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)

## Check prices for these dates

In two weeks

[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 two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester condo rentals

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/58691629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/a0975d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122600000/122591900/122591889/dcd26c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

### 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.

$256 nightly

$294 total

Mar 21 - Mar 22

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)

![Property grounds](https://images.trvl-media.com/lodging/69000000/68770000/68769100/68769097/973ca28c.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)

![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)

### \*2BR Downtown Witch House|Salem+Beverly|Hospitals

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

Beverly

10/10

Exceptional

(33 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.

$301 nightly

$336 total

Mar 18 - Mar 19

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107990000/107987000/107986920/cdcf00d9.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.

$521 nightly

$556 total

Mar 18 - Mar 19

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/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)

![Exterior](https://images.trvl-media.com/lodging/107000000/106890000/106882600/106882526/c3c47455.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.

$345 nightly

$385 total

Mar 20 - Mar 21

Total with taxes and fees

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

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

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114550000/114550000/114549922/1c623532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

[](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.

$190 nightly

$212 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)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/79000000/78070000/78069400/78069315/3ee4a137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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/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.

$471 nightly

$498 total

Mar 21 - Mar 22

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/22000000/21310000/21301300/21301292/34f7d1af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/22000000/21310000/21301300/21301292/157d62e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/22000000/21310000/21301300/21301292/b759d1f0.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/22000000/21310000/21301300/21301292/23ae2928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lg suite for up to 8 ppl/3 floor

[](https://www.expedia.com/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl3-Floor.h21301292.Hotel-Information)

Dorchester

9.6/10

Exceptional

(16 reviews)

"We enjoyed our time at the Guesthouse. The place was clean, comfortable and spacious. Muny was always very responsive. We would definitely stay here again if we return to Boston. "

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

Melanie E.

$403 nightly

$463 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Lg-Suite-For-Up-To-8-Ppl3-Floor.h21301292.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)

![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)

![Interior](https://images.trvl-media.com/lodging/40000000/39540000/39536400/39536322/c04cfe85.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)

### 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.

$310 nightly

$356 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)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/a0dfcd08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ♥ 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.

$229 nightly

$256 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)

![Interior](https://images.trvl-media.com/lodging/97000000/96740000/96735900/96735817/w903h683x60y0-60fc025a.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)

![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)

![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.

$332 nightly

$370 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Downtown-Salem-Chic.h96735817.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/110000000/109550000/109549400/109549335/68d68b59.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)

![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.

$745 nightly

$854 total

Apr 6 - Apr 7

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/105000000/104950000/104940600/104940575/da352403.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)

![Interior](https://images.trvl-media.com/lodging/105000000/104950000/104940600/104940575/a725697d.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)

### 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.

$434 nightly

$485 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Modern.h104940575.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)

![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72612400/72612302/b790839c.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)

### 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

(61 reviews)

"Great location! We walked everywhere. Very clean, comfortable beds, and well stocked with things we needed. "

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

Lisa W.

$320 nightly

$357 total

Mar 18 - Mar 19

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)

![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)

![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

(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.

$395 nightly

$441 total

Mar 18 - Mar 19

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121280000/121274600/121274557/29adffae.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)

### 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 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Charming-1-Bedroom-Condo-In-Marvelous-Marblehead-With-Hidden-Patio.h121274557.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884362/5321ace6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, offices](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884362/410de8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884362/37e88a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/97000000/96890000/96884400/96884362/5d69fca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### \*3BR Downtown Hocus Pocus|Parking|Salem+Beverly

[](https://www.expedia.com/Boston-Hotels-3BR-Downtown-Hocus-PocusParkingSalemBeverly.h96884362.Hotel-Information)

Beverly

10/10

Exceptional

(21 reviews)

"Great communication from host and perfectly situated for the family. Great for all of the kid ages and really close to lots of coffee/food. Loved the stay. "

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

Kerry H.

$345 nightly

$385 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-3BR-Downtown-Hocus-PocusParkingSalemBeverly.h96884362.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)

![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/b90fa626.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)

### 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

Mar 23 - Mar 24

Total with taxes and fees

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

![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)

![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)

### 🎖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.

$456 nightly

$524 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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/6d195cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122110400/122110307/6d0631d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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

$460 nightly

$529 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)

![Exterior detail](https://images.trvl-media.com/lodging/125000000/124470000/124467100/124467075/dc18e02c.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)

![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124467100/124467075/d5cd0ab1.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

$363 nightly

$384 total

Mar 18 - Mar 19

Total with taxes and fees

[](https://www.expedia.com/Boston-Hotels-Prestigious-Milton-Designer-Home.h124467075.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=2026-03-31&endDate=2026-04-01&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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Aparthotels

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Apartments

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Condos

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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=2026-06-15&d1=2026-06-15&endDate=2026-06-18&d2=2026-06-18&lodging=COTTAGE)

Houseboats

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## Top Winchester Hotel Reviews

![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg)

### Harborside Inn Of Boston

10/10 Excellent

"Beautiful, quiet room, very comfortable bed and amazing staff. Very close to restaurants, tourist attractions and waterfront. Will definitely stay here again."

[](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/a1d3b824_y.jpg)

### Encore Boston Harbor

10/10 Excellent

"Location was great enjoyed the stay will be back"

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

![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg)

### The Midtown Hotel MOD Collection by Sonesta

8/10 Good

"Room was clean and a great location for access to all parts of Boston."

[](https://expedia.com/Boston-Hotels-Midtown-Hotel.h2898.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

4/10 Poor

"Double charged for my room"

[](https://expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information)

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

### Seaport Hotel Boston

10/10 Excellent

"Great place and staff, location is perfect"

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

![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_y.jpg)

### Omni Boston Hotel at the Seaport

8/10 Good

"Overall 4.75⭐️"

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

"Best hotel you could find in Boston from design to staff friendliness"

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

![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg)

### Omni Parker House 

10/10 Excellent

"Property is great, staff is super friendly and everything is a short walking distance. "

[](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information)

![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9_y.jpg)

### Hilton Boston Logan Airport

8/10 Good

"Extremely convenient when catching an early flight, and it is a Hilton - clean, well staffed, professional and courteous "

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

## Find out more about Winchester

## Winchester Condo Rentals information

| Number of reviews | 374               |
| ----------------- | ----------------- |
| Accommodation     | 172 Condo Rentals |
| Lowest Price      | $212              |
| Highest Price     | $854              |

## Frequently asked questions

### How much do condos in Winchester cost?

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

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