Title: Winchester Vacation Rentals from CA $191: Short-Term Rentals for 2026 | 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 prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation rentals

![Lobby lounge](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/a3189863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Studio | Private kitchen](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/62688d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/8bc05b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/6a31a5cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Global Luxury Suites Downtown Boston

[](https://www.expedia.ca/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information)

Chinatown

8.0/10

Very good

(656 reviews)

"Everything was great about this place! I will definitely be staying here again!"

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

Amanda

CA $115

CA $194 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information)

![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/f70f107d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/b309a2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/bbc07a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/6bdc1239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 400 Columbus Ave

[](https://www.expedia.ca/Boston-Hotels-400-Columbus-Avenue.h88179829.Hotel-Information)

South End

7.2/10

Good

(135 reviews)

"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"

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

Maelynn

CA $130

CA $275 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Boston-Hotels-400-Columbus-Avenue.h88179829.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/2e7614de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/978ddac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/90989604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/7f1f7cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 245 Newbury St

[](https://www.expedia.ca/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information)

Back Bay

8.2/10

Very good

(157 reviews)

"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "

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

Steven

[](https://www.expedia.ca/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information)

![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)

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

![Deluxe Apartment, 1 Double Bed with Sofa bed | Private kitchen](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/342a0357.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)

### Temple Place Suites

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

Downtown Boston

7.0/10

Good

(331 reviews)

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

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

Beiyu

CA $112

CA $215 total

includes taxes & fees

Feb 8 - Feb 9

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

![Front of property](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/0dd63623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio (Unit 7)](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/2fc6bbd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio (Unit 7) | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/44b2972c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/05b3d150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 40 Temple St

[](https://www.expedia.ca/Boston-Hotels-40-Temple-St.h89660519.Hotel-Information)

Beacon Hill

7.6/10

Good

(103 reviews)

"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"

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

Jordan Elizabeth Marie

[](https://www.expedia.ca/Boston-Hotels-40-Temple-St.h89660519.Hotel-Information)

![Deluxe Double Room, Shared Bathroom](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w851h480x0y0-8b426c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w837h480x0y0-3c5d7594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w843h480x0y0-ebedf864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | Living area](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/1df69efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premier Suites - Bay Village

[](https://www.expedia.ca/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.Hotel-Information)

Bay Village

6.2/10

(257 reviews)

"We stayed there for four days. The heaters were not working, I got almost sick. And the customer service was awful. I hope you will find better place to stay"

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

Aziza

CA $105

CA $191 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.Hotel-Information)

![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/55a7f850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/aa08e294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/41f2434e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/7e78cb5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bay Village Suites

[](https://www.expedia.ca/Boston-Hotels-Rooms-At-Premier-Suites-Bay-Village.h92422919.Hotel-Information)

Bay Village

6.6/10

(253 reviews)

"Great location nice neighborhood "

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

Jose

CA $105

CA $191 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Boston-Hotels-Rooms-At-Premier-Suites-Bay-Village.h92422919.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)

![Basic Room (2nd Floor - #209)](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/6615076a.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)

### Maverick Suites at 28 Fenway

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

Fenway–Kenmore

8.6/10

Excellent

(337 reviews)

"Good place"

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

Elijah

CA $129

CA $282 total

includes taxes & fees

Feb 8 - Feb 9

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

![Interior entrance](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/41817f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/994122c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/08d8edd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/37cdd40c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 89 Marion

[](https://www.expedia.ca/Boston-Hotels-89-Marion.h89420220.Hotel-Information)

Coolidge Corner South Side

8.2/10

Very good

(271 reviews)

"The room was very clean and perfectly sized for a solo traveler for several nights."

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

Valeri

CA $126

CA $262 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Boston-Hotels-89-Marion.h89420220.Hotel-Information)

![Premium Studio Suite](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/ffbbd281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/285a83d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Studio Suite](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/1327e38c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Studio | Living area](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/12d64f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charlesgate Suites

[](https://www.expedia.ca/Boston-Hotels-The-Gryphon-House.h22214064.Hotel-Information)

Fenway–Kenmore

9.4/10

Exceptional

(201 reviews)

"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"

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

Brian

CA $208

CA $475 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Boston-Hotels-The-Gryphon-House.h22214064.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/df58d6c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/c6f34a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/f1c20571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/7e7f55b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Crescent Suites Hotel

[](https://www.expedia.ca/Boston-Hotels-Crescent-Suites-Hotel.h2673422.Hotel-Information)

South Side

9.6/10

Exceptional

(1,151 reviews)

"Everything about this facility was pleasing: clean, well-appointed, great kitchen, comfortable, well-located in the area. We were given a warm welcome when we arrived, provided with lots of information about Waltham. Located near shops and restaurants and on a walking trail along the Charles River. Highly recommend and would stay here again. "

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

Susan

[](https://www.expedia.ca/Boston-Hotels-Crescent-Suites-Hotel.h2673422.Hotel-Information)

![Luxury Suite 2 | Living area](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/040aa257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite | Living area](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/0e47251d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, Egyptian cotton sheets, premium bedding, minibar](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/7363ccac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/57a8e10a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Monty Boston

[](https://www.expedia.ca/Boston-Hotels-The-Monty-Boston.h103772852.Hotel-Information)

Downtown Boston

9.6/10

Exceptional

(32 reviews)

"Amazing property, would stay again."

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

Doug

CA $697

CA $1,038 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Boston-Hotels-The-Monty-Boston.h103772852.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/cbb3b9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/f964d018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/b61106da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/07b376b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maverick Suites at 402 Columbus Ave

[](https://www.expedia.ca/Boston-Hotels-402-Columbus-Ave.h78422939.Hotel-Information)

South End

8.0/10

Very good

(69 reviews)

"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "

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

Isaiah Joel Santa

[](https://www.expedia.ca/Boston-Hotels-402-Columbus-Ave.h78422939.Hotel-Information)

![Apartment, 2 Bedrooms | Interior](https://images.trvl-media.com/lodging/125000000/124400000/124390600/124390547/c5a347c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms | Interior](https://images.trvl-media.com/lodging/125000000/124400000/124390600/124390547/dd8f16a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms | Interior](https://images.trvl-media.com/lodging/125000000/124400000/124390600/124390547/8b21e961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 2 Bedrooms | Interior](https://images.trvl-media.com/lodging/125000000/124400000/124390600/124390547/fe7b7432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished Apartment near BMC

[](https://www.expedia.ca/Boston-Hotels-Furnished-Apartment-Near-BMC.h124390547.Hotel-Information)

South End

CA $128

CA $337 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Boston-Hotels-Furnished-Apartment-Near-BMC.h124390547.Hotel-Information)

![Premium Apartment | Living area](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/2d8ce635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/w1438h1080x242y0-a59fde2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/677325f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/e514eb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Chester Hotel

[](https://www.expedia.ca/Boston-Hotels-The-Chester.h105955992.Hotel-Information)

South End

8.6/10

Excellent

(28 reviews)

"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "

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

kelly

CA $212

CA $487 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Boston-Hotels-The-Chester.h105955992.Hotel-Information)

![Indoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/c68f569b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/742d229a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/eef404cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/606054a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Global Luxury Suites East Boston

[](https://www.expedia.ca/Boston-Hotels-Global-Luxury-Suites-East-Boston.h59296491.Hotel-Information)

East Boston

7.0/10

Good

(179 reviews)

"The place was very nice and nicely equipped, but a little difficult to locate."

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

William

CA $113

CA $191 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Boston-Hotels-Global-Luxury-Suites-East-Boston.h59296491.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)

![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)

![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/31b86770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect One Bedroom Stay In Downtown Boston!

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

Downtown Boston

8.6/10

Excellent

(18 reviews)

"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 $134

CA $284 total

includes taxes & fees

Feb 8 - Feb 9

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

![Marina](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/d74eb2f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/3bde57f2.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/38000000/37290000/37280700/37280691/00ab78a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/38000000/37290000/37280700/37280691/31e3bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charlestown Houseboat Walk to attractions Be rocked to sleep

[](https://www.expedia.ca/Boston-Hotels-Charlestown-Houseboat-Walk-To-Attractions-Be-Rocked-To-Sleep.h37280691.Hotel-Information)

Thompson Square - Bunker Hill

9.6/10

Exceptional

(99 reviews)

"Responsive host, amazing location, and refreshing change from a brick and mortar. "

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

Larry N.

CA $82

CA $530 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Boston-Hotels-Charlestown-Houseboat-Walk-To-Attractions-Be-Rocked-To-Sleep.h37280691.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/98fb199d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/d112c10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/e687838b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/e1889f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Come Visit Boston and Stay In Our Homey Studio

[](https://www.expedia.ca/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.Hotel-Information)

Downtown Boston

8.8/10

Excellent

(3 reviews)

"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"

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

Dean and Courtenay M.

CA $134

CA $286 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.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)

### Stylish Back Bay Retreat, Steps from Prudential

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

Back Bay

8.6/10

Excellent

(7 reviews)

"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 $167

CA $406 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Boston-Hotels-Stylish-Back-Bay-Retreat.h112585043.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=2026-02-21&endDate=2026-02-22&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Apartments

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Aparthotels

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Condos

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=HOUSE_BOAT)

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## Top Winchester Hotel Reviews

![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg)

### The Godfrey Hotel Boston

10/10 Excellent

"The staff was extremely friendly and accommodating. The decor was beautiful. The room was very clean and comfortable. "

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

"Best price for the location! Always clean and great staff!"

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

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

### Encore Boston Harbor

10/10 Excellent

"Wonderful service, gorgeous room"

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

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

### Seaport Hotel Boston

10/10 Excellent

"Beautiful hotel, excellent staff and really nice location."

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

"Clean and comfortable, great view of the city and airplanes on approach to landing. "

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

"Clean room. Great staff!"

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

"The room looked amazing and the staff was very nice"

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

![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg)

### Omni Parker House 

10/10 Excellent

"Clean room, classy service, valet and bellhops were awesome!"

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

![Hyatt Place Boston/Seaport District](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844_y.jpg)

### Hyatt Place Boston/Seaport District

10/10 Excellent

"Location was great! Very clean and friendly staff!"

[](https://expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information)

## Find out more about Winchester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d175481-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d175481-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.ca/Winchester-Condos.d175481-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d175481-aaCottages.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d175481-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Winchester ](https://expedia.ca/Winchester-Apart-Hotels.d175481-aaApartHotels.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.ca/Winchester-Guest-Houses.d175481-aaGuestHouses.Travel-Guide-Accommodation)
- [Houseboats in Winchester ](https://expedia.ca/Winchester-Houseboats.d175481-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d175481-aaMotels.Travel-Guide-Accommodation)
- [Hostels in Winchester ](https://expedia.ca/Winchester-Hostels.d175481-aaHostels.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d175481-aaInns.Travel-Guide-Accommodation)
- [Villas in Winchester ](https://expedia.ca/Winchester-Villas.d175481-aaVillas.Travel-Guide-Accommodation)
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- [Residences in Winchester ](https://expedia.ca/Winchester-Residences.d175481-aaResidences.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winchester?

### What are some of the best vacation home rentals in Winchester?

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