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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

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, (18)
"We had the pleasure of staying at this perfect VRBO for 3 days. The unit is exactly as it is displayed in the photo’s but it is so much more. Everything you need is on site and the garage and roof top space are wonderful additions. The hosts are wonderful at communicating and are prompt in responding, day or night. There is a little corner store just a few steps away in case you need cheese and crackers or a sweet treat. We spent a lot of time in Boston site seeing and it was easy to...
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, (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
🎖The Boiler Room - Close to Subway & Downtown🎖
Interior

🎖The Boiler Room - Close to Subway & Downtown🎖

9.8 out of 10, Exceptional, (68)
"I enjoyed staying at this property. It was cozy, well-decorated, and homey, which made me feel very comfortable. I appreciated that it was clean and well-appointed. My only two notes are that the refrigerator is not very large so it was difficult to keep my leftovers. Also, I enjoyed the location, which sage, but will note for others that it is a bit far from central Boston. The host, Eddie, was very communicative, helpful, and responsive. I would stay here again. "
🎖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)
"The apartment is beautiful spacious, minimalist in furniture juhowever all you need"
The price is AED 500
AED 1,216 total
includes taxes & fees
16 Apr - 17 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, (9)
"We recently stayed at Peter's Boston apartment for our kid's spring break. We were there looking at colleges and exploring such an amazing city. The apartment was in a fantastic location. We were just a few minute walk to the Red line and could be all over the city with no hassle. We could also walk to neighborhood restaurants with ease. The apartment was very clean and just perfect for our family of 4. Peter was an amazing host and very responsive to all of my questions. He also provided...
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)
"Super clean and nice location, just a short walk to the T"
The price is AED 951
AED 1,811 total
includes taxes & fees
25 Apr - 26 Apr
🎖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
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)
"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 426
AED 920 total
includes taxes & fees
15 Apr - 16 Apr
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, (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
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, (157)
"All four adults loved the place! Reasonable location and rate for exploring Boston. Very comfortable, safe, and room for all of us--including our car. Even had a TV for late night March Madness! A must for at least one of us! :) Though we never met Gary, he was the perfect host--very informative and staying in contact before, during, and after! Just a reminder for those with physical limitations--it is three flights up."
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 400
AED 866 total
includes taxes & fees
17 Apr - 18 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)
"We had a wonderful time in Salem! The house was lovely and the location was perfect. Everything we wanted to do was within an easy walking distance. We would absolutely stay here again!"
The price is AED 889
AED 1,713 total
includes taxes & fees
20 Apr - 21 Apr
*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 AED 661
AED 1,313 total
includes taxes & fees
29 Apr - 30 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 AED 505
AED 1,297 total
includes taxes & fees
15 Apr - 16 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 AED 580
AED 1,436 total
includes taxes & fees
15 Apr - 16 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)
"I stayed with friends to visit the JFK library an other points of interest. The location was perfect for the library. The subway line is close by so one can use that to go into the city. Nice restaurants and food markets are close by. Parking is difficult but doable.apartment has everything one needs yo stay. "
The price is AED 588
AED 1,664 total
includes taxes & fees
7 May - 8 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, (45)
"A magical home with access to all of the fun Salem has to offer, and most within walking distance! "
The price is AED 713
AED 2,414 total
includes taxes & fees
18 Apr - 19 Apr
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, (142)
"Great location for a weekend trip to visit my son"
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
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, (456)
"Fair price, good environment."
The price is AED 768
AED 891 total
includes taxes & fees
22 Apr - 23 Apr
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, (182)
"Clean, as pictured, updated. "
The price is AED 375
AED 790 total
includes taxes & fees
22 Apr - 23 Apr
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, (196)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is AED 436
AED 704 total
includes taxes & fees
27 Apr - 28 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 400 to AED 951 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.
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.