citizenM Boston Back Bay

[](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information)

Fenway–Kenmore

9.4/10

Exceptional

(2,507 reviews)

"Excellent hotel "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura

CA $241

CA $281 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/7c57b7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0277dcdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 1 King Bed (View)](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/23e9f070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### citizenM Boston North Station

[](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)

West End

9.4/10

Exceptional

(4,467 reviews)

"The bar staff was quick and nice, room clean, check in was easy, breakfast delicious. We enjoyed our stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justin

CA $200

CA $233 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)

![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/eb7322a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/db3fd34b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3aefc22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Godfrey Hotel Boston

[](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information)

Downtown Boston

9.4/10

Exceptional

(4,978 reviews)

"Great staff, great location with very clean rooms. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hami

CA $145

CA $234 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/935543a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor wedding](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/72d06e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Suite](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/1ff5a711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Boston/Cambridge

[](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)

MIT

9.0/10

Wonderful

(2,283 reviews)

"great staff and clean hotel!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Natalie

CA $210

CA $275 total

includes taxes & fees

Apr 26 - Apr 27

[](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/0c21f6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/a3f6b9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Kitchenette](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/b664eae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/b6468cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Club Quarters Hotel Faneuil Hall, Boston

[](https://www.expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information)

Downtown Boston

9.0/10

Wonderful

(3,008 reviews)

"Great place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Byron

CA $304

CA $354 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information)

![Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/84f4c8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/6306f7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive Room, Terrace | Living area](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/17c5a38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Regency Boston

[](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information)

Downtown Boston

9.0/10

Wonderful

(1,947 reviews)

"We enjoyed our stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deborah

CA $200

CA $281 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information)

![Boating](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/bef3e4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Serves lunch and dinner](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/5cf99839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/d7fa2feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/w5752h3835x5y5-de17c236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Boston Back Bay

[](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information)

Fenway–Kenmore

8.4/10

Very good

(1,276 reviews)

"Great location!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Liza

CA $158

CA $233 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070718/5066927d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070718/97de3d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070718/bd847a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070718/13063cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel AKA Back Bay

[](https://www.expedia.ca/Boston-Hotels-Hotel-AKA-Back-Bay.h1070718.Hotel-Information)

Back Bay

9.4/10

Exceptional

(1,201 reviews)

"Excellent stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gabrielle

CA $301

CA $407 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Hotel-AKA-Back-Bay.h1070718.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/6a60b4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/db068914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/2d52c679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/d95fe559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lenox Hotel Boston

[](https://www.expedia.ca/Boston-Hotels-The-Lenox-Hotel-Boston.h6446.Hotel-Information)

Back Bay

9.6/10

Exceptional

(1,452 reviews)

"Great hotel and location "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer

CA $368

CA $429 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-The-Lenox-Hotel-Boston.h6446.Hotel-Information)

![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/a1ab1c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/e1a64100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/b7112317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Copley Square Hotel, a FOUND Hotel

[](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information)

Back Bay

8.6/10

Excellent

(3,988 reviews)

"Great location in Back Bay, room are on the smaller side but very clean and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carolyne

CA $193

CA $225 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/0ed5a88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/6cfad146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/aaa64f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/2b0d79ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Revere Hotel Boston Common

[](https://www.expedia.ca/Boston-Hotels-Revere-Hotel-Boston-Common.h16680.Hotel-Information)

Bay Village

9.0/10

Wonderful

(1,964 reviews)

"The hotel was great. The staff was very helpful and the rooms were clean and comfortable. I will definitely be staying there again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Irania

CA $231

CA $333 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-Revere-Hotel-Boston-Common.h16680.Hotel-Information)

![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/6c2b250e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/4d82f9e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/73d19b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/aca50fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Charles Hotel

[](https://www.expedia.ca/Boston-Hotels-The-Charles-Hotel.h15861.Hotel-Information)

West Cambridge

9.4/10

Exceptional

(1,000 reviews)

"Loved our stay."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Conrad

CA $537

CA $623 total

includes taxes & fees

May 2 - May 3

[](https://www.expedia.ca/Boston-Hotels-The-Charles-Hotel.h15861.Hotel-Information)

![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/54848539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/04a71950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/0c099f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast served](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/d6773212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Colonnade Hotel Back Bay

[](https://www.expedia.ca/Boston-Hotels-The-Colonnade-Hotel-Back-Bay.h12660.Hotel-Information)

Back Bay

9.2/10

Wonderful

(2,287 reviews)

"Great location the restaurant was excellent, staff super friendly highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeff

CA $342

CA $447 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Boston-Hotels-The-Colonnade-Hotel-Back-Bay.h12660.Hotel-Information)

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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](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

CA $214

CA $306 total

Apr 5 - Apr 6

includes taxes & fees

9.2/10 Wonderful! (4,549 reviews)

[](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information)

![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/a1d3b824_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Encore Boston Harbor

1 Broadway Everett MA

CA $338

CA $378 total

Apr 29 - Apr 30

includes taxes & fees

9.6/10 Exceptional! (3,620 reviews)

[](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information)

![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Langham, Boston

250 Franklin St Boston MA

CA $631

CA $735 total

Apr 5 - Apr 6

includes taxes & fees

9.6/10 Exceptional! (1,000 reviews)

[](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information)

Still don't see what you're looking for?

[See all properties in Winchester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=175481&star=40)

You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=175481&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=175481&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=175481&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=175481&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&regionId=175481&star=40&star=40&amenities=WATER_PARK)

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](https://www.expedia.ca/Hotel-Search?startDate=2026-04-16&endDate=2026-04-17&adults=2&regionId=175481)

![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high)

## Top Winchester Hotel Reviews

![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg)

### Harborside Inn Of Boston

10/10 Excellent

"Affordable, Very clean, excellent location. Overall great choice "

[](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information)

![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg)

### The Dagny Boston

10/10 Excellent

"Everything was great, staff is very welcoming "

[](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information)

![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg)

### Seaport Hotel Boston

10/10 Excellent

"we love staying at the Seaport hotel! they decorate it so beautifully at Christmastime. the staff is always so helpful and attentive and will go above & beyond for you and your circumstances if they can! we stay here once a year & will continue to do so!"

[](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information)

![Club Quarters Hotel Faneuil Hall, Boston](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/0c21f6a5_y.jpg)

### Club Quarters Hotel Faneuil Hall, Boston

10/10 Excellent

"stayed 3 nights for business. perfect location."

[](https://expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information)

![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/c254df3c_y.jpg)

### The Godfrey Hotel Boston

10/10 Excellent

"Spent a wonderful night with my sister for her birthday. The staff was amazing and even sent champagne and chocolate to our room for her big day!! We loved how centrally located the hotel is to downtown. We could walk to everything!! I will definitely be back!!"

[](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information)

![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5_y.jpg)

### citizenM Boston Back Bay

8/10 Good

"Room was great, ipad plug in didnt work so ipad always dying, 4th floor hall carpets were dirty, gym was closed due to construction. Ironing station was down the hall, little water in it, a learning curve to use. Not one glass in the roon.Reilly was very nice at front desk. The rest of staff aloof. Did not eat "

[](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information)

![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9_y.jpg)

### Hilton Boston Logan Airport

10/10 Excellent

"Clean rooms. Wonderful staff. Easy to get to airport "

[](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information)

![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg)

### Hyatt Regency Boston/Cambridge

10/10 Excellent

"Staffs were kind and shuttle service was excellent. We will stay again when we will visit next time."

[](https://expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)

![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg)

### Hilton Boston Park Plaza

6/10 Okay

"The heater was so loud, I couldn’t sleep well."

[](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information)

## Find out more about Winchester

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Winchester are calling your name. Known for providing first-rate service in amazing locations, each of the Winchester 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Winchester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Winchester, Boston, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Winchester hotels with 4 Stars provide everything you need to unwind in style.

## Frequently asked questions

### What are the best 4-star hotels in Winchester?

### How much does it cost to stay in a 4-star hotel in Winchester?

> - Search for the lowest price from CA $306

### What's the difference between 5-star and 4-star hotels in Winchester?

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