Title: Winchester Condo Rentals from CA $297 | Expedia.ca

  

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# Search Condos Rentals in Winchester from CA $297

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## Check prices for these dates

Next weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Winchester Condo Rentals

![Marina](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/127156b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/ba0817f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/9dd306c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/44314df0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

Marblehead

10/10

Exceptional

(67)

"I was beyond impressed with my stay here in Marblehead! As a solo traveler, I felt safe in this Vrbo property. Everything was beyond clean, access was easy, and having a dedicated parking spot was amazing. It was the perfect place to stay!"

CA $204

CA $450 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Boston-Hotels-Historic-StudioMinutes-To-SalemBeachesOld-Town-MarbleheadPrivate-Parking.h78763861.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/65000000/64470000/64465500/64465407/e6f5f4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/65000000/64470000/64465500/64465407/fd032dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64470000/64465500/64465407/a27fa3a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64470000/64465500/64465407/7a860e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Suite at House of L: near Boston, Hospitals, Encore Casino, Walk to Bus, Fast WiFi, Driveway

Chelsea

9.0/10

Wonderful

(30)

"Good location with a quick drive to downtown areas, property felt safe and secure, comfortable bedding, good for a weekend trip to Boston! Well stocked with supplies, I appreciated having the off street parking spot, I enjoyed the small space with seating area outside. The tenants upstairs were not loud overnight which was much appreciated. "

CA $169

CA $520 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Boston-Hotels-All-Newly-Renovated-Private-Apartment-Near-Encore-Casino.h64465407.Hotel-Information)

![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/119000000/118250000/118246100/118246040/36a4287f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118250000/118246100/118246040/8b697cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118250000/118246100/118246040/8b0120f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/119000000/118250000/118246100/118246040/616f2774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern & Stylish 1-Bedroom Condo near Downtown

Roxbury

10/10

Exceptional

(4)

"Very nice and quiet neighborhood. Would love to rent again if the opportunity presents itself. "

CA $187

CA $522 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Boston-Hotels-Modern-Stylish-1-Bedroom-Condo-Near-Downtown.h118246040.Hotel-Information)

![On the beach, fishing](https://images.trvl-media.com/lodging/110000000/109120000/109115300/109115211/51b527db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109120000/109115300/109115211/26daa613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109120000/109115300/109115211/066801e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/110000000/109120000/109115300/109115211/837a8edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Village Retreat: Walk to Charming Historic Town, Off Street Parking, Private Deck, Grill

Marblehead

CA $441

CA $899 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Boston-Hotels-Village-Retreat-Private-Deck.h109115211.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/e53a97d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/6e3991e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/fde4bc74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/314b2ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lg suite for up to 8 ppl/2 floor

Dorchester

10/10

Exceptional

(12)

"The apartment was perfect, just as advertised. Very clean and comfortable. Would not hesitate to stay there again."

CA $216

CA $688 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl2-Floor.h21318003.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/f49166bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/e39f6a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/cedb4307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/e5ab999a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Framingham

10/10

Exceptional

(2)

"Very nice and private. Reasonably close to commuter lines into Boston."

CA $181

CA $297 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Boston-Hotels-Private-Cozy-1-Br-Condo-W-High-Ceilings.h114549922.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/786d5023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/7ede498b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/da5ecf61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/a13661ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal Charm: Lobster Châto

Swampscott

8.0/10

Very good

(3)

"Beautiful house & views,"

CA $609

CA $1,289 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Boston-Hotels-Coastal-Charm-Lobster-Chato.h107986920.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/8fcb923c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/96909653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/8ef354bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/15d25d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish home next to train to Boston, near Salem

Wakefield

10/10

Exceptional

(3)

"we were in Massachusetts for our youngest granddaughters college graduation. This place was great. Good location and great hosts! Beautiful neighborhood Easy to walk to breakfast, lunch or dinner. "

CA $230

CA $603 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Stylish-Home-Next-To-Train-To-Boston.h106882526.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/21000000/20110000/20104300/20104203/56aa4e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/21000000/20110000/20104300/20104203/07fd84db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo](https://images.trvl-media.com/lodging/21000000/20110000/20104300/20104203/9a47d441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20110000/20104300/20104203/01c70e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Great South End / Back Bay location, 1 bed condo near T station

South End

10/10

Exceptional

(96)

"The location was outstanding offering easy access to all attractions and public transportation, all while being situated on a quiet street. The host was the best I've ever encountered-extremely responsive and attentive to all our needs. I was concerned about parking since we drove in, but the garage was only 2 blocks away and secure. Dropping off luggage first at the house was no problem. Would stay here again and recommend."

CA $488

CA $733 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Boston-Hotels-Great-South-End-Back-Bay-Location.h20104203.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/507e379a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/fd3fe208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/532179dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/2be55ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Three Bedroom Condo - Near Boston

stoneham

8.8/10

Excellent

(8)

"Two friends and myself went to Boston for a concert and stayed in this house. The description was right on and the house fit our needs. I would rent this property again if i go back to Boston. "

CA $308

CA $699 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Boston-Hotels-Modern-Three-Bedroom-Condo-Near-Boston.h78069315.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112640000/112637400/112637397/19521cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112640000/112637400/112637397/2a578fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/113000000/112640000/112637400/112637397/b1c103c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112640000/112637400/112637397/26d15105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your cozy home away from home, close to subway and downtown Boston

Jamaica Plain

9.0/10

Wonderful

(8)

"Great place ideally located."

CA $244

CA $597 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Boston-Hotels-Your-Cozy-Home-Away-From-Home.h112637397.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/f14f14bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/7e4f8d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/3525cfe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/1d3faad4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Everett

10/10

Exceptional

(27)

"Excellent place for our stay during my daughter's graduation at Tufts. "

CA $297

CA $663 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Boston-Hotels-Large-Modern-Luxury-Duplex-Home-Close-To-Boston-Cambridge-With-Free-Parking.h35353788.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/da8ea1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/8d805301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/fa8ae97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/5106b1bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 🎖The Ashmont Suite - Close to Subway + Downtown🎖

Dorchester

10/10

Exceptional

(53)

"The historic Victorian home is amazing! So much space and has everything you would need for a great stay. "

CA $347

CA $676 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Boston-Hotels-The-Ashmont-Suite-Close-To-Subway-Downtown.h78813350.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/68d357d3.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/40000000/39540000/39536400/39536322/e10b81af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/26112e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/c04cfe85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright & Spacious Loft Steps to the Freedom Trail

Downtown Boston

10/10

Exceptional

(48)

"Great apartment and well stocked kitchen close to Boston's freedom trail and best sites."

CA $627

CA $1,025 total

includes taxes & fees

Oct 24 - Oct 25

[](https://www.expedia.ca/Boston-Hotels-Bright-Spacious-Loft-Steps-To-The-Freedom-Trail.h39536322.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78480000/78474400/78474311/d92bd62c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78480000/78474400/78474311/21f26d99.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/79000000/78480000/78474400/78474311/8c668f61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78480000/78474400/78474311/21832882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely Two Bedroom Condo in South Boston

South Boston

7.8/10

Good

(6)

"Very clean "

CA $350

CA $793 total

includes taxes & fees

Oct 20 - Oct 21

[](https://www.expedia.ca/Boston-Hotels-Lovely-Two-Bedroom-Condo-In-South-Boston.h78474311.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/113000000/112080000/112077700/112077628/a636ddb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/113000000/112080000/112077700/112077628/248ca26b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112080000/112077700/112077628/a98c2248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/113000000/112080000/112077700/112077628/w1114h738x0y0-74fb2d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning Waterfront Condo with Boston Skyline Views

East Boston

10/10

Exceptional

(5)

"The condo is exactly as listed: spacious, comfortable, beautiful. The outdoor space is fantastic. Love the neighborhood: can walk to the waterfront park which is lovely; view of Boston over the harbor, and access Boston proper very easily. The hosts and manager are amazing at communicating and responded promptly to all questions. This is a very perfect rental. "

CA $484

CA $1,277 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Boston-Hotels-Stunning-Waterfront-Condo-With-Boston-Skyline-Views.h112077628.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/c03cf901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/fe833037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games, books](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/83277e2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/8552e368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Back-Bay Upscale Central Condo Bos Common Downtown

Bay Village

10/10

Exceptional

(7)

"Great location for this apartment. Check in was a breeze. Would definitely come back and stay here!"

CA $658

CA $1,590 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Boston-Hotels-Back-Bay-Upscale-Central-Condo-Bos-Common-Downtown.h109549335.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104530000/104521000/104520937/379fe9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104530000/104521000/104520937/afe117a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104530000/104521000/104520937/6ead8796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104530000/104521000/104520937/f74ad51d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Large victorian home 15 mins from downtown lots of local restaurants and bars

Mattapan

8.6/10

Excellent

(4)

"Host was quick to respond and helpful. It had very spacious living area. There is a king bed, all the "queen" beds were actually doubles. There were bath towels but no washcloths. There was a Keurig, not coffee maker as advertised. It was sufficient for our two day stay. We had a great visit to Boston. The house location was easy driving to the harbor walk and seaport district. We were able to Uber relatively cheap to Fenway and downtown Boston. It was overall a good experience with this host. ...

CA $816

CA $1,713 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Boston-Hotels-Victorian-Home.h104520937.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21320000/21318000/21317934/4ae52d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21320000/21318000/21317934/78b4a0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21320000/21318000/21317934/18097d81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/22000000/21320000/21318000/21317934/291671d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lg Suite for up to 8 ppl/1 floor

Dorchester

9.0/10

Wonderful

(14)

"Great place! Plenty of room, clean, and well kept. Very close to a ton of stuff to see and do. Highly recommend!"

CA $202

CA $669 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl1-Floor.h21317934.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Top Winchester Hotel Reviews

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

### citizenM Boston North Station

10/10 Excellent

"safe"

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

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

### The Dagny Boston

10/10 Excellent

"Clean room and staff were awesome."

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

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

### Harborside Inn Of Boston

10/10 Excellent

"Had a great day here. Recommended"

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

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

### The Langham, Boston

10/10 Excellent

"Hotel was great. Large room and bathroom and great facilities at the hotel. Front desk services were very helpful On arrival. Close to lots of things and the city is very walkable. Loved our stay."

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

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

### YOTEL Boston

10/10 Excellent

"Great place to stay. Do not stay if you need space—these rooms are tiny. However, it's great for a couple's getaway if you are okay with limited privacy, particularly in the bathroom. Perfect location. You can walk to everything. Literally everything. Very Clean property. "

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

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

### The Revolution Hotel

10/10 Excellent

"Room was very clean. We had a bathroom in the room and a small cooking/eating area. We were really impressed and would gladly stay again. Beds very comfortable. "

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

![Copley Square Hotel, a FOUND Hotel](//images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb_y.jpg)

### Copley Square Hotel, a FOUND Hotel

10/10 Excellent

"Historic hotel, great location the rooms are small but very practical!"

[](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information)

![Sheraton Boston, a Marriott Hotel](//images.trvl-media.com/lodging/1000000/30000/22100/22046/dfa592c9_y.jpg)

### Sheraton Boston, a Marriott Hotel

10/10 Excellent

"Staff was very professional and very helpful. Hotel is really nice and updated."

[](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information)

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

### Encore Boston Harbor

10/10 Excellent

"SIMPLY AMAZING. This is the best hotel I ever stayed at so far. Definitely the best one in Boston and perhaps the state of Massachusetts. 10/10 all around."

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

## Find out more about Winchester

## Winchester Condo Rentals information

| Number of reviews | 378 |
| --- | --- |
| Accommodation | 183 Condo Rentals |
| Lowest Price | CA $297 |
| Highest Price | CA $1,713 |

## Frequently asked questions

### How much do condos in Winchester cost?

> Condos in Winchester range from CA $297 to CA $1,713 per night. These properties offer loads of space for the whole family at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

### How many condos are there in Winchester?

> Take your pick of 183 condos in Winchester. No matter if you're traveling with the kids or planning a weekend escape with your buddies, Expedia will help you find the right space for your entire crew.

### Why book your condo in Winchester with Expedia?

> Booking a condo in Winchester is as simple as deciding on your travel dates and selecting an option that satisfies your needs. Seeking something upscale or budget friendly, or a stay that also features a laundry and kitchen? Use Expedia's search filters to further narrow your search results and find the ideal fit at the right price.

### How can I find cheap condos in Winchester?

> A great way to locate cheap condos in Winchester is with Expedia's handy filter tool. Refine your search by star rating, amenities and budget to access awesome rates in a few clicks.

### What is there to do in Winchester near my condo?

> The most useful travel accessory is a well-planned itinerary. [Winter Pond](https://www.expedia.ca/Winter-Pond-Boston.d553248621561930456.Vacation-Attraction) is a terrific place to kick-start your adventures in Winchester.

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