Title: Winchester Vacation Home Rentals from CA $362: 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

[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 two months

[Apr 24 - Apr 26](https://www.expedia.ca/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.ca/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.ca/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 vacation homes

![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/db6adb3e.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/39b46e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

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

9.6/10

Exceptional

(45 reviews)

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

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

Stefanie K.

CA $136

CA $383 total

includes taxes & fees

Feb 26 - Feb 27

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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/2b2035e6.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)

### Vacation Home in Hyde Park

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

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 $110

CA $449 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Boston-Hotels-Lovely-Apartment-In-The-City-Of-Boston.h91036903.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/92000000/91890000/91883700/91883617/18f16ab1.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)

### Vacation Home in Bayside

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

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 $233

CA $556 total

includes taxes & fees

Feb 26 - Feb 27

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

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

![Interior](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/4c656016.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)

### Vacation Home in Quincy

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

9.2/10

Wonderful

(36 reviews)

"Enjoyed our stay. Clean and comfortable"

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

maureen g.

CA $136

CA $383 total

includes taxes & fees

Feb 26 - Feb 27

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

![On the beach](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/b03d6289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/f27e1890.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)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/93000000/92720000/92713200/92713152/bf9d7f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Salem

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

9.2/10

Wonderful

(51 reviews)

"Cute place! Perfect size for our group of 3 adults. Kitchen was nicely equiped. Everything is within walking distance from the house. The cons of this house are the small bathrooms and the upstairs neighbors can be heard all hours of the day and night."

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

Shannon S.

CA $142

CA $362 total

includes taxes & fees

Feb 25 - Feb 26

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

![TV](https://images.trvl-media.com/lodging/96000000/95480000/95470400/95470379/w904h683x60y0-9bd57846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95480000/95470400/95470379/w505h683x260y0-7adb1468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95480000/95470400/95470379/w903h683x60y0-e340a629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95480000/95470400/95470379/w508h683x258y0-a8fa3b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Ward Two

[](https://www.expedia.ca/Boston-Hotels-Boston-2Bd-Kg-Qn-Bds-Entire-Unshared-Space-Near-Harvard.h95470379.Hotel-Information)

9.8/10

Exceptional

(12 reviews)

"Nice visit"

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

Nate P.

CA $181

CA $487 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Boston-Hotels-Boston-2Bd-Kg-Qn-Bds-Entire-Unshared-Space-Near-Harvard.h95470379.Hotel-Information)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/ad69d0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/8d910532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/ff7cf345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/89000000/88190000/88181300/88181254/05cf438c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North Braintree

[](https://www.expedia.ca/Boston-Hotels-Cozy-Three-Bedroom-Home-Close-To-Boston-W-Plenty-Of-Parking.h88181254.Hotel-Information)

10/10

Exceptional

(44 reviews)

"The house was just what we needed and the stay was super simple. "

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

Chris B.

CA $238

CA $581 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Boston-Hotels-Cozy-Three-Bedroom-Home-Close-To-Boston-W-Plenty-Of-Parking.h88181254.Hotel-Information)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123650000/123640200/123640177/7696ecb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123650000/123640200/123640177/e843ec80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123650000/123640200/123640177/bc3977f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123650000/123640200/123640177/e7e51617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dorchester

[](https://www.expedia.ca/Boston-Hotels-Modern-Boston-Stay.h123640177.Hotel-Information)

CA $115

CA $164 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Boston-Hotels-Modern-Boston-Stay.h123640177.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/100000000/99780000/99774400/99774365/9ec2fbef.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)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99780000/99774400/99774365/061dae40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Swampscott

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

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 $271

CA $485 total

includes taxes & fees

Feb 25 - Feb 26

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

![Smart TV](https://images.trvl-media.com/lodging/73000000/72590000/72584400/72584327/55e8594b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72590000/72584400/72584327/ed57aa12.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/73000000/72590000/72584400/72584327/2b89c9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/73000000/72590000/72584400/72584327/3cde1e58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

[](https://www.expedia.ca/Boston-Hotels-41-Convenient-Townhouse-With-3-Bedrooms.h72584327.Hotel-Information)

9.4/10

Exceptional

(26 reviews)

"We enjoyed our stay at this place. Comfortable and plenty of space for us."

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

Jeff L.

CA $195

CA $460 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Boston-Hotels-41-Convenient-Townhouse-With-3-Bedrooms.h72584327.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)

![Private kitchen](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/73ef80e5.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)

![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)

### Vacation Home in Nantasket Beach

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

9.6/10

Exceptional

(5 reviews)

"Stayed with family for a wedding reception close by. Location is outstanding. Walkable to all the beach restaurants and beach. "

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

Sarah S.

CA $301

CA $521 total

includes taxes & fees

Mar 17 - Mar 18

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

![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)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/cf94f7fb.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)

### Vacation Home in North End

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

10/10

Exceptional

(5 reviews)

"Clean and bright throughout, host was great with timely responses to all inquiries. Maybe not the best for young children bc of the all the stairs (which are beautiful btw)."

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

Margaret S.

CA $266

CA $710 total

includes taxes & fees

Mar 5 - Mar 6

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

![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)

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

### Vacation Home in Beacon Hill

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

9.8/10

Exceptional

(33 reviews)

"Loved the private outdoor patio"

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

Robin P.

CA $286

CA $538 total

includes taxes & fees

Mar 22 - Mar 23

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

![Fridge, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/101000000/100640000/100634300/100634230/87b113bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100640000/100634300/100634230/0a60c5fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/101000000/100640000/100634300/100634230/ba69264a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100640000/100634300/100634230/995eafbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Everett

[](https://www.expedia.ca/Boston-Hotels-PEACEFUL-CHARM-Humble-Luxury-Minutes-From-Boston.h100634230.Hotel-Information)

9.2/10

Wonderful

(5 reviews)

"Barry was just the best. Great communication. Lovely home. Described just as listed maybe even nicer. We enjoyed our stay. Pretty close to everything. Thank you for sharing your home with us! "

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

sarah J.

CA $236

CA $446 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Boston-Hotels-PEACEFUL-CHARM-Humble-Luxury-Minutes-From-Boston.h100634230.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)

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

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/1182d313.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)

### Vacation Home in East Somerville

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

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 $109

CA $487 total

includes taxes & fees

Feb 25 - Feb 26

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

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/575dabbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/5f5eeead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/be7451ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/f53a1c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

[](https://www.expedia.ca/Boston-Hotels-Charming-3-Beds-In-2-Bedrooms-Apartment-Near-Quincy-Adams.h119138331.Hotel-Information)

10/10

Exceptional

(1 review)

"Nice amount of room and overall cleanliness."

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

Jodi A.

CA $226

CA $393 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Boston-Hotels-Charming-3-Beds-In-2-Bedrooms-Apartment-Near-Quincy-Adams.h119138331.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/120000000/119350000/119344500/119344472/902d4a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119350000/119344500/119344472/58cdebce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119350000/119344500/119344472/d19ef814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119350000/119344500/119344472/24ff865e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Randolph

[](https://www.expedia.ca/Boston-Hotels-17-4BR-Randolph-Cozy-House.h119344472.Hotel-Information)

10/10

Exceptional

(4 reviews)

"It was a cozy and clean home with everything needed to accommodate your stay. My family and young nephews had a great time here and I’d recommend it to anyone looking to visit Boston"

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

Nicholas P.

CA $225

CA $529 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Boston-Hotels-17-4BR-Randolph-Cozy-House.h119344472.Hotel-Information)

![](https://images.trvl-media.com/lodging/96000000/95810000/95804200/95804146/24643daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/96000000/95810000/95804200/95804146/ed4ad96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/96000000/95810000/95804200/95804146/4b3498c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/96000000/95810000/95804200/95804146/abe708f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Billerica

[](https://www.expedia.ca/Billerica-Hotels-Lake-Access-4-Bed-3-Full-Bath.h95804146.Hotel-Information)

9.8/10

Exceptional

(22 reviews)

"The house was perfect for us! Sparkling clean and comfortable. We really enjoyed staying here and would stay again for sure!"

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

Diane B.

CA $366

CA $966 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Billerica-Hotels-Lake-Access-4-Bed-3-Full-Bath.h95804146.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101301600/101301592/29251454.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/102000000/101310000/101301600/101301592/5790b9f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/102000000/101310000/101301600/101301592/b78fddd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/102000000/101310000/101301600/101301592/891ebba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Marblehead

[](https://www.expedia.ca/Boston-Hotels-The-Widows-Walk-Your-Very-Own-Spa-Experience.h101301592.Hotel-Information)

9.4/10

Exceptional

(20 reviews)

"Great location with incredible views! House is great, lots of amenities - family loved it and already wants to go back!"

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

Jonathan T.

CA $451

CA $869 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Boston-Hotels-The-Widows-Walk-Your-Very-Own-Spa-Experience.h101301592.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92050000/92049600/92049583/w1024h489x0y97-43640a8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dorchester

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

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 $245

CA $617 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Boston-Hotels-Centrally-Located-In-The-Heart-Of-Boston-Near-T.h92049583.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=2026-03-10&endDate=2026-03-11&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_175481)

## 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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APART_HOTEL)

Apartments

[](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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT)

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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO)

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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA)

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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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

"Staff went above and betond. Room was exceptional "

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

![DoubleTree Suites by Hilton Hotel Boston - Cambridge](https://images.trvl-media.com/lodging/1000000/10000/1000/946/e477f850_y.jpg)

### DoubleTree Suites by Hilton Hotel Boston - Cambridge

10/10 Excellent

"The staff was amazing..... every single person. The room was very clean and comfortable. The only complaint I would have is that the restaurant could use more offerings and was very pricey. But again, the service was great so I still went with 5 stars!"

[](https://expedia.ca/Boston-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Boston-Cambridge.h946.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

"The staff was extremely professional and very helpful"

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

"Clean and perfect for a weekend getaway easy check in and check out nice staff and nice lounge "

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

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

### The Dagny Boston

10/10 Excellent

"The room was spotless and they did a great job each day there. Also parking valet was awesome along with door staff "

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

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

### Hilton Boston Logan Airport

10/10 Excellent

"Clean"

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

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

### Omni Boston Hotel at the Seaport

10/10 Excellent

"The rooms were very clean and the staff was very helpful with everything we needed "

[](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

"Excellent stay. Hotel is beautiful and staff are friendly and helpful. Would definitely return. "

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

![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg)

### Hilton Boston Park Plaza

10/10 Excellent

"Richard at the Front Desk was wonderful. He started opur experiences with a woinderful greeting and then upgraded our room because it was my husbands birthday. Then gave him a $50 gift voucher as a birthday gift to spend at the hotel! Now, that's taking care of your clients. Thanks Richard!"

[](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information)

## Find out more about Winchester

## Winchester Vacation Homes information

| Number of reviews | 334                |
| ----------------- | ------------------ |
| Accommodation     | 544 Vacation Homes |
| Lowest Price      | CA $362            |
| Highest Price     | CA $966            |

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