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Search and Rent Winchester Condos

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Our top choices for Winchester condo rentals

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

Condo in Beacon Hill

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
$238 nightly
The price is $274
Dec 31 - Jan 1, 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

Condo in Marblehead

Charming 1-bedroom condo in marvelous Marblehead with hidden patio
2.0 star property
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.
$144 nightly
The price is $161
Dec 23 - Dec 24
Total with taxes and fees
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Property grounds
*NEW Downtown Getaway|2BR|Salem+Beverly|Parking

Condo in Beverly

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

Condo in Downtown Boston

Bright & Spacious Loft Steps to the Freedom Trail
10.0 out of 10, Exceptional, (52)
"Spacious condo, perfect location, and exceptional hospitality from mangers."
United States
Robert S.
$329 nightly
The price is $378
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 ♥

Condo in Marblehead

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
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.
$196 nightly
The price is $219
Dec 23 - Dec 24
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Smart TV
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking

Condo in Ward Two

Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
9.8 out of 10, Exceptional, (19)
"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.
$299 nightly
The price is $334
Dec 23 - Dec 24
Total with taxes and fees
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Interior
Downtown Salem - Park & Play Modern 3 Bedroom

Condo in Salem

Downtown Salem - Park & Play Modern 3 Bedroom
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
Fridge, microwave, oven, stovetop
Stylish home next to train to Boston, near Salem

Condo in Wakefield

Stylish home next to train to Boston, near Salem
2.0 star property
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.
$348 nightly
The price is $389
Jan 13 - Jan 14, 2026
Total with taxes and fees
Stylish home next to train to Boston, near Salem
Fridge, microwave, oven, stovetop
Spacious 3BR Salem Getaway, Modern & Walkable

Condo in Salem

Spacious 3BR Salem Getaway, Modern & Walkable
10.0 out of 10, Exceptional, (6)
"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.
$270 nightly
The price is $301
Dec 23 - Dec 24
Total with taxes and fees
Spacious 3BR Salem Getaway, Modern & Walkable
Smart TV
Modern Three Bedroom Condo - Near Boston

Condo in stoneham

Modern Three Bedroom Condo - Near Boston
9.0 out of 10, Wonderful, (9)
"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
Meghan D.
$425 nightly
The price is $447
Dec 23 - Dec 24
Total with taxes and fees
Modern Three Bedroom Condo - Near Boston
Smart TV, computer monitors, printers
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Condo in Chelsea

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
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.
$382 nightly
The price is $427
Dec 23 - Dec 24
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Dining
Lg suite for up to 8 ppl/2 floor

Condo in Dorchester

Lg suite for up to 8 ppl/2 floor
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
Smart TV, fireplace
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Condo in Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. 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
Dec 28 - Dec 29
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

Condo in Beverly

Modern 2-bedroom condo 1 mile to Salem
2.0 star property
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.
$353 nightly
The price is $394
Dec 23 - Dec 24
Total with taxes and fees
Modern 2-bedroom condo 1 mile to Salem
Dining
*1710 Historic Downtown Salem|2BR Retreat|Parking

Condo in Downtown Salem

*1710 Historic Downtown Salem|2BR Retreat|Parking
10.0 out of 10, Exceptional, (60)
"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.
$383 nightly
The price is $438
Dec 26 - Dec 27
Total with taxes and fees
*1710 Historic Downtown Salem|2BR Retreat|Parking
Smart TV, computer monitors
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Condo in Everett

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
10.0 out of 10, Exceptional, (30)
"Great location! Host was very attentive. Enjoyed our stay."
United States
Kim H.
$374 nightly
The price is $418
Jan 13 - Jan 14, 2026
Total with taxes and fees
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Exterior
Coastal Charm: Lobster Châto

Condo in Swampscott

Coastal Charm: Lobster Châto
2.0 star property
8.4 out of 10, Very Good, (6)
"Beautiful house & views,"
United States
Suzanne P.
$610 nightly
The price is $656
Jan 9 - Jan 10, 2026
Total with taxes and fees
Coastal Charm: Lobster Châto
Interior
Modern & Stylish 1-Bedroom Condo near Downtown

Condo in Roxbury

Modern & Stylish 1-Bedroom Condo near Downtown
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

Condo in East Boston

Eastie Gem: Taste of local life by the waterfront, airport and train
2.0 star property
$377 nightly
The price is $434
Dec 25 - Dec 26
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🎖

Condo in Dorchester

🎖The Ashmont Suite - Close to Subway + Downtown🎖
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🎖
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 Langham, Boston

The Langham, Boston

10/10 Excellent
"Beautiful weekend stay during the weekend before Christmas. Everyone there was so accommodating and they treated our boys like VIP guests. I would 100% go there again. Thank you Langham for giving us a memorable family weekend getaway! "
Ashley 2-night trip
Posted 19 hours ago
The Langham, Boston

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
415
Accommodation
172 Condo Rentals
Lowest Price
$161
Highest Price
$656

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from $161 to $656 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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