Title: Winchester Apartment Rentals from CA $230 | 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)

# Search Apartment Rentals in Winchester

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## Check prices for these dates

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester apartments

![1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/c0328429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment | Private kitchen](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5c22409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/f74aa0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/f8b6e982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.ca/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information)

7.0/10

Good

(326)

"Pretty clean room, good location, resonable price."

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

Beiyu

CA $124

CA $230 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/b68b988b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/2ec5ebb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/5e51303d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/w6052h4023x0y0-a9f7e4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fenway–Kenmore

[](https://www.expedia.ca/Boston-Hotels-28-Fenway.h95348090.Hotel-Information)

8.8/10

Excellent

(326)

"Good place"

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

Elijah

CA $121

CA $274 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Boston-Hotels-28-Fenway.h95348090.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/38511c45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/c7e28698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/3f43290a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/975d5cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.ca/Boston-Hotels-Best-Location-Studio-In-Downtown-Boston.h89806138.Hotel-Information)

10/10

Exceptional

(1)

"In town to celebrate a special event."

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

Pam P.

CA $143

CA $296 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Best-Location-Studio-In-Downtown-Boston.h89806138.Hotel-Information)

![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1432h1080x244y0-f97316a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1434h1080x243y0-21b78398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1436h1080x242y0-11762616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1444h1080x232y0-97adc8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in South End

[](https://www.expedia.ca/Boston-Hotels-The-Chester-Urban-Chic-Retreat-In-South-End.h106214509.Hotel-Information)

10/10

Exceptional

(1)

"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"

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

Chad T.

CA $241

CA $518 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Boston-Hotels-The-Chester-Urban-Chic-Retreat-In-South-End.h106214509.Hotel-Information)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/fcd59daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/w2038h1354x0y3-663218a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/8c3d4e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/fb107481.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North End

[](https://www.expedia.ca/Boston-Hotels-Modern-North-End-Studio.h92502721.Hotel-Information)

9.0/10

Wonderful

(10)

"Convenient location. Great restaurants. Perfect apatment for a couple. "

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

Holly V.

CA $171

CA $431 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Boston-Hotels-Modern-North-End-Studio.h92502721.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/be1b485a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/4fac5973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/bd2a722e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/8f14882d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Beacon Hill

[](https://www.expedia.ca/Boston-Hotels-Walk-To-Boston-Common.h92364708.Hotel-Information)

7.2/10

Good

(17)

"Property was excellent. Transportation was easy and communication with host was great. Thanks for a great vacation in beautiful Boston."

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

john

CA $139

CA $402 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Boston-Hotels-Walk-To-Boston-Common.h92364708.Hotel-Information)

![1 bedroom, desk, iron/ironing board, internet](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/14bf0e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/810b1ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/1b9fdaf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/1cca5427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bay Village

[](https://www.expedia.ca/Boston-Hotels-Cozy-Studio-Steps-From-Boston-Common-And-Theaters.h72689792.Hotel-Information)

7.4/10

Good

(10)

"Was clean and the location was perfect for my stay. "

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

Laurie F.

CA $85

CA $334 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Cozy-Studio-Steps-From-Boston-Common-And-Theaters.h72689792.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/w719h480x0y0-36cdd484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, shampoo](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/5861dbb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/w717h480x0y0-00e1c4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, shampoo](https://images.trvl-media.com/lodging/104000000/103120000/103113300/103113299/5f4c66aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bay Village

[](https://www.expedia.ca/Boston-Hotels-Studio-Awaits-Your-Next-Stay.h103113299.Hotel-Information)

9.2/10

Wonderful

(5)

"Would stay again"

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

mark p.

CA $143

CA $296 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Studio-Awaits-Your-Next-Stay.h103113299.Hotel-Information)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/2be0a8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/bab50deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/62b779f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/d04e748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.ca/Boston-Hotels-Perfect-One-Bedroom-Stay-In-Downtown-Boston.h103106122.Hotel-Information)

8.6/10

Excellent

(17)

"Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!"

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

Christine

CA $147

CA $301 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Perfect-One-Bedroom-Stay-In-Downtown-Boston.h103106122.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/90000000/89790000/89789600/89789573/7b032654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/90000000/89790000/89789600/89789573/c749dd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89790000/89789600/89789573/c56328e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89790000/89789600/89789573/f6557435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.ca/Boston-Hotels-Experience-Boston-At-Its-Finest.h89789573.Hotel-Information)

7.6/10

Good

(15)

"Great Location"

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

Keith R.

CA $147

CA $316 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Experience-Boston-At-Its-Finest.h89789573.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/bcf61f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/b1c18589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/c07cefd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/d4789d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North End

[](https://www.expedia.ca/Boston-Hotels-Perfetto-North-End-1brm.h102363922.Hotel-Information)

10/10

Exceptional

(11)

"The location was perfect - we would stay here again.The description and pictures are accurate."

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

Kenna E.

CA $200

CA $483 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Boston-Hotels-Perfetto-North-End-1brm.h102363922.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/4a64bb40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/7b30d7b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/0b34bd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, memory foam beds, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/31838c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.ca/Boston-Hotels-King-Bed-Loft-In-The-Heart-Of-Downtown-Boston.h73124640.Hotel-Information)

10/10

Exceptional

(37)

"It was my first time staying here, and the room was very clean and fresh. The staff were extremely friendly and helpful, and the facilities were perfect. I will definitely stay here again, and I highly recommend it to anyone."

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

MINEKI

CA $247

CA $516 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Boston-Hotels-King-Bed-Loft-In-The-Heart-Of-Downtown-Boston.h73124640.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/114000000/113740000/113739600/113739581/124cb91e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113740000/113739600/113739581/cfbf82e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/114000000/113740000/113739600/113739581/e7b6f0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113740000/113739600/113739581/f963bd31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North End

[](https://www.expedia.ca/Boston-Hotels-Prima-North-End-2brm.h113739581.Hotel-Information)

9.0/10

Wonderful

(2)

"Walking distance to TD Garden, North Station, and many great shops! Clean, quiet street. easy check in"

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

Jessica U.

CA $248

CA $572 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Boston-Hotels-Prima-North-End-2brm.h113739581.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/100000000/99920000/99916000/99915917/w906h683x59y0-9ba77c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99920000/99916000/99915917/w1020h683x4y0-76e0300e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99920000/99916000/99915917/1d7241b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99920000/99916000/99915917/d740bdbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in East Boston

[](https://www.expedia.ca/Boston-Hotels-Bright-2BR-By-Boston-Waterfront.h99915917.Hotel-Information)

10/10

Exceptional

(12)

"Great location, clean and comfortable! Even though they were traveling overseas they were very responsive....would stay there again...."

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

L

CA $127

CA $335 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Boston-Hotels-Bright-2BR-By-Boston-Waterfront.h99915917.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806500/89806401/baec2dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89810000/89806500/89806401/cc867fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806500/89806401/c8ea29a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806500/89806401/w843h480x0y0-9d485bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Bay Village

[](https://www.expedia.ca/Boston-Hotels-Perfect-Location-Sleeps-3.h89806401.Hotel-Information)

7.8/10

Good

(12)

"This location was exactly what we were looking for. Super close to the major sights for walking and close enough to hop on the T if needed. Great place to stay!"

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

Breanna R.

CA $147

CA $296 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Perfect-Location-Sleeps-3.h89806401.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/dd841a53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/2c546fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/3228b3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/w1081h822x18y0-a5c5c4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Back Bay

[](https://www.expedia.ca/Boston-Hotels-Stylish-Back-Bay-Retreat.h112585043.Hotel-Information)

8.6/10

Excellent

(7)

"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."

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

JEANPAUL

CA $168

CA $404 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Stylish-Back-Bay-Retreat.h112585043.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115930000/115923800/115923718/3a6cd551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115930000/115923800/115923718/3a150de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/116000000/115930000/115923800/115923718/e233cb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/116000000/115930000/115923800/115923718/83f05108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Salem

[](https://www.expedia.ca/Boston-Hotels-Spacious-3BDR4Bed-Apartment-With-King-Queen-Beds.h115923718.Hotel-Information)

10/10

Exceptional

(2)

"Amazing place to stay. Lots of room and very clean."

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

A S.

CA $114

CA $375 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Boston-Hotels-Spacious-3BDR4Bed-Apartment-With-King-Queen-Beds.h115923718.Hotel-Information)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/101000000/100430000/100424100/100424010/1e4d65da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/101000000/100430000/100424100/100424010/a57f4d4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/101000000/100430000/100424100/100424010/8e870985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Front of property](https://images.trvl-media.com/lodging/101000000/100430000/100424100/100424010/a8322106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Salem

[](https://www.expedia.ca/Boston-Hotels-Salem-Vacation-Rental-1-Mi-To-Downtown.h100424010.Hotel-Information)

10/10

Exceptional

(2)

"Great overall stay! "

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

Tessa

CA $160

CA $454 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Boston-Hotels-Salem-Vacation-Rental-1-Mi-To-Downtown.h100424010.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40230000/40226000/40225928/5289c813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/41000000/40230000/40226000/40225928/4603bd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40230000/40226000/40225928/ddd1ba4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/41000000/40230000/40226000/40225928/b5a0f7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Beacon Hill

[](https://www.expedia.ca/Boston-Hotels-Central-Boston-Beacon-Hill-2brm.h40225928.Hotel-Information)

9.2/10

Wonderful

(21)

"Ideal location for a quick overnight visit—nestled right in Beacon Hill, just a short stroll from shops, restaurants, and the beautiful Charles River. A convenient and charming base for exploring the area."

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

Susan Q.

CA $248

CA $562 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Boston-Hotels-Central-Boston-Beacon-Hill-2brm.h40225928.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/94000000/93330000/93320800/93320764/25302bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/94000000/93330000/93320800/93320764/a49ac9dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93330000/93320800/93320764/40fc7666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/94000000/93330000/93320800/93320764/f8cd47df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Beverly

[](https://www.expedia.ca/Beverly-Hotels-NEW-2BR-Downtown-Beverly-Artists-Escape.h93320764.Hotel-Information)

9.4/10

Exceptional

(20)

"So comfortable, clean, and cozy. Remarkably central location and really thoughtful touches throughout the apartment. We traveled with our toddler and it was super friendly space for our family. We will be back again!"

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

Rachel B.

CA $129

CA $389 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Beverly-Hotels-NEW-2BR-Downtown-Beverly-Artists-Escape.h93320764.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-29&endDate=2025-12-30&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Winchester Hotel Reviews

![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg)

### citizenM Boston North Station

10/10 Excellent

"Beautiful view! Clean. Convenient location "

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

![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg)

### The Revolution Hotel

10/10 Excellent

"Good"

[](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information)

![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg)

### Hyatt Regency Boston

10/10 Excellent

"Excellent spa"

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

![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg)

### Hilton Boston Back Bay

10/10 Excellent

"The hotel is undergoing renovations which will be an exciting improvement. Still a great staff and excellent location. Will return! "

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

![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg)

### Boston Harbor Hotel

10/10 Excellent

"Yes"

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

![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg)

### Hilton Boston Logan Airport

10/10 Excellent

"It’s very convenient when you have an early flight in the am. "

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

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

### Omni Boston Hotel at the Seaport

10/10 Excellent

"."

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

![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg)

### citizenM Boston Back Bay

10/10 Excellent

"We had a great stay. The location was perfect, bed was super comfy and bar area great to rewind in at the end of the day."

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

![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg)

### Harborside Inn Of Boston

10/10 Excellent

"The staff was very friendly and helpful. There is a restaurant connected to the hotel. Food and staff there were excellent "

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

## Find out more about Winchester

## Winchester Apartments information

| Number of reviews | 809             |
| ----------------- | --------------- |
| Accommodation     | 1996 Apartments |
| Lowest Price      | CA $230         |
| Highest Price     | CA $572         |

## Frequently asked questions

### What's it like to stay at an apartment in Winchester?

### Why choose apartments instead of traditional hotels?

### What's the best apartment I should consider for a stay in Winchester?

### What can I expect from the weather in Winchester?

### What should I see and do in Winchester?

### What's the best way to get to and around Winchester?

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