Title: 5 Stars Hotels in Winchester, Boston from CA $226 - Find Cheap Winchester Hotels With 5 Stars | Expedia.ca

  

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# 5 Stars Hotels in Winchester, Boston from CA $226

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## Check availability on Winchester 5 Star Hotels

Tonight

[Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-02&endDate=2025-11-03&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-03&endDate=2025-11-04&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-14&endDate=2025-11-16&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Winchester 5 Star Hotels

![View from property](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 restaurants, breakfast served](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/1ac58b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/af87cf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Omni Boston Hotel at the Seaport

Seaport District

9.2/10

Wonderful

(4214)

"Great hotel! "

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

Mark

CA $184

CA $271 total

includes taxes & fees

Nov 25 - Nov 26

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

![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/04e6a462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Nightclub](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/a6b605cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/0f4a30a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Encore Boston Harbor

Everett

9.6/10

Exceptional

(3353)

"Wonderful hotel"

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

Lian

CA $368

CA $412 total

includes taxes & fees

Dec 3 - Dec 4

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

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/400/395/357d5388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/400/395/d23d79f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Corner (House)](https://images.trvl-media.com/lodging/1000000/10000/400/395/df53de2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Newbury Boston

Back Bay

9.4/10

Exceptional

(529)

"This hotel has it all, best in class care and service."

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

Mary

CA $555

CA $720 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/e22c0556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Club Room, 1 King Bed, Park View | Park view](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9dd85bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, brunch served; Italian cuisine ](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/b09a9741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Langham, Boston

Downtown Boston

9.6/10

Exceptional

(1002)

"Excellent lodging."

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

robert

CA $497

CA $579 total

includes taxes & fees

Nov 23 - Nov 24

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

![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/6ea00b32.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/1000000/30000/22000/21962/1bab5b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/8397fde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/b4c3e1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Four Seasons Hotel Boston

Bay Village

9.4/10

Exceptional

(446)

"The Vault is so genius. The staff is beyond compare, intelligent, professional to the highest standard and very thoughtful. "

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

Alexandra

CA $1,051

CA $1,224 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Boston-Hotels-Four-Seasons-Hotel-Boston.h21962.Hotel-Information)

![Suite, Multiple Beds (John Adams Presidential Suite)](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/61473433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (Admirals Suite)](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/77e4a184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/ec21d2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boston Harbor Hotel

North End

9.8/10

Exceptional

(1006)

"One of the best I’ve stayed at in a while"

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

Bryan

CA $626

CA $730 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/45321953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4157cb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/w3891h2578x6y3-d68e82bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Corner (View) | Water view](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4175b463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### InterContinental Boston by IHG

Downtown Boston

9.4/10

Exceptional

(1009)

"Enjoyed my stay - everything is perfect. "

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

Jingying

CA $251

CA $356 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/6f89371e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite, 1 Bedroom, City View (Ebersol)](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/61c88098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bars/lounges](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/184096ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/b81f4996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Liberty, a Marriott Luxury Collection Hotel, Boston

West End

8.8/10

Excellent

(1005)

"Great Location! "

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

Diana M

CA $301

CA $386 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/7e37dec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/54668a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite, 1 Bedroom (Scenic Park & Boston Common View) | Living room](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/713a53fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Banquet hall](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/68b481c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ritz-Carlton, Boston

Downtown Boston

9.0/10

Wonderful

(406)

"Perfection. Loved the Avery bar for a cocktail at night too. Terrific staff all around and a comfortable stay."

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

Allison

CA $834

CA $971 total

includes taxes & fees

Nov 28 - Nov 29

[](https://www.expedia.ca/Boston-Hotels-The-Ritz-Carlton.h695991.Hotel-Information)

![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/a484cf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Charles) | Terrace/patio](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/cfe3865c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/0fadfa3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 restaurants, breakfast, dinner served; Japanese cuisine](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/0d9ee24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Four Seasons Hotel One Dalton Street, Boston

Back Bay

9.6/10

Exceptional

(358)

"Very nice property with great staff."

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

Eric

CA $876

CA $1,020 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Boston-Hotels-Four-Seasons-Hotel-One-Dalton-Street.h33464201.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/dcac42e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Suite, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/50462d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/w1667h2500x0y0-6219c43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Suite, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/fb990cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mandarin Oriental, Boston

Back Bay

9.4/10

Exceptional

(374)

"Staff was incredible. Spa was one of the best!"

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

angel

CA $712

CA $829 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Boston-Hotels-Mandarin-Oriental-Boston.h2175117.Hotel-Information)

![3 restaurants, breakfast, lunch, dinner served; Portuguese cuisine](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/0f66f064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/046798a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/8bef1b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Raffles Boston

Back Bay

9.6/10

Exceptional

(173)

"Amazing staff and great food"

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

Ashleigh

CA $757

CA $881 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Boston-Hotels-Boston-Common-Hotel.h911477.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/0637e89e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 King Bed (Boston Common)](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/e89c66dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/86944140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/9516aa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### XV Beacon

Beacon Hill

9.4/10

Exceptional

(381)

"Spacious and beautiful room. Love this hotel. "

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

Demery

CA $750

CA $874 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Boston-Hotels-Fifteen-Beacon.h201184.Hotel-Information)

![Honeymoon Room | In-room dining](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/39751e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/03f0119d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/1b86689c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Room | Living area](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/9e88c4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bell Inn

Peabody

9.4/10

Exceptional

(218)

"Love Love Love this hotel! Can’t wait to stay again! Close to everything in Salem. Super cute vibe, perfect place to stay."

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

Mindi

[](https://www.expedia.ca/Boston-Hotels-The-Bell-Inn.h96507199.Hotel-Information)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

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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.

![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Charles Hotel

One Bennett Street, Cambridge, MA

CA $334

CA $387 total

Nov 23 - Nov 24

includes taxes & fees

9.2/10 Wonderful! (1,018 reviews)

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

![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Dagny Boston

89 Broad Street, Boston, MA

CA $200

CA $282 total

Nov 30 - Dec 1

includes taxes & fees

9.4/10 Exceptional! (6,638 reviews)

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

![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hilton Boston Logan Airport

One Hotel Drive, Boston, MA

CA $194

CA $226 total

Nov 24 - Nov 25

includes taxes & fees

8.8/10 Excellent! (3,533 reviews)

[](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.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%2F11%2F2025&endDate=04%2F11%2F2025&regionId=175481&star=50)

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

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&regionId=175481&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&regionId=175481&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&regionId=175481&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&regionId=175481&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&regionId=175481&star=50&star=50&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=2025-11-16&endDate=2025-11-17&adults=2&regionId=175481)

![Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.](https://images.trvl-media.com/place/175481/b0e1353c-e076-4705-8fac-9f9c6a9d0f94.jpg?impolicy=fcrop&w=900&h=341&p=1&q=high)

## Top Winchester Hotel Reviews

![Omni Boston Hotel at the Seaport](//images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg)

### Omni Boston Hotel at the Seaport

10/10 Excellent

"Amazing service, upgrades and the in-house dining is amazing! "

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

![Encore Boston Harbor](//images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg)

### Encore Boston Harbor

10/10 Excellent

"Very nice rooms, free transportation to Bruins Games"

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

![The Langham, Boston](//images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg)

### The Langham, Boston

10/10 Excellent

"We enjoyed everything about the hotel and its location. I will be booking here again! "

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

## Find out more about Winchester

## Five Star Hotels in Winchester

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winchester so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winchester and get ready to be pampered like never before.

#### Get a Great Deal on 5-Star Hotels in Winchester

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

#### Make Your Escape to Winchester

The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winchester! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winchester today and settle down in the lap of luxury tomorrow.

## Frequently asked questions

### What are the best 5-star hotels in Winchester?

> [Encore Boston Harbour](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), [The Liberty, a Marriott Luxury Collection Hotel, Boston](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information) and [XV Beacon](https://www.expedia.ca/Boston-Hotels-Fifteen-Beacon.h201184.Hotel-Information) are among the most popular 5-star hotels in Winchester, according to our customer reviews. These swanky hotels rate highly for things such as their conveniences, location and guest services. Select your favourite and experience the best of everything.

### 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 based on when you decide to travel and how long you plan to stay, among a range of factors. Take advantage of our price per night filter and other search tools to land the best rate on a high-end getaway.
> 
>   
> 
> -   Search for the lowest price per night from CA $226

### What makes a hotel 5 stars in Winchester?

> In Winchester, a hotel must offer a certain number of upscale features to be designated 5 stars. These may include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their extraordinary service. You'll enjoy things like nightly turn-down services, in-room massages and concierge services. Some may also offer thoughtful touches like welcome gifts.

## Explore a world of travel with Expedia

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