Search Condo Rentals in Winchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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, (20)
"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, (43)
"Property was very clean and the location is in a great spot "
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

8.8 out of 10, Excellent, (3)
"Great location, away from hustle and bustle, but still just a few train stops away. Property is nice, clean and modern. "
The price is AED 500
AED 1,237 total
includes taxes & fees
12 May - 13 May
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, (12)
"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, (43)
"The Ashmont Suite was accurately described. It was in a quiet older neighborhood. The home was clean, well appointed and truly had every thing we needed. Communication from the owner was timely and clear. We stayed as a family as our son was running the Boston Marathon. The property was about a 20 minute Uber to the airport and downtown area. We thoroughly enjoyed our stay and would absolutely recommend it to others."
The price is AED 841
AED 1,685 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, (10)
"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
Convenient and Charming 2-bedroom condo with Private Parking, in South Boston
Living area

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

2.0 star property
5.6 out of 10, (9)
"What you see is what you get, but in a good way"
The price is AED 422
AED 916 total
includes taxes & fees
12 May - 13 May
Convenient and Charming 2-bedroom condo with Private Parking, in South Boston
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 AED 455
AED 931 total
includes taxes & fees
2 Jun - 3 Jun
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
*Historic1710 2Br Charm|Halloween Downtown+Parking
2 bedrooms, desk, iron/ironing board, travel crib

*Historic1710 2Br Charm|Halloween Downtown+Parking

10.0 out of 10, Exceptional, (41)
"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 Charm|Halloween Downtown+Parking
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Smart TV

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 AED 862
AED 1,570 total
includes taxes & fees
19 May - 20 May
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 AED 505
AED 1,297 total
includes taxes & fees
12 May - 13 May
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, (45)
"The house was very cute and spacious for my family trip. The location was great as well. "
The price is AED 735
AED 1,633 total
includes taxes & fees
12 May - 13 May
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

8.8 out of 10, Excellent, (13)
"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 AED 698
AED 1,811 total
includes taxes & fees
3 Jun - 4 Jun
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, (50)
"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 price is AED 1,348
AED 3,242 total
includes taxes & fees
12 May - 13 May
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, (146)
"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

9.4 out of 10, Exceptional, (3)
"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
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Lobby

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (474)
"The location was great. Close to the metro and good dining options. "
The price is AED 743
AED 862 total
includes taxes & fees
26 May - 27 May
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Global Luxury Suites Downtown Boston
Lobby lounge

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (550)
"Great place to stay, central and very secure"
The price is AED 835
AED 1,420 total
includes taxes & fees
22 May - 23 May
Global Luxury Suites Downtown Boston
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, (204)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is AED 485
AED 759 total
includes taxes & fees
12 May - 13 May
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 422 to AED 1,348 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.