Title: Winchester Condo Rentals from CA $298 | 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 $298 - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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 three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Condo Rentals ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/89de23c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/394236e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/58691629.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/fcaab70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Beacon Hill CA $142 CA $390 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) ![Beach](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/43240d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/6d30179e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/bcf24efd.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 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 $145 CA $409 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Boston-Hotels-NEW-Spacious-2BrDowntownBeverlySalemParking.h68769097.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) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/b3e3bd5d.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/fe833037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Bay Village 10/10 Exceptional (10) "Great location for this apartment. Check in was a breeze. Would definitely come back and stay here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean M. CA $278 CA $1,081 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Boston-Hotels-Back-Bay-Upscale-Central-Condo-Bos-Common-Downtown.h109549335.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/c73fcc45.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) ### Condo in Marblehead 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 $104 CA $315 total includes taxes & fees Dec 8 - Dec 9 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/29adffae.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) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/88994b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Marblehead 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 $112 CA $234 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Boston-Hotels-Charming-1-Bedroom-Condo-In-Marvelous-Marblehead-With-Hidden-Patio.h121274557.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) ![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) ![Point of interest](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/8a7b05e1.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) ### Condo in Downtown Boston 10/10 Exceptional (51) "Spacious condo, perfect location, and exceptional hospitality from mangers." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert S. CA $251 CA $525 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-Bright-Spacious-Loft-Steps-To-The-Freedom-Trail.h39536322.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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/15d25d69.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) ### Condo in Wakefield 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 $126 CA $467 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Stylish-Home-Next-To-Train-To-Boston.h106882526.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) ![Dining](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/de66f113.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) ### Condo in stoneham 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 $189 CA $553 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Boston-Hotels-Modern-Three-Bedroom-Condo-Near-Boston.h78069315.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) ![Interior](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/314b2ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/007ceb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Dorchester 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 $210 CA $670 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl2-Floor.h21318003.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118250000/118243900/118243862/e5a99c66.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/119000000/118250000/118243900/118243862/1ab3ce03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/119000000/118250000/118243900/118243862/1db2203b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118250000/118243900/118243862/f1e3d361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Roxbury 10/10 Exceptional (8) "We enjoyed our time in a cozy and very comfortable place. Nice and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henry C. CA $211 CA $546 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Boston-Hotels-Modern-Cozy-3-Bedroom-Condo-Near-Downtown.h118243862.Hotel-Information) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/w1200h799x0y1-3bad3369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/67a15e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/b0259f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/4aa77cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Downtown Salem 10/10 Exceptional (58) "The location of this property in Salem is fantastic, everything and anything is in walking distance." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Ronald CA $242 CA $525 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Boston-Hotels-Historic17102Br-7PplHalloweenSalemFreeParking.h96884357.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) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/116000000/115820000/115817400/115817302/ca46e6b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115820000/115817400/115817302/f4f95b29.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 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 $264 CA $596 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Condo-In-Delightful-Chelsea-With-WiFi.h115817302.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) ![TV](https://images.trvl-media.com/lodging/122000000/121790000/121789000/121788903/d8e753c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121790000/121789000/121788903/0f8aa4f2.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) ### Condo in Beverly 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 $384 CA $554 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Boston-Hotels-Modern-2-Bedroom-Condo-1-Mile-To-Salem.h121788903.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108580000/108577000/108576990/b187fea2.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) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108580000/108577000/108576990/629741a7.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) ### Condo in Salem 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 $212 CA $450 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Boston-Hotels-Charming-3-Bedroom-Condo-With-AC-And-WiFi-In-Welcoming-Salem.h108576990.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w930h683x47y0-9b5726e5.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w508h683x258y0-c36d5519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Ward Two 9.8/10 Exceptional (18) "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 $207 CA $494 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Boston-Hotels-Boston-2bd-King-Bed-Near-Harvard.h95470643.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) ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/5106b1bd.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) ### Condo in Dorchester 10/10 Exceptional (53) "Great house, perfect for our family of 5. Pretty far from Boston and weekend train service was spotty so spent quite a bit on Uber but other than that, a fantastic stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex S. CA $264 CA $578 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Boston-Hotels-The-Ashmont-Suite-Close-To-Subway-Downtown.h78813350.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) ![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) ![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) ### Condo in Swampscott 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 $305 CA $857 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Boston-Hotels-Coastal-Charm-Lobster-Chato.h107986920.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) ![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) ![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) ### Condo in Framingham 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 $182 CA $298 total includes taxes & fees Dec 9 - Dec 10 [](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/36000000/35360000/35353800/35353788/f14f14bc.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) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/93550570.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) ### Condo in Everett 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 $248 CA $597 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Boston-Hotels-Large-Modern-Luxury-Duplex-Home-Close-To-Boston-Cambridge-With-Free-Parking.h35353788.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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/7125f8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/b790839c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Salem 10/10 Exceptional (57) "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 $330 CA $662 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Salem-Hotels-Downtown-Salem-Park-Play-Modern-3-Bedroom.h72612302.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=2025-12-17&endDate=2025-12-18®ionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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 ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Everything and everyone was amazing! 10/10!" [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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 "A+ experience" [](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 "First impression was the friendly,smiling person who checked me in; When I gave her my ID she said,Oh we're birthday twins!!! I really loved the room,and the bed was SO comfortable!! Kohi Coffee in the lobby was amazing as well.Will DEFINITELY be staying there again!!" [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![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 is amazing, very welcoming and friendly. Informative on what is around the area and identifying great restaurants and places to visit. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.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 "Staff was very friendly and helpful. Rooms were clean and new. " [](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 "I loved the breakfast. " [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.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 "Beautiful view, nice room, and lovely hot tub." [](https://expedia.ca/Boston-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Boston-Cambridge.h946.Hotel-Information) ![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg) ### The Westin Copley Place, Boston, a Marriott Hotel 10/10 Excellent "Great location and nice staff " [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information) ![The Newbury Boston](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg) ### The Newbury Boston 10/10 Excellent "Wonderful" [](https://expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ## Find out more about Winchester ## Winchester Condo Rentals information | Number of reviews | 420 | | --- | --- | | Accommodation | 177 Condo Rentals | | Lowest Price | CA $298 | | Highest Price | CA $1,081 | ## Frequently asked questions ### How much do condos in Winchester cost? > Condos in Winchester range from CA $298 to CA $1,081 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 177 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. 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