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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Winchester condo rentals

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

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
$243 nightly
The price is $279
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Exterior detail
Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming 1-bedroom condo in marvelous Marblehead with hidden patio
2.0 star property
Marblehead
10.0 out of 10, Exceptional, (2)
"This place is awesome. First time going to the east and I’d rather stay here over any 5 star hotel. Janie is so nice n gave some great suggestions for bars/places to eat while there. The only bad part about the trip was having to go home. Easy parking, fairy tale like back yard area, historic house, and only a 4 minute walk to the ocean. "
United States
Madison J.
$182 nightly
The price is $204
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Exterior
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

*NEW Downtown Getaway|2BR|Salem+Beverly|Parking
Beverly
10.0 out of 10, Exceptional, (32)
"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
Lawrence D.
$262 nightly
The price is $293
Dec 29 - Dec 30
Total with taxes and fees
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking
Smart TV, books
Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail
Downtown Boston
10.0 out of 10, Exceptional, (52)
"Spacious condo, perfect location, and exceptional hospitality from mangers."
United States
Robert S.
$304 nightly
The price is $349
Jan 22 - Jan 23, 2026
Total with taxes and fees
Bright & Spacious Loft Steps to the Freedom Trail
Marina
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

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

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead
10.0 out of 10, Exceptional, (71)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
$240 nightly
The price is $268
Dec 29 - Dec 30
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Interior
Downtown Salem - Park & Play Modern 3 Bedroom

Downtown Salem - Park & Play Modern 3 Bedroom

Downtown Salem - Park & Play Modern 3 Bedroom
Salem
10.0 out of 10, Exceptional, (58)
"This was a truly wonderful property - clean, generously stocked, perfect location and attentive owner"
United States
Valerie G.
$319 nightly
The price is $356
Jan 6 - Jan 7, 2026
Total with taxes and fees
Downtown Salem - Park & Play Modern 3 Bedroom
Exterior
*1710 Historic 2BR |Downtown Salem Retreat|Parking

*1710 Historic 2BR |Downtown Salem Retreat|Parking

*1710 Historic 2BR |Downtown Salem Retreat|Parking
Downtown Salem
10.0 out of 10, Exceptional, (62)
"We had a fantastic time here! The home was so charming and comfortable, and we loved the decor. The location couldn’t be more perfect (we were able to walk to all the sights we wanted to see in Salem), and the hosts are also very communicative. It truly exceeded our expectations. "
United States
Kristin B.
$389 nightly
The price is $445
Jan 2 - Jan 3, 2026
Total with taxes and fees
*1710 Historic 2BR |Downtown Salem Retreat|Parking
Smart TV
Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
2.0 star property
Wakefield
10.0 out of 10, Exceptional, (5)
"we were in Massachusetts for our youngest granddaughters college graduation. This place was great. Good location and great hosts! Beautiful neighborhood Easy to walk to breakfast, lunch or dinner. "
United States
Rebecca Z.
$345 nightly
The price is $385
Jan 25 - Jan 26, 2026
Total with taxes and fees
Stylish home next to train to Boston, near Salem
Outdoor dining
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

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (4)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
$191 nightly
The price is $213
Jan 26 - Jan 27, 2026
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Fridge, microwave, oven, stovetop
Modern 2-bedroom condo 1 mile to Salem

Modern 2-bedroom condo 1 mile to Salem

Modern 2-bedroom condo 1 mile to Salem
2.0 star property
Beverly
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay!! Excellent location with many walking distance food options. Super clean and super cozy!! Hosts were responsive and caring for our comfort while we stayed. Thank you for the snacks!!! We would definitely stay here again!!!"
United States
Melissa G.
$355 nightly
The price is $397
Dec 29 - Dec 30
Total with taxes and fees
Modern 2-bedroom condo 1 mile to Salem
Fridge, microwave, oven, stovetop
Spacious 3BR Salem Getaway, Modern & Walkable

Spacious 3BR Salem Getaway, Modern & Walkable

Spacious 3BR Salem Getaway, Modern & Walkable
Salem
10.0 out of 10, Exceptional, (7)
"We had a great time, all was good. If you get takeout, you may want to make sure you grab salt, pepper, or ketchup packets. Overall we all really enjoyed the accommodations and being a short drive to all the fun sites in Salem."
United States
Tina G.
$276 nightly
The price is $309
Jan 11 - Jan 12, 2026
Total with taxes and fees
Spacious 3BR Salem Getaway, Modern & Walkable
Smart TV, computer monitors, printers
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

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, (1)
"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.
$380 nightly
The price is $425
Dec 29 - Dec 30
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Fridge, microwave, oven, stovetop
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

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, (30)
"Great location! Host was very attentive. Enjoyed our stay."
United States
Kim H.
$381 nightly
The price is $425
Jan 12 - Jan 13, 2026
Total with taxes and fees
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Dining
Lg suite for up to 8 ppl/2 floor

Lg suite for up to 8 ppl/2 floor

Lg suite for up to 8 ppl/2 floor
Dorchester
10.0 out of 10, Exceptional, (12)
"It was a perfect location for our daily plans. The owner was very responsive to our needs "
United States
Mary P.
$412 nightly
The price is $474
Jan 7 - Jan 8, 2026
Total with taxes and fees
Lg suite for up to 8 ppl/2 floor
TV, fireplace
Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
2.0 star property
Swampscott
8.4 out of 10, Very Good, (6)
"Beautiful house & views,"
United States
Suzanne P.
$572 nightly
The price is $613
Dec 29 - Dec 30
Total with taxes and fees
Coastal Charm: Lobster Châto
Interior
Modern & Stylish 1-Bedroom Condo near Downtown

Modern & Stylish 1-Bedroom Condo near Downtown

Modern & Stylish 1-Bedroom Condo near Downtown
Roxbury
10.0 out of 10, Exceptional, (5)
"Very nice and quiet neighborhood. Would love to rent again if the opportunity presents itself. "
United States
Bobby B.
$340 nightly
The price is $391
Jan 1 - Jan 2, 2026
Total with taxes and fees
Modern & Stylish 1-Bedroom Condo near Downtown
Fridge, microwave, oven, stovetop
Eastie Gem: Taste of local life by the waterfront, airport and train

Eastie Gem: Taste of local life by the waterfront, airport and train

Eastie Gem: Taste of local life by the waterfront, airport and train
2.0 star property
East Boston
$377 nightly
The price is $434
Jan 1 - Jan 2, 2026
Total with taxes and fees
Eastie Gem: Taste of local life by the waterfront, airport and train
Fridge, microwave, oven, stovetop
🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (53)
"Great house, perfect for our family of 5. Pretty far from Boston and weekend train service was spotty so spent quite a bit on Uber but other than that, a fantastic stay!"
United States
Alex S.
$450 nightly
The price is $517
Jan 16 - Jan 17, 2026
Total with taxes and fees
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Exterior detail
Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston
South Boston
7.8 out of 10, Good, (6)
"Very clean "
United States
Paul A.
$420 nightly
The price is $453
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lovely Two Bedroom Condo in South Boston
Fridge, microwave, oven, stovetop
Brookline Village, Central Air, 2B, Near Longwood

Brookline Village, Central Air, 2B, Near Longwood

Brookline Village, Central Air, 2B, Near Longwood
Brookline
9.6 out of 10, Exceptional, (63)
"Very clean, good location, good for 2 couples or family. Loved the provided coffee and snacks."
United States
marvin g.
$410 nightly
The price is $426
Dec 29 - Dec 30
Total with taxes and fees
Brookline Village, Central Air, 2B, Near Longwood
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 Revolution Hotel

The Revolution Hotel

10/10 Excellent
"Absolutely amazing probably one of the best rooms I’ve experienced in Boston. I will definitely stay here again."
Jason 1-night trip
Posted 4 hours ago
The Revolution Hotel

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
395
Accommodation
172 Condo Rentals
Lowest Price
$213
Highest Price
$613

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from $213 to $613 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 172 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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