Title: Best Apartments in Winchester, MA for Your Vacation from $178 | Expedia.com

[Winchester Travel Guide](https://expedia.com/Winchester.dx175481)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d175481.Destination-Travel-Guides)

![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

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-06-19&endDate=2026-06-21&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

![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)

### Apartment in South End

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

$271 nightly

$312 total

Feb 27 - Feb 28

Total with taxes and fees

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

![1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets](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 | Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5c22409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Room | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/f8b6e982.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)

### Apartment in Downtown Boston

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

7.0/10

Good

(333 reviews)

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

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

Beiyu

$155 nightly

$178 total

Feb 27 - Feb 28

Total with taxes and fees

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

![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/e6a316f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/5458ec70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/3ecf66a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/126000000/125080000/125077200/125077200/4102425e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.com/Boston-Hotels-Boston-Financial-District-1BR-Walk-To-Anything.h125077200.Hotel-Information)

$343 nightly

$403 total

Mar 20 - Mar 21

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Boston-Financial-District-1BR-Walk-To-Anything.h125077200.Hotel-Information)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124120000/124111600/124111553/197fe0bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124120000/124111600/124111553/4e456ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124120000/124111600/124111553/595ecb90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/125000000/124120000/124111600/124111553/34ef7ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Lynn

[](https://www.expedia.com/Boston-Hotels-Apt-In-Historic-Lynn-Neighborhood-2-Mi-To-Beach.h124111553.Hotel-Information)

$278 nightly

$305 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Apt-In-Historic-Lynn-Neighborhood-2-Mi-To-Beach.h124111553.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/126000000/125080000/125074300/125074227/cc595245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125080000/125074300/125074227/92a4145e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125074300/125074227/5684df26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/126000000/125080000/125074300/125074227/d2cb8d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fenway–Kenmore

[](https://www.expedia.com/Boston-Hotels-Luxury-Home-Located-In-Back-Bay-8min-Walk-To-Fewnway-Park.h125074227.Hotel-Information)

10/10

Exceptional

(1 review)

$297 nightly

$349 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Luxury-Home-Located-In-Back-Bay-8min-Walk-To-Fewnway-Park.h125074227.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/104000000/103110000/103106200/103106122/31b86770.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)

![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)

### Apartment in Downtown Boston

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

8.6/10

Excellent

(18 reviews)

"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "

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

elena d.

$198 nightly

$233 total

Feb 27 - Feb 28

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/126000000/125080000/125073400/125073362/f3b84fa3_edited_b6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/126000000/125080000/125073400/125073362/bf86b377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125073400/125073362/75a07fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125080000/125073400/125073362/622e658c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Downtown Boston

[](https://www.expedia.com/Boston-Hotels-Steps-To-North-End.h125073362.Hotel-Information)

$223 nightly

$263 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Steps-To-North-End.h125073362.Hotel-Information)

![Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/126000000/125190000/125180800/125180791/655986cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/126000000/125190000/125180800/125180791/d0d85b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125190000/125180800/125180791/9af6544a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125190000/125180800/125180791/6893bd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Back Bay

[](https://www.expedia.com/Boston-Hotels-South-End-Serene-Studio.h125180791.Hotel-Information)

$214 nightly

$248 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-South-End-Serene-Studio.h125180791.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/78000000/77820000/77813500/77813434/320321a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77820000/77813500/77813434/450b0d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/78000000/77820000/77813500/77813434/bb661fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77820000/77813500/77813434/196f1b47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North End

[](https://www.expedia.com/Boston-Hotels-Prime-Central-1brm-In-North-End-Boston.h77813434.Hotel-Information)

9.6/10

Exceptional

(25 reviews)

"Location was ideal and property was well-kept and organized. Definitely would recommend for future visits."

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

Taye A.

$320 nightly

$368 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Prime-Central-1brm-In-North-End-Boston.h77813434.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112070000/112063900/112063888/5269ceab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112070000/112063900/112063888/0fd71ac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/113000000/112070000/112063900/112063888/ba8e9089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112070000/112063900/112063888/58d4369c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fenway–Kenmore

[](https://www.expedia.com/Boston-Hotels-Free-Parking-At-1-Bed-Basement-Apt.h112063888.Hotel-Information)

7.8/10

Good

(8 reviews)

"This location is so convenient to BU! Loved how easy check-in was!"

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

Laura B.

$198 nightly

$216 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Free-Parking-At-1-Bed-Basement-Apt.h112063888.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119900000/119895400/119895385/be752f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119900000/119895400/119895385/e1eb08b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119900000/119895400/119895385/a0c68c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/120000000/119900000/119895400/119895385/96b7e2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Salem

[](https://www.expedia.com/Enchanting-2-Bedroom-Apartment-In-Salem-Near-Attractions.h119895385.Hotel-Information)

10/10

Exceptional

(5 reviews)

"Great property!!!"

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

Heather

$255 nightly

$285 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Enchanting-2-Bedroom-Apartment-In-Salem-Near-Attractions.h119895385.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/120000000/119850000/119844400/119844387/00e40c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119850000/119844400/119844387/bb9918ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119850000/119844400/119844387/c41ddb8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/120000000/119850000/119844400/119844387/698e35c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in North End

[](https://www.expedia.com/Boston-Hotels-North-End-Entire-House.h119844387.Hotel-Information)

10/10

Exceptional

(16 reviews)

"Great location in the Northend!"

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

Carol T.

$439 nightly

$504 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-North-End-Entire-House.h119844387.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)

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

![TV](https://images.trvl-media.com/lodging/113000000/112590000/112585100/112585043/1693fc21.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)

### Apartment in Back Bay

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

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

$277 nightly

$298 total

Mar 2 - Mar 3

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/94000000/93330000/93320800/93320764/46ce0088.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)

![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.com/Boston-Hotels-Artful-Escape-Minutes-To-Salem.h93320764.Hotel-Information)

9.0/10

Wonderful

(22 reviews)

"Cheerful decor, well-equipped kitchen, and clean. Good location in walking distance to restaurants. However, there was a musty smell throughout the building and rooms. "

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

Julia

$263 nightly

$294 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Artful-Escape-Minutes-To-Salem.h93320764.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)

![Smart TV, books](https://images.trvl-media.com/lodging/100000000/99920000/99916000/99915917/w506h683x259y0-b22b9397.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.com/Boston-Hotels-Bright-2BR-By-Boston-Waterfront.h99915917.Hotel-Information)

9.8/10

Exceptional

(15 reviews)

"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

$211 nightly

$243 total

Feb 27 - Feb 28

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/114000000/113270000/113261000/113260976/916b6a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113270000/113261000/113260976/d0d20c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113270000/113261000/113260976/e888f225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/114000000/113270000/113261000/113260976/bfebb442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Salem

[](https://www.expedia.com/Boston-Hotels-Central-Salem-Retreat-2bd-W-Parking.h113260976.Hotel-Information)

9.2/10

Wonderful

(15 reviews)

"It was very clean, a great location, and the host was super responsive and helpful!"

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

Kristen N.

$199 nightly

$202 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Central-Salem-Retreat-2bd-W-Parking.h113260976.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)

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

![Basic Room (2nd Floor - #209) | Individually furnished, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/6615076a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fenway–Kenmore

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

8.6/10

Excellent

(337 reviews)

"Good place"

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

Elijah

$190 nightly

$218 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-28-Fenway.h95348090.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/73000000/72690000/72689800/72689792/0f920cc5.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.com/Boston-Hotels-Cozy-Studio-Steps-From-Boston-Common-And-Theaters.h72689792.Hotel-Information)

7.4/10

Good

(10 reviews)

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

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

Laurie F.

$227 nightly

$267 total

Feb 28 - Mar 1

Total with taxes and fees

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

![TV](https://images.trvl-media.com/lodging/118000000/117920000/117919400/117919316/c62f8a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117919400/117919316/7978c1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117919400/117919316/89a6c1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117919400/117919316/ff60699d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Beverly

[](https://www.expedia.com/Boston-Hotels-Dwtn-AptKing-BedsMins-To-Salem.h117919316.Hotel-Information)

8.4/10

Very Good

(9 reviews)

"Christian was a great host. The apartment was in a great location and was very comfortable. We had a great stay and would definitely recommend this place if you are visiting the Beverly/Salem area! "

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

Jennifer C.

$250 nightly

$267 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Dwtn-AptKing-BedsMins-To-Salem.h117919316.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)

![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)

![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/ba77e7a0.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)

### Apartment in Downtown Boston

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

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.

$245 nightly

$288 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.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.com/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=APARTMENT)

Private vacation homes

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Condos

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Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-27&d1=2026-05-27&endDate=2026-05-30&d2=2026-05-30&lodging=COTTAGE)

Houseboats

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## Top Winchester Hotel Reviews

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

### The Dagny Boston

10/10 Excellent

"Loved the black out curtains. No light snuck in"

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

![YOTEL Boston](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311_y.jpg)

### YOTEL Boston

10/10 Excellent

"The staff, valet, bartender and cute little room was perfect! "

[](https://expedia.com/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information)

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

### Seaport Hotel Boston

10/10 Excellent

"Very helpful and kind staff. Clean rooms and comfy beds. Will stay again!"

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

![The Lenox Hotel Boston](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/db068914_y.jpg)

### The Lenox Hotel Boston

10/10 Excellent

"Clean room, staff, restaurant at breakfast, wi-fi connection"

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

![Copley Square Hotel, a FOUND Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881_y.jpg)

### Copley Square Hotel, a FOUND Hotel

10/10 Excellent

"Wverything was OK. Quiet & nice place, clean bedsheets & towels."

[](https://expedia.com/Boston-Hotels-Copley-Square-Hotel.h16067.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

"Room spotless and staff was courteous "

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

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

### Hyatt Regency Boston

10/10 Excellent

"Had a nice stay. Front desk staff was very pleasant! "

[](https://expedia.com/Boston-Hotels-Hyatt-Regency-Boston.h17845.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

"Great staff"

[](https://expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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

"Always great. Coffee shop options could be better for early morning flights."

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

## Find out more about Winchester

## Winchester Apartments information

| Number of reviews | 783             |
| ----------------- | --------------- |
| Accommodation     | 1996 Apartments |
| Lowest Price      | $178            |
| Highest Price     | $504            |

## 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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