Search and Rent Winchester Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winchester condo rentals

♥ 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, (73 reviews)
"Great location, clean and comfortable, responsive host. Overall, a terrific stay. "
United States
Tiffany F.
$253 nightly
The price is $283
May 18 - May 19
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

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, (4 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
$191 nightly
The price is $213
May 14 - May 15
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

🎖The Boiler Room - Close to Subway & Downtown🎖

🎖The Boiler Room - Close to Subway & Downtown🎖
Dorchester
9.8 out of 10, Exceptional, (77 reviews)
"Beautiful property and rooms. "
Canada
Dawn W.
🎖The Boiler Room - Close to Subway & Downtown🎖

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.
$545 nightly
The price is $583
May 18 - May 19
Total with taxes and fees
Coastal Charm: Lobster Châto

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, (4 reviews)
"Darling apartment - perfectly located close to shops and restaurants in downtown Marblehead. "
United States
Lauren P.
$244 nightly
The price is $272
May 11 - May 12
Total with taxes and fees
Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Everett
10.0 out of 10, Exceptional, (31 reviews)
"We had a great stay& the beds are so comfortable."
United States
Mitchell P.
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Family-Friendly Salem Apt: Near Dtwn Sites!

Family-Friendly Salem Apt: Near Dtwn Sites!
Salem
10.0 out of 10, Exceptional, (37 reviews)
"Very nice, clean & comfortable accommodations, just like home! Close to everything in Salem, very quiet neighborhood. We're grateful and enjoyed our stay!"
United States
Jan E.
$486 nightly
The price is $556
May 17 - May 18
Total with taxes and fees
Family-Friendly Salem Apt: Near Dtwn Sites!

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.
$505 nightly
The price is $534
May 18 - May 19
Total with taxes and fees
Modern Three Bedroom Condo - Near Boston

Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
Wakefield
9.4 out of 10, Exceptional, (6 reviews)
"Great stay"
United States
Alex c.
$477 nightly
The price is $532
May 11 - May 12
Total with taxes and fees
Stylish home next to train to Boston, near Salem

Adorable 1-bedroom apartment in welcoming Cambridge

Adorable 1-bedroom apartment in welcoming Cambridge
North Cambridge
10.0 out of 10, Exceptional, (2 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.
$273 nightly
The price is $312
May 31 - Jun 1
Total with taxes and fees
Adorable 1-bedroom apartment in welcoming Cambridge

2 bedroom condo walking distance to downtown, free parking

2 bedroom condo walking distance to downtown, free parking
Salem
$294 nightly
The price is $328
May 11 - May 12
Total with taxes and fees
2 bedroom condo walking distance to downtown, free parking

Downtown Salem Chic - 3 Bedroom w/ Parking

Downtown Salem Chic - 3 Bedroom w/ Parking
Salem
10.0 out of 10, Exceptional, (5 reviews)
"Check in went very smooth and kitchen was well stocked with everything needed."
United States
Justin R.
$369 nightly
The price is $412
May 11 - May 12
Total with taxes and fees
Downtown Salem Chic - 3 Bedroom w/ Parking

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

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
10.0 out of 10, Exceptional, (3 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.
$386 nightly
The price is $431
May 13 - May 14
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Downtown Salem - Park & Play Modern 3 Bedroom

Downtown Salem - Park & Play Modern 3 Bedroom
Salem
10.0 out of 10, Exceptional, (67 reviews)
"This was a truly wonderful property - clean, generously stocked, perfect location and attentive owner"
United States
Valerie G.
$367 nightly
The price is $410
May 12 - May 13
Total with taxes and fees
Downtown Salem - Park & Play Modern 3 Bedroom

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
9.2 out of 10, Wonderful, (10 reviews)
"Great place ideally located."
Australia
Dennis M.
$383 nightly
The price is $440
May 11 - May 12
Total with taxes and fees
Your cozy home away from home, close to subway and downtown Boston

Modern & Stylish 1-Bedroom Condo near Downtown

Modern & Stylish 1-Bedroom Condo near Downtown
Roxbury
10.0 out of 10, Exceptional, (5 reviews)
"Very nice and quiet neighborhood. Would love to rent again if the opportunity presents itself. "
United States
Bobby B.
$376 nightly
The price is $432
May 21 - May 22
Total with taxes and fees
Modern & Stylish 1-Bedroom Condo near Downtown

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)
"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
Mallory M.
$485 nightly
The price is $542
May 11 - May 12
Total with taxes and fees
Modern, Spacious Condo, minutes to downtown Salem, Private Parking on Site!

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, (10 reviews)
"Great location, very good communication, had everything we needed for our stay over Halloween! We had a wonderful time. "
United States
Robin P.
$326 nightly
The price is $364
May 12 - May 13
Total with taxes and fees
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

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

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Ward Two
10.0 out of 10, Exceptional, (21 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
Eric D.
$430 nightly
The price is $480
May 24 - May 25
Total with taxes and fees
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail
Downtown Boston
10.0 out of 10, Exceptional, (54 reviews)
"Amazing Place, Central, Beautiful.Could not have asked for anything more.REMARKABLE!!!!!!!!!!!!!!!!!!!!!!!!"
United States
Laz A.
$436 nightly
The price is $501
May 24 - May 25
Total with taxes and fees
Bright & Spacious Loft Steps to the Freedom Trail
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
308
Accommodation
177 Condo Rentals
Lowest Price
$213
Highest Price
$583

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from $213 to $583 per night. These properties offer loads of space for the whole family at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Winchester?
Take your pick of 177 condos in Winchester. No matter if you're traveling with the kids or planning a weekend escape with your buddies, Expedia will help you find the right space for your entire crew.
Why book your condo in Winchester with Expedia?
Booking a condo in Winchester is as simple as deciding on your travel dates and selecting an option that satisfies your needs. Seeking something upscale or budget friendly, or a stay that also features a laundry and kitchen? Use Expedia's search filters to further narrow your search results and find the ideal fit at the right price.
How can I find cheap condos in Winchester?
A great way to locate cheap condos in Winchester is with Expedia's handy filter tool. Refine your search by star rating, amenities and budget to access awesome rates in a few clicks.
What is there to do in Winchester near my condo?
The most useful travel accessory is a well-planned itinerary. Winter Pond is a terrific place to kick-start your adventures in Winchester.

Explore a world of travel with Expedia