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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 193 Condo Rentals in Winchester with updated reviews, rates, and availability.

The Heart of Southie (Garage + Roof Deck)
View from property

The Heart of Southie (Garage + Roof Deck)

10.0 out of 10, Exceptional, (19)
"This property was exactly what expected. Will book again next time we visit Boston."
The Heart of Southie (Garage + Roof Deck)
Modern 2br with W/D in unit, Parking, central air
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (42)
"Very very clean well stocked all the co Fort of home "
Modern 2br with W/D in unit, Parking, central air
🎖The Boiler Room - Close to Subway & Downtown🎖
Interior

🎖The Boiler Room - Close to Subway & Downtown🎖

9.8 out of 10, Exceptional, (68)
"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🎖
Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (2)
"Great location, away from hustle and bustle, but still just a few train stops away. Property is nice, clean and modern. "
The price is SAR 510
SAR 1,255 total
includes taxes & fees
28 Apr - 29 Apr
Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry
Right Near Convention Center and Train Station
Fridge, microwave, oven, stovetop

Right Near Convention Center and Train Station

4.0 star property
10.0 out of 10, Exceptional, (11)
"The apartment is nice and all you need is there. Good location."
Right Near Convention Center and Train Station
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Fridge, microwave, oven, stovetop

🎖The Ashmont Suite - Close to Subway + Downtown🎖

10.0 out of 10, Exceptional, (40)
"Great area, excellent property management and very clean "
The price is SAR 859
SAR 1,721 total
includes taxes & fees
13 May - 14 May
🎖The Ashmont Suite - Close to Subway + Downtown🎖
3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (8)
"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
Modern Condo in Historic Marblehead, Walk everywhere, Parking, A/C, Deck & Grill
Fridge, microwave, oven, stovetop

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
Excellent 2 bedroom condo in South Boston
Miscellaneous

Excellent 2 bedroom condo in South Boston

10.0 out of 10, Exceptional, (19)
"Exactly as advertised / nice place. Really close to the subway, so everything in Boston is accessible!!!"
Excellent 2 bedroom condo in South Boston
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
TV, DVD player, books, music library

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

9.6 out of 10, Exceptional, (159)
"Nice enough. Has Access to roof area. Good kitchen. Lots of choices to eat nearby "
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
Exterior

Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem

2.0 star property
8.6 out of 10, Excellent, (4)
"We just needed a night to stay between flights. Unit was spacious, 2 beds, and inflatable mattress that was super comfy. We all haad our own private "corner""
The price is SAR 409
SAR 884 total
includes taxes & fees
28 Apr - 29 Apr
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
*Historic1710 2Br|Halloween Downtown+Parking
2 bedrooms, desk, iron/ironing board, travel crib

*Historic1710 2Br|Halloween Downtown+Parking

10.0 out of 10, Exceptional, (40)
"Convenient location to downtown comfortable space for the six of us easy access great communication from the owners would definitely stay here again"
*Historic1710 2Br|Halloween Downtown+Parking
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Fridge, microwave, oven, stovetop

Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

10.0 out of 10, Exceptional, (4)
"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 SAR 619
SAR 1,270 total
includes taxes & fees
28 Apr - 29 Apr
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Le Elona – Private Guest Suite on a Scenic Estate
Terrace/patio

Le Elona – Private Guest Suite on a Scenic Estate

The price is SAR 516
SAR 1,325 total
includes taxes & fees
28 Apr - 29 Apr
Le Elona – Private Guest Suite on a Scenic Estate
Downtown Salem - Park & Play Modern 3 Bedroom
Interior

Downtown Salem - Park & Play Modern 3 Bedroom

10.0 out of 10, Exceptional, (42)
"The house was very cute and spacious for my family trip. The location was great as well. "
The price is SAR 690
SAR 1,592 total
includes taxes & fees
29 Apr - 30 Apr
Downtown Salem - Park & Play Modern 3 Bedroom
Lg Suite for up to 8 ppl/1 floor
Terrace/patio

Lg Suite for up to 8 ppl/1 floor

9.4 out of 10, Exceptional, (12)
"Great place! Plenty of room, clean, and well kept. Very close to a ton of stuff to see and do. Highly recommend!"
The price is SAR 469
SAR 1,531 total
includes taxes & fees
11 May - 12 May
Lg Suite for up to 8 ppl/1 floor
The Warlock House: Bewitching - Speak Spells, Wave Wands, Ride Brooms - Walk to Salem, WiFi, Parking
Beach

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

9.8 out of 10, Exceptional, (48)
"The warlock house is in walking distance to a lot of the places you would want to visit while in Salem. Check in was as simple as it gets, and they have great communication. And of course the rooms were themed so beautifully. The pictures don’t do it justice, it’s so much better in person. My kids loved the Alexa and all the spells. Will be booking again!!! "
The Warlock House: Bewitching - Speak Spells, Wave Wands, Ride Brooms - Walk to Salem, WiFi, Parking
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (143)
"The apartment was very clean and in an excellent location."
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
Stylish, Comfortable Luxury | Near T
Fridge, microwave, oven, stovetop

Stylish, Comfortable Luxury | Near T

9.0 out of 10, Wonderful, (2)
"Stayed here with three other adults for a weekend stay, enjoying Boston. The beds were comfortable, the kitchen was well equipped and the place was sunny and bright. "
Stylish, Comfortable Luxury | Near T
Boston Apartment | near T
Miscellaneous

Boston Apartment | near T

10.0 out of 10, Exceptional, (2)
"Nice, clean and had everything we needed. Great locations"
Boston Apartment | near T
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
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (466)
"The location was great. Close to the metro and good dining options. "
The price is SAR 710
SAR 824 total
includes taxes & fees
26 May - 27 May
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (189)
"Amazing stay, thank you!"
The price is SAR 383
SAR 806 total
includes taxes & fees
30 Apr - 1 May
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (198)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is SAR 495
SAR 776 total
includes taxes & fees
28 Apr - 29 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 SAR 409 to SAR 859 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 193 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.