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Compare 200 Condo Rentals in Winchester with updated reviews, rates, and availability.

Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston

8.6 out of 10, Excellent, (141)
"Great location for a weekend trip to visit my son"
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston

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

Convenient and Charming 2-bedroom condo with Private Parking, in South Boston

2.0 star property
5.8 out of 10, (8)
"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 AED 448
AED 950 total
includes taxes & fees
26 Mar - 27 Mar
Convenient and Charming 2-bedroom condo with Private Parking, in South Boston

🎖The Boiler Room - Close to Subway & Downtown🎖

9.8 out of 10, Exceptional, (67)
"Stayed in The Boiler Room downstairs. Ceiling is a bit creaky, could use a grab bar for entering/exiting shower. Otherwise a good place to stay. Transit train is only a 10 min walk, and several restaurants nearby. We recommend Molinari's"
🎖The Boiler Room - Close to Subway & Downtown🎖

The Warlock House: Bewitching - Speak Spells, Wave Wands, Ride Brooms - Walk to Salem, WiFi, Parking

9.8 out of 10, Exceptional, (45)
"A magical home with access to all of the fun Salem has to offer, and most within walking distance! "
The price is AED 650
AED 2,335 total
includes taxes & fees
30 Mar - 31 Mar
The Warlock House: Bewitching - Speak Spells, Wave Wands, Ride Brooms - Walk to Salem, WiFi, Parking

Excellent 2 bedroom condo in South Boston

10.0 out of 10, Exceptional, (18)
"Fast communication with hosts, property was exactly as pictured and easy, flexible check in and out. Nice to unwind with large TV in family room! Was able to walk to the Convention Center. The parking is a challenge, we arrived after dark and being unfamiliar with the area it was difficult to find street parking nearby; however that may be expected for the area and I just didn’t realize! "
Excellent 2 bedroom condo in South Boston

Downtown Salem - Park & Play Modern 3 Bedroom

10.0 out of 10, Exceptional, (39)
"We were visiting family in the Salem area and this was perfect location for us to stay. We walked to many of our favorite Salem spots (Lulu’s, Harris’ comics) and had really good take out from the Babe right at the top of Ropes street. We really appreciated how bright and clean the apartment was, and how many clean towels were provided. Would love to stay again! "
The price is AED 580
AED 1,436 total
includes taxes & fees
30 Mar - 31 Mar
Downtown Salem - Park & Play Modern 3 Bedroom

🎖The Ashmont Suite - Close to Subway + Downtown🎖

10.0 out of 10, Exceptional, (39)
"Property was great and we hope to come again. Very cozy and clean. "
The price is AED 915
AED 1,769 total
includes taxes & fees
26 Mar - 27 Mar
🎖The Ashmont Suite - Close to Subway + Downtown🎖

LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo

9.6 out of 10, Exceptional, (156)
"Nice enough. Has Access to roof area. Good kitchen. Lots of choices to eat nearby "
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo

Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

10.0 out of 10, Exceptional, (3)
"Very nice and well situated haven close to historic Salem.Comfy and cosy with witchy theme well done!We had a great stay!"
The price is AED 1,286
AED 2,109 total
includes taxes & fees
13 Apr - 14 Apr
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

NEW! Boston Condo Near MBTA, 3Mi to Fenway! (U1)

9.0 out of 10, Wonderful, (6)
"Our stay at The Dean was nice for a group of 4. The property was clean and reasonably priced. It was a short distance in to the South side of Boston and parking in front of the property was not a problem. "
The price is AED 606
AED 1,322 total
includes taxes & fees
7 Apr - 8 Apr
NEW! Boston Condo Near MBTA, 3Mi to Fenway! (U1)

3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D

10.0 out of 10, Exceptional, (7)
"Spacious, clean, and well-equipped home, nice walks through the neighborhood and to nearby waterfront parks. Responsive and helpful hosts. Easy drive to local attractions as well as Boston and Cambridge. Would stay there again. "
3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D

*Vibrant Downtown 2BR|Salem+Beverly| Halloween

10.0 out of 10, Exceptional, (21)
"Kindest, most considerate hosts EVER. And the properties were lovelier than pictures. "
*Vibrant Downtown 2BR|Salem+Beverly| Halloween

Modern 2br with W/D in unit, Parking, central air

10.0 out of 10, Exceptional, (40)
"Very clean, and all amenities were provided. We felt very comfortable during our 3 night stay here. Would recommend!"
Modern 2br with W/D in unit, Parking, central air

Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry

The price is AED 500
AED 1,229 total
includes taxes & fees
25 Mar - 26 Mar
Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry

*Historic1710 2Br|Halloween Downtown+Parking

10.0 out of 10, Exceptional, (36)
"Gracious hosts. Charming property, comfortable home, great location. Walkable to the train station. Great food nearby. This was a stellar place to rent."
The price is AED 713
AED 1,482 total
includes taxes & fees
27 Mar - 28 Mar
*Historic1710 2Br|Halloween Downtown+Parking

Lg suite for up to 8 ppl/3 floor

9.4 out of 10, Exceptional, (12)
"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!"
The price is AED 257
AED 1,233 total
includes taxes & fees
30 Mar - 31 Mar
Lg suite for up to 8 ppl/3 floor

Spacious Marblehead Townhouse - Roof Deck with Panoramic Views

9.8 out of 10, Exceptional, (96)
"We thoroughly enjoyed this place. The only reason I gave a three on the description of the property is because in the initial description it says that there is a hot tub. There is only a Jacuzzi tub, but it actually looks like it lists both other than that this place was perfect."
Spacious Marblehead Townhouse - Roof Deck with Panoramic Views

Family-Friendly Salem Apt: Near Dtwn Sites!

10.0 out of 10, Exceptional, (19)
"The property was fantastic. I would definitely stay there again "
Family-Friendly Salem Apt: Near Dtwn Sites!

Modern Condo in Historic Marblehead, Walk everywhere, Parking, A/C, Deck & Grill

10.0 out of 10, Exceptional, (116)
"This was an excellent property that was such an easy place to stay out of the way. The location was perfect for our Salem getaway!"
Modern Condo in Historic Marblehead, Walk everywhere, Parking, A/C, Deck & Grill
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

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (448)
"Great location. Furniture was not that comfortable. A hot plate and larger fridge would be helpful. "
The price is AED 726
AED 841 total
includes taxes & fees
22 Apr - 23 Apr
Sonder 907 Main

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (172)
"We loved that the room was new and had everything we needed. Area was also great, close to shops, restaurants and bars. The only disappointment was not having a place to drop off our bags"
The price is AED 507
AED 942 total
includes taxes & fees
25 Mar - 26 Mar
Maverick Suites at 28 Fenway

Temple Place Suites

2.5 star property
6.8 out of 10, (191)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is AED 436
AED 704 total
includes taxes & fees
8 Apr - 9 Apr
Temple Place Suites
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?
Condos in Winchester range from AED 257 to AED 1,286 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 200 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?
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