Title: Winchester, MA Condos for Rent | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx175481)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/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) ![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/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 three months [Jun 19 - Jun 21](https://www.expedia.com/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) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-07-17&endDate=2026-07-19&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) ![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) ![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) ### Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital! [](https://www.expedia.com/Boston-Hotels-Charming-Private-1-Bedroom-Condo-In-Historic-Boston-Next-To-MGH-Hospital.h122591889.Hotel-Information) Beacon Hill 9.6/10 Exceptional (4 reviews) "It was a great place. Good location, clean, comforable and the host was quick with a few questions that we had. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather A. $250 nightly $287 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Charming-Private-1-Bedroom-Condo-In-Historic-Boston-Next-To-MGH-Hospital.h122591889.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/1620a08b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/590d6596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/807928be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/470d7dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coastal Charm: Lobster Châto [](https://www.expedia.com/Boston-Hotels-Coastal-Charm-Lobster-Chato.h107986920.Hotel-Information) Swampscott 8.4/10 Very Good (6 reviews) "The view is amazing! Great communication with the host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bonnie V. $523 nightly $557 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Coastal-Charm-Lobster-Chato.h107986920.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/f2bcef31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/9d309006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/d0bd9452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/a95b3766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Three Bedroom Condo - Near Boston [](https://www.expedia.com/Boston-Hotels-Modern-Three-Bedroom-Condo-Near-Boston.h78069315.Hotel-Information) stoneham 9.0/10 Wonderful (10 reviews) "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. $468 nightly $494 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Modern-Three-Bedroom-Condo-Near-Boston.h78069315.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) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/60cad7f7.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) ![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 [](https://www.expedia.com/Stylish-Home-Next-To-Train-To-Boston.h106882526.Hotel-Information) Wakefield 9.4/10 Exceptional (6 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex c. $337 nightly $376 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Stylish-Home-Next-To-Train-To-Boston.h106882526.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/806f68c7.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/40000000/39540000/39536400/39536322/957fbf4b.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 [](https://www.expedia.com/Boston-Hotels-Bright-Spacious-Loft-Steps-To-The-Freedom-Trail.h39536322.Hotel-Information) Downtown Boston 10/10 Exceptional (53 reviews) "Trendy, clean room in great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel M. $292 nightly $335 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Bright-Spacious-Loft-Steps-To-The-Freedom-Trail.h39536322.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/1c623532.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 [](https://www.expedia.com/Boston-Hotels-Private-Cozy-1-Br-Condo-W-High-Ceilings.h114549922.Hotel-Information) Framingham 10/10 Exceptional (4 reviews) "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. $192 nightly $214 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Private-Cozy-1-Br-Condo-W-High-Ceilings.h114549922.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) ![Exterior](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/c73fcc45.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) ![1 bedroom, 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) ### ♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥ [](https://www.expedia.com/Boston-Hotels-Historic-Studio-Minutes-To-SalemBeaches-Old-Town-Marblehead-Private-Parking.h78763861.Hotel-Information) Marblehead Historic District 10/10 Exceptional (72 reviews) "Super convenient location; quaint old building; spacious apartment with comfortable bed, seating, and well appointed kitchen and bath. Easy checkin, checkout, and access. Thanks for a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara D. $225 nightly $251 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Historic-Studio-Minutes-To-SalemBeaches-Old-Town-Marblehead-Private-Parking.h78763861.Hotel-Information) ![TV, video games](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/24c04e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/373c48fa.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/ece832ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109550000/109549400/109549335/57a58639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Back-Bay Upscale Central Condo Bos Common Downtown [](https://www.expedia.com/Boston-Hotels-Back-Bay-Upscale-Central-Condo-Bos-Common-Downtown.h109549335.Hotel-Information) Bay Village 10/10 Exceptional (10 reviews) "Everything went smoothly with booking, checking in and checking out. Unit was as nice as the description and photos." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen C. $739 nightly $848 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Back-Bay-Upscale-Central-Condo-Bos-Common-Downtown.h109549335.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96740000/96735900/96735817/w903h683x60y0-60fc025a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96740000/96735900/96735817/w903h683x60y0-1aa8d117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96740000/96735900/96735817/w905h683x59y0-6cc5962f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96740000/96735900/96735817/w904h683x60y0-10173540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Salem Chic - 3 Bedroom w/ Parking [](https://www.expedia.com/Boston-Hotels-Downtown-Salem-Chic.h96735817.Hotel-Information) Salem 10/10 Exceptional (5 reviews) "Check in went very smooth and kitchen was well stocked with everything needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Justin R. $337 nightly $376 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Downtown-Salem-Chic.h96735817.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/105000000/104950000/104940600/104940575/da352403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104950000/104940600/104940575/be0aeaec.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/105000000/104950000/104940600/104940575/6ed7be25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104950000/104940600/104940575/87c3cc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern, Spacious Condo, minutes to downtown Salem, Private Parking on Site! [](https://www.expedia.com/Boston-Hotels-Modern.h104940575.Hotel-Information) Salem 10/10 Exceptional (12 reviews) "Such a wonderful spot, super clean and spacious within walking distance of downtown Salem! The beds were so comfortable and the bathroom was fully stocked. We loved our stay and appreciated the ease of check-in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mallory M. $486 nightly $543 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Modern.h104940575.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) ![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) ![Interior](https://images.trvl-media.com/lodging/116000000/115820000/115817400/115817302/ae086a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom condo in delightful Chelsea with WiFi, AC [](https://www.expedia.com/Boston-Hotels-Charming-2-Bedroom-Condo-In-Delightful-Chelsea-With-WiFi.h115817302.Hotel-Information) Chelsea 10/10 Exceptional (2 reviews) "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. $397 nightly $443 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Charming-2-Bedroom-Condo-In-Delightful-Chelsea-With-WiFi.h115817302.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) ![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/b790839c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Salem - Park & Play Modern 3 Bedroom [](https://www.expedia.com/Salem-Hotels-Downtown-Salem-Park-Play-Modern-3-Bedroom.h72612302.Hotel-Information) Salem 10/10 Exceptional (63 reviews) "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. $351 nightly $392 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Salem-Hotels-Downtown-Salem-Park-Play-Modern-3-Bedroom.h72612302.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/599769d4.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) ![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/007ceb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lg suite for up to 8 ppl/2 floor [](https://www.expedia.com/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl2-Floor.h21318003.Hotel-Information) Dorchester 10/10 Exceptional (12 reviews) "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. $387 nightly $445 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl2-Floor.h21318003.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) ![TV](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/90be1e7c.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) ### Charming 1-bedroom condo in marvelous Marblehead with hidden patio [](https://www.expedia.com/Boston-Hotels-Charming-1-Bedroom-Condo-In-Marvelous-Marblehead-With-Hidden-Patio.h121274557.Hotel-Information) Marblehead Historic District 10/10 Exceptional (3 reviews) "Darling apartment - perfectly located close to shops and restaurants in downtown Marblehead. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren P. $236 nightly $263 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Charming-1-Bedroom-Condo-In-Marvelous-Marblehead-With-Hidden-Patio.h121274557.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/125000000/124470000/124467100/124467075/dc18e02c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124467100/124467075/d5cd0ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124470000/124467100/124467075/6fa67ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124470000/124467100/124467075/53e937f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prestigious Milton Designer Home [](https://www.expedia.com/Boston-Hotels-Prestigious-Milton-Designer-Home.h124467075.Hotel-Information) Milton $364 nightly $385 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Prestigious-Milton-Designer-Home.h124467075.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) ![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) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/a2b17a13.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) ### Eastie Gem: Taste of local life by the waterfront, airport and train [](https://www.expedia.com/Boston-Hotels-Eastie-Gem-Taste-Of-Local-Life-By-The-Waterfront.h122110307.Hotel-Information) East Boston $439 nightly $504 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Eastie-Gem-Taste-Of-Local-Life-By-The-Waterfront.h122110307.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/2a747981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/79000000/78820000/78813400/78813350/31a13689.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) ### 🎖The Ashmont Suite - Close to Subway + Downtown🎖 [](https://www.expedia.com/Boston-Hotels-The-Ashmont-Suite-Close-To-Subway-Downtown.h78813350.Hotel-Information) Dorchester 10/10 Exceptional (55 reviews) "The historic Victorian home is amazing! So much space and has everything you would need for a great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amber M. $449 nightly $516 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Ashmont-Suite-Close-To-Subway-Downtown.h78813350.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104530000/104521000/104520937/1fc7939d.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/de6d5a50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104530000/104521000/104520937/0742f486.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 [](https://www.expedia.com/Boston-Hotels-Large-Victorian-Home-15-Mins-From-Downtown-Lots-Of-Local-Restaurants-And-Bars.h104520937.Hotel-Information) Mattapan 8.4/10 Very Good (7 reviews) "The house was as advertised as far as what was seen in the pictures. Some of the light bulbs/fixtures were not operational, but the house as a whole was very clean and accommodating. Communication with the host was quick and straightforward. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Myles H. $1,136 nightly $1,305 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Large-Victorian-Home-15-Mins-From-Downtown-Lots-Of-Local-Restaurants-And-Bars.h104520937.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.com/Hotel-Search?startDate=2026-04-08&endDate=2026-04-09®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.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APARTMENT) Condos [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VILLA) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=COTTAGE) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Condos.d175481-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Condos.d175481-aaCondos.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Sheraton Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/19346b33_y.jpg) ### Sheraton Boston, a Marriott Hotel 6/10 Okay "Everything about this hotel is fantastic… until you attempt to fall asleep. Check-in was very nice at the front desk. The restaurant and bar were very fancy and had good food/drink options. The room looked nice upon arrival. When attempting to sleep though, it was terrible. There was a service elevator behind my bed, so I head that every time it went up and down. The room was set to 68 for temp, which was nice, but it got so hot in the room at 1:30 that I was sweating and had to take all covers off. The noise in the hallways was so terrible. You could hear every door closing and conversation upon conversation as people walked by. There was an adjoining room next to mine. With that door closed, I could hear the person next to me urinating while standing up. No joke. The bed itself was comfortable, but the pillows were TERRIBLE. Bathroom was nice. Sleep was very limited for 4 nights. Pool and workout area were really nice." [](https://expedia.com/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351_y.jpg) ### citizenM Boston North Station 6/10 Okay "Clean room/areas. Staff was very friendly and kind. Tv did not work in room. " [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Rooms are good, lobby bar is hopping and fun with great bar food. Staff is efficient. BUT remember this hotel is all about its location, in the middle of the airport. Being able to walk to any of the terminals at Logan make this hotel worth the extra expense. HOWEVER I would not have any event at the hotel, it had a very bizzare oder and people walking in front of me, were talking about how it "still" smells. " [](https://expedia.com/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Wonderful place to stay!!" [](https://expedia.com/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hampton Inn Boston - Logan Airport](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/fa1c0549_y.jpg) ### Hampton Inn Boston - Logan Airport 6/10 Okay "u can hear lots of "city noise"all night long" [](https://expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "Wonderful stay! " [](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "We had an interesting situation involving a drunk woman (it was St. Pattys day weekend). The staff was very alert and quick to handle it. Security made us feel more at ease. Only negative I have is that after the incident, we moved rooms, and upon doing so, the woman at front desk never asked for my ID? She just handed me keys. Big no no in the hotel industry. Overall good service, housekeeping did a great job, and the bar area is amazing. Very convenient " [](https://expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "This was a great affordable stay!! It is very small but you get what you’re paying for. The staff was very nice and considerate. There was a random sock in the drawer under the bed so i know housekeeping doesn’t look super through. Also our ipad didn’t work in the room so we couldn’t use some features but I wasn’t in the room enough for that to matter. The decorations in the hotel were so pretty!! Overall a great experience I would stay again." [](https://expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Club Quarters Hotel Faneuil Hall, Boston](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/0c21f6a5_y.jpg) ### Club Quarters Hotel Faneuil Hall, Boston 10/10 Excellent "Quiet and comfortable room in a great location. Room was smaller but cleanliness, service, and value were excellent." [](https://expedia.com/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ## Find out more about Winchester ## Winchester Condo Rentals information | Number of reviews | 298 | | ----------------- | ----------------- | | Accommodation | 172 Condo Rentals | | Lowest Price | $214 | | Highest Price | $1,305 | ## 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 Rentals - Other - [Boston Hotels ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Condo Rentals in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Condos.d6209680-aaCondos.Travel-Guide-Accommodation) - [B&B in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Bed-And-Breakfast.d6209680-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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