Title: Winchester Condo Rentals from CA $293 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/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) # Search Condos Rentals in Winchester from CA $293 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three 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 four 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) ## Our top choices for Winchester condo rentals ![Exterior detail](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/58691629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/89de23c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/a0975d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/dcd26c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Beacon Hill [](https://www.expedia.ca/Boston-Hotels-Charming-Private-1-Bedroom-Condo-In-Historic-Boston-Next-To-MGH-Hospital.h122591889.Hotel-Information) CA $132 CA $373 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Boston-Hotels-Charming-Private-1-Bedroom-Condo-In-Historic-Boston-Next-To-MGH-Hospital.h122591889.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/127156b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/151e1632.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/a0dfcd08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/a9ded59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Marblehead [](https://www.expedia.ca/Boston-Hotels-Historic-StudioMinutes-To-SalemBeachesOld-Town-MarbleheadPrivate-Parking.h78763861.Hotel-Information) 10/10 Exceptional (70) "The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela O. CA $90 CA $303 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Historic-StudioMinutes-To-SalemBeachesOld-Town-MarbleheadPrivate-Parking.h78763861.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/bae9ad93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/ea1de69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/82393db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/29adffae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Marblehead [](https://www.expedia.ca/Boston-Hotels-Charming-1-Bedroom-Condo-In-Marvelous-Marblehead-With-Hidden-Patio.h121274557.Hotel-Information) 10/10 Exceptional (2) "This place is awesome. First time going to the east and I’d rather stay here over any 5 star hotel. Janie is so nice n gave some great suggestions for bars/places to eat while there. The only bad part about the trip was having to go home. Easy parking, fairy tale like back yard area, historic house, and only a 4 minute walk to the ocean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madison J. CA $116 CA $237 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Boston-Hotels-Charming-1-Bedroom-Condo-In-Marvelous-Marblehead-With-Hidden-Patio.h121274557.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/973ca28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/5712aadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/a17d20b9.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/69000000/68770000/68769100/68769097/ee99841d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Beverly [](https://www.expedia.ca/Boston-Hotels-NEW-Spacious-2BrDowntownBeverlySalemParking.h68769097.Hotel-Information) 10/10 Exceptional (32) "The home was nicely renovated and comfortable and our hosts were quick to respond to questions. Check in and out was easy and we had a nice stay and will return. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence D. CA $143 CA $403 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-NEW-Spacious-2BrDowntownBeverlySalemParking.h68769097.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/5ffeb434.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/0aaf004a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/7125f8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/275d54b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Salem [](https://www.expedia.ca/Salem-Hotels-Downtown-Salem-Park-Play-Modern-3-Bedroom.h72612302.Hotel-Information) 10/10 Exceptional (58) "This was a truly wonderful property - clean, generously stocked, perfect location and attentive owner" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie G. CA $180 CA $489 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Salem-Hotels-Downtown-Salem-Park-Play-Modern-3-Bedroom.h72612302.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w903h683x60y0-08da216e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w906h683x60y0-b8c24bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w904h683x60y0-cc071546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w505h683x260y0-fe4c31f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Ward Two [](https://www.expedia.ca/Boston-Hotels-Boston-2bd-King-Bed-Near-Harvard.h95470643.Hotel-Information) 9.8/10 Exceptional (19) "Excellent place to stay! Close to the T Red line, shopping and food. Quiet accommodations with good Wi-Fi. Nice neighborhood for exploring." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric D. CA $182 CA $453 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Boston-Hotels-Boston-2bd-King-Bed-Near-Harvard.h95470643.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/4aa77cbd.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/97000000/96890000/96884400/96884357/f076b1e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/510df553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/f3ab5f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Salem [](https://www.expedia.ca/Boston-Hotels-Historic17102Br-7PplHalloweenSalemFreeParking.h96884357.Hotel-Information) 10/10 Exceptional (59) "We had a fantastic time here! The home was so charming and comfortable, and we loved the decor. The location couldn’t be more perfect (we were able to walk to all the sights we wanted to see in Salem), and the hosts are also very communicative. It truly exceeded our expectations. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin B. CA $238 CA $518 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Historic17102Br-7PplHalloweenSalemFreeParking.h96884357.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/da52403c.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) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/dffc6e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/94040174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Swampscott [](https://www.expedia.ca/Boston-Hotels-Coastal-Charm-Lobster-Chato.h107986920.Hotel-Information) 8.4/10 Very good (6) "My husband and i loved the ocean front views and sounds and walk on the beach in the morning The location was great close to salem and marblehead a beautiful little town . The place was clean and we loved the eclectic antique style and furnishings that were super comfortable also love the big wood burning fireplace..our Host was top notch immediate response and care for whatever you needed made for a great experience. Also briefly met the owner such a really nice person . We will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen M. CA $300 CA $844 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Coastal-Charm-Lobster-Chato.h107986920.Hotel-Information) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/1c623532.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) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/242b01a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Framingham [](https://www.expedia.ca/Boston-Hotels-Private-Cozy-1-Br-Condo-W-High-Ceilings.h114549922.Hotel-Information) 10/10 Exceptional (4) "Very nice and private. Reasonably close to commuter lines into Boston." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenny S. CA $179 CA $293 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Boston-Hotels-Private-Cozy-1-Br-Condo-W-High-Ceilings.h114549922.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/68ef654d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/6cc5c42e.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/fef75b82.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) ### Condo in Wakefield [](https://www.expedia.ca/Stylish-Home-Next-To-Train-To-Boston.h106882526.Hotel-Information) 10/10 Exceptional (5) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca Z. CA $204 CA $562 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Stylish-Home-Next-To-Train-To-Boston.h106882526.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118250000/118246100/118246040/5a226ad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/119000000/118250000/118246100/118246040/839a96d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, iron/ironing board](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/119000000/118250000/118246100/118246040/8b0120f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roxbury [](https://www.expedia.ca/Boston-Hotels-Modern-Stylish-1-Bedroom-Condo-Near-Downtown.h118246040.Hotel-Information) 10/10 Exceptional (5) "Very clean home with modern updates. Easy check-in. Hosts are very communicative and care that you are good to go while staying in their home. We came in town for the Red Sox game and the home is within a short Uber ride to Fenway. 10 out of 10 recommend you stay at this home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen L. CA $231 CA $568 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Modern-Stylish-1-Bedroom-Condo-Near-Downtown.h118246040.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108580000/108577000/108576990/e2d94571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108580000/108577000/108576990/32a87f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108580000/108577000/108576990/0527601c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108580000/108577000/108576990/e2b0f61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Salem [](https://www.expedia.ca/Boston-Hotels-Charming-3-Bedroom-Condo-With-AC-And-WiFi-In-Welcoming-Salem.h108576990.Hotel-Information) 10/10 Exceptional (6) "4 adults and one toddler stayed at unit . Very clean and up to date . Great location to Boston and North Shore . Walking distance to nice park and coffee houses. Enjoyed our stay !! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff C. CA $186 CA $413 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boston-Hotels-Charming-3-Bedroom-Condo-With-AC-And-WiFi-In-Welcoming-Salem.h108576990.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121790000/121789000/121788903/8b574a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121790000/121789000/121788903/f16d3388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/122000000/121790000/121789000/121788903/0c185fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/122000000/121790000/121789000/121788903/c017b58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Beverly [](https://www.expedia.ca/Boston-Hotels-Modern-2-Bedroom-Condo-1-Mile-To-Salem.h121788903.Hotel-Information) 10/10 Exceptional (1) "We had a wonderful stay!! Excellent location with many walking distance food options. Super clean and super cozy!! Hosts were responsive and caring for our comfort while we stayed. Thank you for the snacks!!! We would definitely stay here again!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa G. CA $378 CA $545 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Modern-2-Bedroom-Condo-1-Mile-To-Salem.h121788903.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) ![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) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/7347d3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Dorchester [](https://www.expedia.ca/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl2-Floor.h21318003.Hotel-Information) 10/10 Exceptional (12) "It was a perfect location for our daily plans. The owner was very responsive to our needs " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary P. CA $193 CA $643 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl2-Floor.h21318003.Hotel-Information) ![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/116000000/115820000/115817400/115817302/ed95f9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115820000/115817400/115817302/w405h182x0y359-6e3226e1.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/116000000/115820000/115817400/115817302/a6fed9c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/116000000/115820000/115817400/115817302/48e8ab5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Chelsea [](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Condo-In-Delightful-Chelsea-With-WiFi.h115817302.Hotel-Information) 10/10 Exceptional (1) "Very happy with our stay here! The place was clean, warm, and comfortable. I really appreciated the easy check in/out procedures. I loved that we weren’t expected to complete a long list of cleaning tasks before checking out. Crib, pack n play, and high chair were available which is awesome for traveling with a baby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amna S. CA $260 CA $587 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Condo-In-Delightful-Chelsea-With-WiFi.h115817302.Hotel-Information) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/f342fda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/3c055933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/af1458e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/5a7cb474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Everett [](https://www.expedia.ca/Boston-Hotels-Large-Modern-Luxury-Duplex-Home-Close-To-Boston-Cambridge-With-Free-Parking.h35353788.Hotel-Information) 10/10 Exceptional (30) "Great location! Host was very attentive. Enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim H. CA $251 CA $592 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Large-Modern-Luxury-Duplex-Home-Close-To-Boston-Cambridge-With-Free-Parking.h35353788.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83470000/83465000/83464949/55f2c812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83470000/83465000/83464949/f190b94c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83470000/83465000/83464949/1ccdb547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/84000000/83470000/83465000/83464949/a6bb145f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Salem [](https://www.expedia.ca/Boston-Hotels-The-Warlock-House-Speak-Spells.h83464949.Hotel-Information) 9.6/10 Exceptional (61) "Amazing place to stay! Love the attention to decorating details, from the spooky lighting to the Alexa “Scroll of Spells” and it’s within close walking distance to many Salem attractions! Would recommend to anyone!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) More M. CA $428 CA $1,010 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-The-Warlock-House-Speak-Spells.h83464949.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/2de70c1e.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/d13907a0.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) ![Interior](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/ef31c618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in stoneham [](https://www.expedia.ca/Boston-Hotels-Modern-Three-Bedroom-Condo-Near-Boston.h78069315.Hotel-Information) 9.0/10 Wonderful (9) "We enjoyed our stay and would definitely stay here again. It was clean, cute, very cute area, safe, and very short drive to Boston. We really loved the area and the people we interacted with were all so friendly! The beds were very comfy too!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meghan D. CA $338 CA $732 total includes taxes & fees Dec 23 - Dec 24 [](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/123000000/122120000/122110400/122110307/6d195cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/6d0631d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/ce13f62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/7b35e7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in East Boston [](https://www.expedia.ca/Boston-Hotels-Eastie-Gem-Taste-Of-Local-Life-By-The-Waterfront.h122110307.Hotel-Information) CA $278 CA $597 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Boston-Hotels-Eastie-Gem-Taste-Of-Local-Life-By-The-Waterfront.h122110307.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101210000/101209300/101209282/94c0c1eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101210000/101209300/101209282/c751d289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/102000000/101210000/101209300/101209282/ccd45172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, offices](https://images.trvl-media.com/lodging/102000000/101210000/101209300/101209282/15e89230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Beverly [](https://www.expedia.ca/Boston-Hotels-New-Spacious5Br-Sleeps10Halloween-SalemBeverly.h101209282.Hotel-Information) CA $367 CA $970 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-New-Spacious5Br-Sleeps10Halloween-SalemBeverly.h101209282.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=2025-12-31&endDate=2026-01-01®ionId=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®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=COTTAGE) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Condos.d175481-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Condos.d175481-aaCondos.Travel-Guide-Accommodation) ## 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 "We had a nice stay at this place, check in is a breeze, everyone is very nice. The bed is comfy, the room is nice and clean. The location is really good too, Macy’s is across the street, walking distance to Boston common and Faneuil Hall Market place, and North end. We will difinitely stay here again. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Clean room and helpful staff. A lot of restaurant and pub n’est the Hotel. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "Class hotel with amazing history " [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![The Arcadian Hotel](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 10/10 Excellent "Very clean and the staff was friendly. Parking is a little tricky but that's to be expected. Would definitely go back. " [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.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 "Beautiful view! Clean. Convenient location " [](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 "Good" [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "Excellent spa" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg) ### Hilton Boston Back Bay 10/10 Excellent "The hotel is undergoing renovations which will be an exciting improvement. Still a great staff and excellent location. Will return! " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 10/10 Excellent "Yes" [](https://expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ## Find out more about Winchester ## Winchester Condo Rentals information | Number of reviews | 346 | | ----------------- | ----------------- | | Accommodation | 172 Condo Rentals | | Lowest Price | CA $293 | | Highest Price | CA $1,010 | ## Frequently asked questions ### How much do condos in Winchester cost? ### How many condos are there in Winchester? ### Why book your condo in Winchester with Expedia? ### How can I find cheap condos in Winchester? ### What is there to do in Winchester near my condo? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Aparthotels in Arlington ](https://www.expedia.ca/Arlington-Apart-Hotels.d74693-aaApartHotels.Travel-Guide-Accommodation) - 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