Title: Winchester Vacation Home Rentals from CA $199: Search Top Private Vacation Homes for Rent | 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

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/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 three months

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

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-05-08&endDate=2026-05-10&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 homes

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/dc25e9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/b1817ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/3c2e9101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/39520f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3BR3Bth Entire House/Steps to Downtown & TD Garden

[](https://www.expedia.ca/Boston-Hotels-3BR3Bth-Entire-HouseSteps-To-Downtown-TD-Garden.h119591835.Hotel-Information)

North End

10/10

Exceptional

(4 reviews)

"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "

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

mary j.

CA $345

CA $818 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Boston-Hotels-3BR3Bth-Entire-HouseSteps-To-Downtown-TD-Garden.h119591835.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/fdae0986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/da72b451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/26c85723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/a1fc63d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

[](https://www.expedia.ca/Hull-Hotels-Newly-Renovated-2-Br-Apt-1-Min-Walk-To-The-Beach-King-Queen.h91883617.Hotel-Information)

Bayside

9.8/10

Exceptional

(15 reviews)

"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "

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

Candice C.

CA $236

CA $562 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Hull-Hotels-Newly-Renovated-2-Br-Apt-1-Min-Walk-To-The-Beach-King-Queen.h91883617.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/c6ab1483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/f822e23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/8e9f1637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/3634414f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gorgeous Beacon Hills Studio next to State house

[](https://www.expedia.ca/Boston-Hotels-Gorgeous-Beacon-Hills-Studio-Next-To-State-House.h66847031.Hotel-Information)

Beacon Hill

9.8/10

Exceptional

(32 reviews)

"Loved the private outdoor patio"

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

Robin P.

CA $249

CA $492 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Boston-Hotels-Gorgeous-Beacon-Hills-Studio-Next-To-State-House.h66847031.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/367fea3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/213ab480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/w4320h3285x0y3-6304351e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/6eb23938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden Gem right in the city of Boston!

[](https://www.expedia.ca/Boston-Hotels-Lovely-Apartment-In-The-City-Of-Boston.h91036903.Hotel-Information)

Hyde Park

9.6/10

Exceptional

(25 reviews)

"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."

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

TIARA V.

CA $180

CA $545 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Boston-Hotels-Lovely-Apartment-In-The-City-Of-Boston.h91036903.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/f27e1890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/0493d76f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/c9023e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/e3ad2c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*NEW Spooky Halloween |2BR|Downtown Salem|Parking

[](https://www.expedia.ca/Boston-Hotels-New-Spooky-2Br-LayerDowntownSalemFREEParking.h92713152.Hotel-Information)

Salem

9.2/10

Wonderful

(51 reviews)

"Very clean, quiet and convenient location! The owners checked in with me through the app to make sure we had everything we needed. I would stay again!"

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

Rebecca T.

CA $167

CA $394 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Boston-Hotels-New-Spooky-2Br-LayerDowntownSalemFREEParking.h92713152.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/105000000/104910000/104902800/104902706/a5896111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104910000/104902800/104902706/b978dbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/105000000/104910000/104902800/104902706/a8e937d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104910000/104902800/104902706/02693330.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nothing Fancy Older Pet Friendly Home – near I-95

[](https://www.expedia.ca/Georgetown-Hotels-Spacious-Pet-Friendly-Home-Sleeps-8-Near-I-95.h104902706.Hotel-Information)

Georgetown

9.4/10

Exceptional

(3 reviews)

"Came for a short stay and had absolutely no complaints. Easy entry, great communication and an amazing home to stay in. Would highly recommend:)"

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

Fedalis R.

CA $147

CA $418 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Georgetown-Hotels-Spacious-Pet-Friendly-Home-Sleeps-8-Near-I-95.h104902706.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/af33334c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/963cdbb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/b37b282d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/43bde42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

[](https://www.expedia.ca/Boston-Hotels-The-Sunset-Lighthouse-Marblehead-Exclusive-Waterfront-3brm25bath-Home.h109118878.Hotel-Information)

Marblehead

9.6/10

Exceptional

(15 reviews)

"Perfect location on Marblehead Neck with stunning views of the harbor. The house was just right for a family of 5 adults. We would come back and would recommend this lovely house to anyone. "

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

Debbie B.

CA $263

CA $745 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Boston-Hotels-The-Sunset-Lighthouse-Marblehead-Exclusive-Waterfront-3brm25bath-Home.h109118878.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/a9b43217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/dac5c927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/391131e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/73ef80e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom building in delightful Hull with ocean view

[](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Building-In-Delightful-Hull-With-Ocean-View.h115977790.Hotel-Information)

Nantasket Beach

9.6/10

Exceptional

(5 reviews)

"We loved the location. The apartment was clean and had everything needed. The host was responsive. We would stay here again."

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

Rebecca B.

CA $222

CA $423 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Building-In-Delightful-Hull-With-Ocean-View.h115977790.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/67c5ea68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/e71ec9fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/0e189791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/24bfbb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire 4BR 2 Bath Home l Minutes to Downtown Salem

[](https://www.expedia.ca/Boston-Hotels-Entire-4BR-2-Bath-Home-L-Minutes-To-Downtown-Salem.h108237439.Hotel-Information)

Salem

10/10

Exceptional

(18 reviews)

"Our stay was fantastic. Great location, only an 8 minute walk to Essex st. Great host as well! "

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

Adam R.

CA $196

CA $602 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Boston-Hotels-Entire-4BR-2-Bath-Home-L-Minutes-To-Downtown-Salem.h108237439.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/ea77dad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/afd662e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/fee14905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/decc6eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 bedroom's 1 bathroom 10 min-Airport/Downtown Boston 7 min-Encore Casino

[](https://www.expedia.ca/Boston-Hotels-2-Bedrooms-1-Bathroom-10-Min-AirportDowntown-Boston-7-Min-Encore-Casino.h113898567.Hotel-Information)

Everett

10/10

Exceptional

(6 reviews)

"Great neighborhood! House is beautiful and alot bigger then expected! If we ever get back to the area, this would be my first pick to stay. "

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

Danielle s.

CA $237

CA $517 total

includes taxes & fees

Feb 4 - Feb 5

[](https://www.expedia.ca/Boston-Hotels-2-Bedrooms-1-Bathroom-10-Min-AirportDowntown-Boston-7-Min-Encore-Casino.h113898567.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/77000000/76340000/76331900/76331885/w954h683x41y0-082be846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/77000000/76340000/76331900/76331885/2816d041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76340000/76331900/76331885/89bec837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76340000/76331900/76331885/w904h683x60y0-2f362e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ✨Private Studio w/ Loft Center Historic Carlisle✨

[](https://www.expedia.ca/Carlisle-Hotels-Private-Studio-W-Loft-Center-Historic-Carlisle.h76331885.Hotel-Information)

Carlisle

9.4/10

Exceptional

(33 reviews)

"Wonderful stay"

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

Brent H.

CA $91

CA $199 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Carlisle-Hotels-Private-Studio-W-Loft-Center-Historic-Carlisle.h76331885.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89350000/89348200/89348127/248bba1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/90000000/89350000/89348200/89348127/913cf74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/90000000/89350000/89348200/89348127/e01e2aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/90000000/89350000/89348200/89348127/e06ecf92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Large House close to TUFTS/Harvard/MIT 4BR

[](https://www.expedia.ca/Boston-Hotels-Cozy-Large-House-Close-To-TUFTSHarvardMIT-4BR.h89348127.Hotel-Information)

South Medford

9.6/10

Exceptional

(8 reviews)

"Very nice house check in was easy there was parking and the beds were comfortable. Shower with great water pressure and a well stocked kitchen for making and eating food! "

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

Ronan B.

CA $228

CA $678 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Boston-Hotels-Cozy-Large-House-Close-To-TUFTSHarvardMIT-4BR.h89348127.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/100000000/99780000/99774400/99774365/w933h683x46y0-a790ee23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/100000000/99780000/99774400/99774365/w904h683x60y0-2be3a691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/100000000/99780000/99774400/99774365/9ec2fbef.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/100000000/99780000/99774400/99774365/2ea674d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire Lower Level of the House, Across From The Beach

[](https://www.expedia.ca/Boston-Hotels-Entire-Lower-Level-Of-The-House.h99774365.Hotel-Information)

Swampscott

9.8/10

Exceptional

(25 reviews)

"Wonderful place! Diana was a wonderful host and provided everything we needed for a cozy stay on our girls trip!"

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

Dana F.

CA $275

CA $490 total

includes taxes & fees

Jan 24 - Jan 25

[](https://www.expedia.ca/Boston-Hotels-Entire-Lower-Level-Of-The-House.h99774365.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/5b41d148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/ab71ea45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/3b11903d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/96c81079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LUXE 4BDR/2BA Near Boston- T-Station & Encore Casino

[](https://www.expedia.ca/Boston-Hotels-LUXE-4BDR2BA-Near-Boston-T-Station-Free-Parking.h119628776.Hotel-Information)

East Somerville

10/10

Exceptional

(2 reviews)

"Great stay and host was very responsive to any questions. "

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

Matt R.

CA $140

CA $472 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Boston-Hotels-LUXE-4BDR2BA-Near-Boston-T-Station-Free-Parking.h119628776.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/52000000/51930000/51928300/51928202/eca684f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51930000/51928300/51928202/f1ac00bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/52000000/51930000/51928300/51928202/54852798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/52000000/51930000/51928300/51928202/1c90bdd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

[](https://www.expedia.ca/Boston-Hotels-Modern-Duplex-Home-Close-To-Boston-Free-Parking.h51928202.Hotel-Information)

Everett

9.4/10

Exceptional

(28 reviews)

"It worked perfect for me and my friends and was a nice distance from the city. Amenities were nice and the whole process was super easy!"

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

Brendan D.

CA $189

CA $521 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Boston-Hotels-Modern-Duplex-Home-Close-To-Boston-Free-Parking.h51928202.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/352e08d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/d5f01cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, desk, travel crib](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/3c584a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/db6adb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 383 - 3BR - Quincy Chic House near Adams Park

[](https://www.expedia.ca/Boston-Hotels-383-Spacious-NEW-Townhouse-5-Beds-3-Baths-20To-Boston.h72583807.Hotel-Information)

Quincy

9.6/10

Exceptional

(44 reviews)

"very clean. comfortable beds. Very nice stay."

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

Stefanie K.

CA $250

CA $532 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Boston-Hotels-383-Spacious-NEW-Townhouse-5-Beds-3-Baths-20To-Boston.h72583807.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122910000/122903000/122902933/ee902f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122910000/122903000/122902933/f316e35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/123000000/122910000/122903000/122902933/3561685b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122910000/122903000/122902933/601a3210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Large Bedrooms | Modern Décor | Spacious

[](https://www.expedia.ca/Boston-Hotels-3-Large-Bedrooms-Modern-Decor-Spacious.h122902933.Hotel-Information)

Everett

[](https://www.expedia.ca/Boston-Hotels-3-Large-Bedrooms-Modern-Decor-Spacious.h122902933.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92050000/92049600/92049583/w438h683x293y0-7d56ff99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92050000/92049600/92049583/w1024h491x0y96-1e284e98.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/93000000/92050000/92049600/92049583/w400h683x312y0-44cbff9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92050000/92049600/92049583/w515h683x255y0-7c5230a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Centrally located in the heart of Boston near T

[](https://www.expedia.ca/Boston-Hotels-Centrally-Located-In-The-Heart-Of-Boston-Near-T.h92049583.Hotel-Information)

Dorchester

9.0/10

Wonderful

(22 reviews)

"This was the best vacation, the owner was available to talk anytime to make my stay pleasant."

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

ADEWALE A.

CA $249

CA $627 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Boston-Hotels-Centrally-Located-In-The-Heart-Of-Boston-Near-T.h92049583.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/f46acbda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/4a680a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/5be50117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/9ef5bf05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HOLIDAY GETAWAY SPECIAL -EARLY BIRD 10% 39 - Modern 3BR Quincy near Adams

[](https://www.expedia.ca/Boston-Hotels-39-Newly-Built-Townhouse.h72583990.Hotel-Information)

Quincy

9.6/10

Exceptional

(50 reviews)

"Very clean and stay was enjoyable. "

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

Sheldon S.

CA $238

CA $515 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Boston-Hotels-39-Newly-Built-Townhouse.h72583990.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/07776021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/5145bd0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/d038ed64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/5b4932fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 37 - 3BR Quincy - Cozy Townhouse near Adams Park

[](https://www.expedia.ca/Boston-Hotels-37-Greater-Boston-Cozy-Townhouse.h72584577.Hotel-Information)

Quincy

9.2/10

Wonderful

(36 reviews)

"property was as described, very clean and remodeled. Owner was a pleasure to deal with. Would stay again in the future. "

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

Andrew A.

CA $157

CA $411 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Boston-Hotels-37-Greater-Boston-Cozy-Townhouse.h72584577.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=2026-01-30&endDate=2026-01-31&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=APART_HOTEL)

Apartments

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Private vacation homes

[](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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=VACATION_HOME)

Condos

[](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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=CONDO)

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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=COTTAGE)

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=2026-04-16&d1=2026-04-16&endDate=2026-04-19&d2=2026-04-19&lodging=HOUSE_BOAT)

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## Top Winchester Hotel Reviews

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

### Omni Parker House 

10/10 Excellent

"Yes"

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

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

### Boston Harbor Hotel

10/10 Excellent

"Beautiful and great service "

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

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

### citizenM Boston North Station

10/10 Excellent

"Very helpful and courteous staff"

[](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

"Clean and smelled good"

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

"I loved the atmosphere, it was a lovely in a great location. "

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

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

### Hyatt Regency Boston

10/10 Excellent

"Great location!!!"

[](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.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 entire facility was great. "

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

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

### The Langham, Boston

10/10 Excellent

"No complaints , everything . I would go back again and again."

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

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

### The Dagny Boston

10/10 Excellent

"Spotless room, great staff, and amazing location! "

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

## Find out more about Winchester

## Winchester Vacation Homes information

| Number of reviews | 412                |
| ----------------- | ------------------ |
| Accommodation     | 544 Vacation Homes |
| Lowest Price      | CA $199            |
| Highest Price     | CA $818            |

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