Title: Winchester, MA Condos for Rent | Expedia.com

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![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-05-29&endDate=2026-05-31&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)

![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)

![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)

### 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

10/10

Exceptional

(2 reviews)

"Had a wonderful stay! Beautiful condo in a beautiful neighborhood that is walking distance to the commons."

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

Grant T.

$238 nightly

$274 total

Feb 10 - Feb 11

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)

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/699992e3.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

(52 reviews)

"Trendy, clean room in great location"

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

Rachel M.

$294 nightly

$337 total

Feb 23 - Feb 24

Total with taxes and fees

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

![Beach](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/d85a1731.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)

![Exterior](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/3a0bd13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884357/24b296aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*New 1710 Historic 2BR |Downtown+Salem|Hocus Pocus

[](https://www.expedia.com/Boston-Hotels-Historic17102Br-7PplHalloweenSalemFreeParking.h96884357.Hotel-Information)

Downtown Salem

10/10

Exceptional

(65 reviews)

"Great location, walking distance to anywhere we wanted to go. Would not hesitate to stay again! "

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

Pat M.

$273 nightly

$312 total

Feb 11 - Feb 12

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Historic17102Br-7PplHalloweenSalemFreeParking.h96884357.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](https://images.trvl-media.com/lodging/96000000/95480000/95470700/95470643/w508h683x258y0-5fe353a7.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)

### Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

[](https://www.expedia.com/Boston-Hotels-Boston-2bd-King-Bed-Near-Harvard.h95470643.Hotel-Information)

Ward Two

9.8/10

Exceptional

(19 reviews)

"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.

$297 nightly

$332 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Boston-2bd-King-Bed-Near-Harvard.h95470643.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)

![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)

![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

(58 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.

$313 nightly

$350 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Salem-Hotels-Downtown-Salem-Park-Play-Modern-3-Bedroom.h72612302.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/a6fed9c9.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)

![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

(1 review)

"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.

$371 nightly

$415 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Charming-2-Bedroom-Condo-In-Delightful-Chelsea-With-WiFi.h115817302.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)

![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)

![Interior](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/a17d20b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*New 2BR Downtown Attraction| Salem+Beverly|Witch

[](https://www.expedia.com/Boston-Hotels-NEW-Spacious-2BrDowntownBeverlySalemParking.h68769097.Hotel-Information)

Beverly

10/10

Exceptional

(32 reviews)

"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.

$323 nightly

$361 total

Feb 18 - Feb 19

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-NEW-Spacious-2BrDowntownBeverlySalemParking.h68769097.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)

![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)

![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)

### 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.

$428 nightly

$450 total

Feb 28 - Mar 1

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)

![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)

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

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

Wakefield

10/10

Exceptional

(5 reviews)

"Great stay"

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

Alex c.

$330 nightly

$369 total

Feb 18 - Feb 19

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21320000/21318100/21318003/007ceb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

[](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.

$377 nightly

$433 total

Feb 10 - Feb 11

Total with taxes and fees

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

![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)

![Interior](https://images.trvl-media.com/lodging/36000000/35360000/35353800/35353788/afaef89d.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)

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

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

Everett

10/10

Exceptional

(30 reviews)

"Great location! Host was very attentive. Enjoyed our stay."

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

Kim H.

$323 nightly

$361 total

Feb 9 - Feb 10

Total with taxes and fees

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

![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)

### 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.

$189 nightly

$211 total

Feb 9 - Feb 10

Total with taxes and fees

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

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/119000000/118250000/118243900/118243862/a6f6e036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Miscellaneous](https://images.trvl-media.com/lodging/119000000/118250000/118243900/118243862/1db2203b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/119000000/118250000/118243900/118243862/0dbb08ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern & Cozy 3-Bedroom Condo near Downtown

[](https://www.expedia.com/Boston-Hotels-Modern-Cozy-3-Bedroom-Condo-Near-Downtown.h118243862.Hotel-Information)

Roxbury

10/10

Exceptional

(8 reviews)

"One of the most cleanest places we’ve ever stayed!"

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

Seetharaman S.

$344 nightly

$396 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Modern-Cozy-3-Bedroom-Condo-Near-Downtown.h118243862.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)

![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)

![TV](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/90be1e7c.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.

$225 nightly

$251 total

Feb 22 - Feb 23

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](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/da52403c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/786d5023.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/a13661ee.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.

$554 nightly

$593 total

Feb 9 - Feb 10

Total with taxes and fees

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

![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)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/97000000/96740000/96735900/96735817/w509h683x257y0-dfaaed96.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)

### 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.

$349 nightly

$390 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Downtown-Salem-Chic.h96735817.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)

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

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

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

[](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.

$388 nightly

$446 total

Feb 17 - Feb 18

Total with taxes and fees

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

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

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

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/113000000/112640000/112637400/112637397/96a75d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112640000/112637400/112637397/55951bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Jamaica Plain

9.2/10

Wonderful

(9 reviews)

"Great place ideally located."

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

Dennis M.

$319 nightly

$367 total

Feb 12 - Feb 13

Total with taxes and fees

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

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

![Dining](https://images.trvl-media.com/lodging/79000000/78480000/78474400/78474311/b2011887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78480000/78474400/78474311/c88edbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Lovely Two Bedroom Condo in South Boston

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

South Boston

7.8/10

Good

(6 reviews)

"Very clean "

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

Paul A.

$450 nightly

$487 total

Feb 9 - Feb 10

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/7b35e7cf.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)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/6d0631d4.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

$444 nightly

$510 total

Feb 9 - Feb 10

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Eastie-Gem-Taste-Of-Local-Life-By-The-Waterfront.h122110307.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=2026-02-22&endDate=2026-02-23&regionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Apartments

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Aparthotels

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Condos

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America&regionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=HOUSE_BOAT)

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## Top Winchester Hotel Reviews

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

### The Revolution Hotel

10/10 Excellent

"I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would definitely stay here again."

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

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

### Hilton Boston Park Plaza

10/10 Excellent

"Great stay!"

[](https://expedia.com/Boston-Hotels-Boston-Park-Plaza.h4215.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

"The staff was extremely friendly and accommodating. The decor was beautiful. The room was very clean and comfortable. "

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

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

### Hilton Boston Logan Airport

10/10 Excellent

"Cheaper than parking great service and sccomodations!"

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

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

### Harborside Inn Of Boston

10/10 Excellent

"Best price for the location! Always clean and great staff!"

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

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

### Encore Boston Harbor

10/10 Excellent

"Wonderful service, gorgeous room"

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

![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg)

### Seaport Hotel Boston

10/10 Excellent

"Beautiful hotel, excellent staff and really nice location."

[](https://expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information)

![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg)

### citizenM Boston Back Bay

10/10 Excellent

"Clean room. Great staff!"

[](https://expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information)

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

### Omni Boston Hotel at the Seaport

10/10 Excellent

"The room looked amazing and the staff was very nice"

[](https://expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information)

## Find out more about Winchester

## Winchester Condo Rentals information

| Number of reviews | 375               |
| ----------------- | ----------------- |
| Accommodation     | 172 Condo Rentals |
| Lowest Price      | $211              |
| Highest Price     | $593              |

## 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?

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- [Woburn Vacation Rentals ](https://www.expedia.com/Woburn-Vacation-Rentals.d10373.Travel-Guide-VacationRentals)

- [Things to do in Woburn ](https://www.expedia.com/Things-To-Do-In-Woburn.d10373.Travel-Guide-Activities)