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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

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
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (140)
"This is a fantastic place. Quirky, clean and comfortable in an unbeatable location. The spiral stairs are steep and narrow so not for those with mobility issues. The plumbing does make noise but as Brits we all are used to old buildings with interesting sounds so no issue for us. We would definitely stay here again. Good clear instructions from owner."
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
Fridge, microwave, oven, stovetop

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
Living area

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 433
AED 933 total
includes taxes & fees
24 Mar - 25 Mar
Convenient and Charming 2-bedroom condo with Private Parking, in South Boston
🎖The Boiler Room - Close to Subway & Downtown🎖
Interior

🎖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 price is AED 364
AED 1,089 total
includes taxes & fees
23 Mar - 24 Mar
🎖The Boiler Room - Close to Subway & Downtown🎖
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, (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
Miscellaneous

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
Interior

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 635
AED 1,506 total
includes taxes & fees
30 Mar - 31 Mar
Downtown Salem - Park & Play Modern 3 Bedroom
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Fridge, microwave, oven, stovetop

🎖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
TV, DVD player, books, music library

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
Fridge, microwave, oven, stovetop

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)
Miscellaneous

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
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, (6)
"Boston was were we had picked to celebrate 3 birthdays. This location was great for walking to several breakfast locations and the train.Due to construction on main road made it a little harder to get to the grocery store. Overall some of the minor issues of the location we would rent here again. then catch"
3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D
*Stylish Downtown 2BR|Historic Salem+Beverly
Exterior

*Stylish Downtown 2BR|Historic Salem+Beverly

10.0 out of 10, Exceptional, (21)
"Kindest, most considerate hosts EVER. And the properties were lovelier than pictures. "
*Stylish Downtown 2BR|Historic Salem+Beverly
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, (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
Fridge, microwave, oven, stovetop

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

The price is AED 500
AED 1,208 total
includes taxes & fees
22 Mar - 23 Mar
Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry
*Historic1710 Halloween Gem| SalemDowntown+Parking
2 bedrooms, desk, iron/ironing board, travel crib

*Historic1710 Halloween Gem| SalemDowntown+Parking

10.0 out of 10, Exceptional, (36)
"Arrived a day early to see Salem. The location was perfect, walking distance to everything - including the wedding! The apartment is great and the hosts wonderful and responsive. Would book again."
The price is AED 713
AED 1,482 total
includes taxes & fees
27 Mar - 28 Mar
*Historic1710 Halloween Gem| SalemDowntown+Parking
Lg suite for up to 8 ppl/3 floor
Terrace/patio

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 290
AED 1,254 total
includes taxes & fees
24 Mar - 25 Mar
Lg suite for up to 8 ppl/3 floor
Spacious Marblehead Townhouse - Roof Deck with Panoramic Views
Interior

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!
Dining

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
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
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, (448)
"Great location. Furniture was not that comfortable. A hot plate and larger fridge would be helpful. "
The price is AED 762
AED 884 total
includes taxes & fees
22 Mar - 23 Mar
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, (170)
"The representative was very attentive and resourceful to a phone-in request to check-in a couple minutes early. He alleviated my concerns with his response and solutions. Excellent person! "
The price is AED 380
AED 796 total
includes taxes & fees
23 Mar - 24 Mar
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, (189)
"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 290 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?
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.