Search Condo Rentals in Winchester

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Compare 158 Condo Rentals in Winchester with updated reviews, rates, and availability.

Convenient and Charming 2-bedroom condo with Private Parking, in South Boston
2.0 star property
5.4 out of 10, (6)
"Really nice 2 bed/2 bath unit in a good neighborhood just steps from the beach which was great for going on runs in the morning. Also less than 10min walk to a cute little neighborhood with bars/restaurants and convenience stores. Less than 10 min uber right to the convention center. Overall really suited our needs for attending a conference at a MUCH better price than you could get from any of the hotels. My only critiques are that the check-in instructions were in accurate regarding location...
The price is SAR 451
SAR 958 total
includes taxes & fees
3 Dec - 4 Dec
Convenient and Charming 2-bedroom condo with Private Parking, in South Boston
Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!
2.0 star property
9.4 out of 10, Exceptional, (3)
"We had difficulty finding a place to host our family of (5) comfortably and had 2 bathrooms. This house was just that and more! We enjoyed being able to cook some of our meals in the fully stocked kitchen, even baked cookies, and relaxed and watched a movie in the Family Room. The location is outstanding, walking distance to a lot of places. The grocery store is only 3 minutes away walking! Tim was prompt to respond; answered all my questions and made the check-in process easy. Thanks Tim...
Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!
Excellent 2 bedroom condo in South Boston
10.0 out of 10, Exceptional, (17)
"Convenient location close to the train station for access to downtown. Safe area, also close to park and beach. Unit was very clean and had everything needed. Dryer takes a little long but that's typical with all-in-one units. No designated parking if you have a car but was able to find close street parking."
Excellent 2 bedroom condo in South Boston
3 story penthouse with the best views of the Boston Skylines
8.6 out of 10, Excellent, (14)
"Great location, great view of the city. All of us slept great. Other than having wrong code to get in, which was quickly rectified the stay was great and would stay there again."
3 story penthouse with the best views of the Boston Skylines
Suite at House of L: near Boston, Hospitals, Encore Casino, Beautiful Garden, Fast WiFi, Driveway
9.0 out of 10, Wonderful, (20)
"Great experience "
Suite at House of L: near Boston, Hospitals, Encore Casino, Beautiful Garden, Fast WiFi, Driveway
*Historic1710 2Br-Sleeps 7 Halloween|Salem|Parking
10.0 out of 10, Exceptional, (30)
"Amazing! We loved the property. We could walk to everything. The condo had so much charm and was nicely decorated. The beds were very comfortable. The host was easy to communicate with and they did an awesome job decorating for Halloween. We would definitely stay again"
The price is SAR 556
SAR 1,275 total
includes taxes & fees
11 Dec - 12 Dec
*Historic1710 2Br-Sleeps 7 Halloween|Salem|Parking
Downtown Salem - Park & Play Modern 3 Bedroom
10.0 out of 10, Exceptional, (35)
"Clean, everything you need. Quiet neighborhood. We could walk everywhere. Fun trip with family."
The price is SAR 886
SAR 1,778 total
includes taxes & fees
25 Nov - 26 Nov
Downtown Salem - Park & Play Modern 3 Bedroom
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
10.0 out of 10, Exceptional, (9)
"Clean and comfortable central Cambridge/Somerville location. Well-stocked kitchen and bathroom staples for normal habitation—ample toilet paper in the bathroom! The details matter!"
The price is SAR 828
SAR 1,633 total
includes taxes & fees
25 Nov - 26 Nov
Boston 2bd King Bed near Harvard, MIT, subway near Boston. On-site free Parking
Salem Haunted Happenings Retreat 1bd w/ Private Parking
10.0 out of 10, Exceptional, (5)
"This place was great! Walking distance to all of the main attractions and the place was perfect for two people! "
The price is SAR 372
SAR 784 total
includes taxes & fees
8 Dec - 9 Dec
Salem Haunted Happenings Retreat 1bd w/ Private Parking
New Luxury Renovation | near T
9.8 out of 10, Exceptional, (8)
"The unit was spotlessly clean. The location was good with the T line a short walk away. Communication was excellent. Overall, we were all very pleased with the accommodations. Would definitely recommend. "
New Luxury Renovation | near T
★Downtown Condo~Steps from the Water & Common★
10.0 out of 10, Exceptional, (39)
"We had a lovely stay in Salem. It was perfect for the pets, plenty of nearby places to walk the dog and a backyard. It was convenient to many of the places we came to Salem to see. Owner was very communicative and helpful. Would stay here again. "
The price is SAR 413
SAR 1,007 total
includes taxes & fees
4 Dec - 5 Dec
★Downtown Condo~Steps from the Water & Common★
Coastal Charm: Lobster Châto
2.0 star property
7.0 out of 10, Good, (2)
"My husband and i loved the ocean front views and sounds and walk on the beach in the morning The location was great close to salem and marblehead a beautiful little town . The place was clean and we loved the eclectic antique style and furnishings that were super comfortable also love the big wood burning fireplace..our Host was top notch immediate response and care for whatever you needed made for a great experience. Also briefly met the owner such a really nice person . We will stay again "
The price is SAR 1,164
SAR 2,753 total
includes taxes & fees
24 Nov - 25 Nov
Coastal Charm: Lobster Châto
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
9.4 out of 10, Exceptional, (79)
"Space was comfortable, affordable, and well-located close to public transit to downtown"
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
🎖The Ashmont Suite - Close to Subway + Downtown🎖
10.0 out of 10, Exceptional, (36)
"The suite is in a beautifully restored old home with two other suites. Ours was in the top section of the home which required moving suitcases up quite a few steps. Parking is on a busy road and there is only enough space for two cars in front of the house, which might require carrying lugguage a bit further. Other than that it was a really nice place to stay."
The price is SAR 747
SAR 1,450 total
includes taxes & fees
15 Dec - 16 Dec
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Beautiful New Renovation | near T
9.0 out of 10, Wonderful, (4)
"Great experience. Perfect for what we wanted to do."
Beautiful New Renovation | near T
Super Convenience 2BR Condo W/Private Parking in Newton
10.0 out of 10, Exceptional, (26)
"It was an awesome VRBO. "
Super Convenience 2BR Condo W/Private Parking in Newton
Historic Somerville Cambridge 1 Bed, Inman Square
6.0 out of 10, (3)
"The property was okay, but not great. The check-in process was completely lacking, I called, emailed and texted every number I could find with no response until around 6 pm on check-in day. The basic supplies in the kitchen and bathroom were lacking or non-existent and the second 'bed', an air mattress leaked badly."
Historic Somerville Cambridge 1 Bed, Inman Square
In the heart of the historic district
10.0 out of 10, Exceptional, (33)
"We had an absolutely wonderful stay at this property in Marblehead, MA. The host was incredibly kind, with great communication throughout our stay. They even provided us with fantastic tips on places to eat, which made our experience even better. The property itself was perfect—an excellent location just steps away from charming boutiques, a cozy cafe, a delightful toy store, and the picturesque coastline. The town of Marblehead is quaint, quiet, and peaceful, offering a serene escape from the...
In the heart of the historic district
Rehabbed 3BR2Bth, parking, Cambridge/Boston
2.0 star property
9.6 out of 10, Exceptional, (7)
"Beautiful place, Target store and other stores are next door. Responsive host, clean apartment. Lovely view. Be ready for the steep climb up and down the stairs, especially if you are given the third floor. I’ll definitely book this again. "
The price is SAR 788
SAR 1,916 total
includes taxes & fees
25 Nov - 26 Nov
Rehabbed 3BR2Bth, parking, Cambridge/Boston
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
2.0 star property
8.0 out of 10, Very Good, (3)
"Need to advertise there is upstair occupents and parking is in the street also second bedroom is a hide a bed. "
The price is SAR 477
SAR 969 total
includes taxes & fees
3 Dec - 4 Dec
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
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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Other property types in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
7.4 out of 10, Good, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (493)
"We enjoyed our stay. It was walkable to Chinatown. Very accessible to subway station. We liked that our room was on the top floor. "
The price is SAR 484
SAR 1,015 total
includes taxes & fees
25 Nov - 26 Nov
Global Luxury Suites Downtown Boston
Maverick Suites at 28 Fenway
3.0 star property
9.0 out of 10, Wonderful, (152)
"Everything good "
The price is SAR 396
SAR 823 total
includes taxes & fees
22 Dec - 23 Dec
Maverick Suites at 28 Fenway
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.

Frequently asked questions

How much do condos in Winchester cost?
Prepare to pay from SAR 372 to SAR 1,164 per night for condos in Winchester. No matter your budget, you’ll find the perfect stay on Expedia. 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?
Pick from 158 condos in Winchester. No matter if you’re taking a trip with the family or getting away with your pals, Expedia can help you find the ideal base for your crew.
Why book your condo in Winchester with Expedia?
With Expedia, it’s a cinch to find your dream condo in Winchester. Looking for an upmarket stay? Try out our filters to search for properties that have a 5-star rating. If you’re sticking to a budget, choose how much you want to spend and then browse our fabulous deals. We’ll help you find the perfect stay whatever your getaway looks like.
How can I find cheap condos in Winchester?
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