A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Winchester condo rentals

Smart TV, fireplace

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

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
$202 nightly
The price is $226
Jun 30 - Jul 1
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Exterior detail

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Beacon Hill
9.6 out of 10, Exceptional, (9 reviews)
"Great location!"
United States
Lea M.
$294 nightly
The price is $338
Jul 6 - Jul 7
Total with taxes and fees
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Microwave, oven, stovetop, dishwasher

Adorable 1-bedroom apartment in welcoming Cambridge

Adorable 1-bedroom apartment in welcoming Cambridge
North Cambridge
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay in Cambridge for the Boston marathon. Walking distance to the red line and busses made it very easy to get downtown. This place had everything you could think of to make it a comfortable stay, and the host had excellent communication. Would stay here again!"
United States
Peter C.
$301 nightly
The price is $344
Jun 30 - Jul 1
Total with taxes and fees
Adorable 1-bedroom apartment in welcoming Cambridge
Outdoor dining

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (84 reviews)
"Host was amazing and responded right away with any questions or concerns we had! Beautiful place to stay!"
United States
Amy I.
$322 nightly
The price is $370
Jul 14 - Jul 15
Total with taxes and fees
🎖The Boiler Room - Close to Subway & Downtown🎖
Marina

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
9.8 out of 10, Exceptional, (74 reviews)
"Great location, clean and comfortable, responsive host. Overall, a terrific stay. "
United States
Tiffany F.
$252 nightly
The price is $281
Jul 7 - Jul 8
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Exterior

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.4 out of 10, Very Good, (6 reviews)
"Beautiful house & views,"
United States
Suzanne P.
$564 nightly
The price is $604
Jun 30 - Jul 1
Total with taxes and fees
Coastal Charm: Lobster Châto
Smart TV

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston
stoneham
9.0 out of 10, Wonderful, (10 reviews)
"Stayed at this property for a little over a week. Property is in good shape, location is convenient. Host is very responsive to questions. Highly recommend this property"
United States
Brendan D.
$514 nightly
The price is $544
Jul 5 - Jul 6
Total with taxes and fees
Modern Three Bedroom Condo - Near Boston
3 bedrooms, desk, iron/ironing board, free WiFi

Modern & Cozy 3-Bedroom Condo near Downtown

Modern & Cozy 3-Bedroom Condo near Downtown
Roxbury
10.0 out of 10, Exceptional, (10 reviews)
"One of the most cleanest places we’ve ever stayed!"
United States
Seetharaman S.
$377 nightly
The price is $433
Jun 30 - Jul 1
Total with taxes and fees
Modern & Cozy 3-Bedroom Condo near Downtown
Exterior detail

Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Marblehead Historic District
10.0 out of 10, Exceptional, (8 reviews)
$251 nightly
The price is $281
Jul 7 - Jul 8
Total with taxes and fees
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Interior

Modern, Spacious Condo, minutes to downtown Salem, Private Parking on Site!

Modern, Spacious Condo, minutes to downtown Salem, Private Parking on Site!
Salem
10.0 out of 10, Exceptional, (12 reviews)
"Great stay in Salem!"
United States
Ashley
$431 nightly
The price is $482
Jun 30 - Jul 1
Total with taxes and fees
Modern, Spacious Condo, minutes to downtown Salem, Private Parking on Site!
Dining

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

Your cozy home away from home, close to subway and downtown Boston
Jamaica Plain
9.6 out of 10, Exceptional, (14 reviews)
"Great place ideally located."
Australia
Dennis M.
$360 nightly
The price is $414
Jul 12 - Jul 13
Total with taxes and fees
Your cozy home away from home, close to subway and downtown Boston
Smart TV

Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Salem
9.8 out of 10, Exceptional, (11 reviews)
"Great location, very good communication, had everything we needed for our stay over Halloween! We had a wonderful time. "
United States
Robin P.
$329 nightly
The price is $368
Jun 30 - Jul 1
Total with taxes and fees
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
TV, offices

Family-Friendly Salem Apt: Near Dtwn Sites!

Family-Friendly Salem Apt: Near Dtwn Sites!
Salem
10.0 out of 10, Exceptional, (39 reviews)
"House was impeccably clean and designed so beautifully. The location was a quiet little street full of lovely historic homes. The beds were so comfortable! Joe was a super nice and responsive host and helped us out when our flight got changed and our arrival time was several hours earlier than expected. We truly enjoyed our stay here."
United States
Sarah
$586 nightly
The price is $670
Jul 7 - Jul 8
Total with taxes and fees
Family-Friendly Salem Apt: Near Dtwn Sites!
Smart TV, books

Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail
Downtown Boston
10.0 out of 10, Exceptional, (56 reviews)
"Amazing Place, Central, Beautiful.Could not have asked for anything more.REMARKABLE!!!!!!!!!!!!!!!!!!!!!!!!"
United States
Laz A.
$421 nightly
The price is $484
Jul 26 - Jul 27
Total with taxes and fees
Bright & Spacious Loft Steps to the Freedom Trail
Fridge, microwave, oven, stovetop

Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
Wakefield
9.6 out of 10, Exceptional, (8 reviews)
"Great stay"
United States
Alex c.
$504 nightly
The price is $563
Jul 27 - Jul 28
Total with taxes and fees
Stylish home next to train to Boston, near Salem
Fridge, microwave, oven, stovetop

🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (60 reviews)
"Is a great place"
United States
Ramon G.
$476 nightly
The price is $547
Jul 6 - Jul 7
Total with taxes and fees
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Interior

2 bedroom condo walking distance to downtown, free parking

2 bedroom condo walking distance to downtown, free parking
Salem
10.0 out of 10, Exceptional, (1 review)
"Please was clean and as listed with an easy walk to town. The Black Cat diner across the street was a cool experience too."
United States
Tracey
$297 nightly
The price is $332
Jun 29 - Jun 30
Total with taxes and fees
2 bedroom condo walking distance to downtown, free parking
Smart TV, video games, computer monitors, printers

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.8 out of 10, Excellent, (5 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
Amna S.
$395 nightly
The price is $441
Jul 20 - Jul 21
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Interior

Chic Downtown Salem 3 Bedroom w/ Parking

Chic Downtown Salem 3 Bedroom w/ Parking
Salem
10.0 out of 10, Exceptional, (11 reviews)
"Check in went very smooth and kitchen was well stocked with everything needed."
United States
Justin R.
$417 nightly
The price is $465
Jun 28 - Jun 29
Total with taxes and fees
Chic Downtown Salem 3 Bedroom w/ Parking
Fridge, microwave, oven, stovetop

Lg suite for up to 8 ppl/3 floor

Lg suite for up to 8 ppl/3 floor
Dorchester
9.6 out of 10, Exceptional, (16 reviews)
"Property was secure and had a fantastic location.The owner was very friendly and gave so much great information about the area. Would absolutely book again!"
Canada
blake s.
$342 nightly
The price is $393
Jul 5 - Jul 6
Total with taxes and fees
Lg suite for up to 8 ppl/3 floor
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.
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Top Winchester Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"The room was clean and the bed was very comfortable. The hotel is also a close distance from the Hanover Theater and Fenway Park."
Brieanna 1-night trip
Posted less than an hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
358
Accommodation
169 Condo Rentals
Lowest Price
$226
Highest Price
$670

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from $226 to $670 per night. These properties offer loads of space for the whole family at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winchester?
Take your pick of 169 condos in Winchester. No matter if you're traveling with the kids or planning a weekend escape with your buddies, Expedia will help you find the right space for your entire crew.
Why book your condo in Winchester with Expedia?
Booking a condo in Winchester is as simple as deciding on your travel dates and selecting an option that satisfies your needs. Seeking something upscale or budget friendly, or a stay that also features a laundry and kitchen? Use Expedia's search filters to further narrow your search results and find the ideal fit at the right price.
How can I find cheap condos in Winchester?
A great way to locate cheap condos in Winchester is with Expedia's handy filter tool. Refine your search by star rating, amenities and budget to access awesome rates in a few clicks.
What is there to do in Winchester near my condo?
The most useful travel accessory is a well-planned itinerary. Winter Pond is a terrific place to kick-start your adventures in Winchester.

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