Search Condo Rentals in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 170 Condo Rentals in Winchester with updated reviews, rates, and availability.

★Downtown Condo~Steps from the Water & Common★
Living Room

★Downtown Condo~Steps from the Water & Common★

10.0 out of 10, Exceptional, (43)
"Great place! We really enjoyed our stay here. Location is excellent, walking distance to Salem attractions and across the street from the water. Host was very helpful and communicative. Would happily stay here gain. "
The price is AED 441
AED 1,034 total
includes taxes & fees
19 Mar - 20 Mar
★Downtown Condo~Steps from the Water & Common★
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dining / Living Room

🎖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 694
AED 1,490 total
includes taxes & fees
20 Feb - 21 Feb
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Pet-friendly condo in lovely South Boston with WiFi, AC
Terrace/patio

Pet-friendly condo in lovely South Boston with WiFi, AC

Pet-friendly condo in lovely South Boston with WiFi, AC
Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!
Dining

Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!

2.0 star property
9.4 out of 10, Exceptional, (3)
"We had difficulty finding a place to host our family of (5) comfortably and had 2 bathrooms. This house was just that and more! We enjoyed being able to cook some of our meals in the fully stocked kitchen, even baked cookies, and relaxed and watched a movie in the Family Room. The location is outstanding, walking distance to a lot of places. The grocery store is only 3 minutes away walking! Tim was prompt to respond; answered all my questions and made the check-in process easy. Thanks Tim...
Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!
Modern 2br with W/D in unit, Parking, central air
Private kitchen

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

10.0 out of 10, Exceptional, (38)
"Property was very clean and the location is in a great spot "
Modern 2br with W/D in unit, Parking, central air
The Heart of Southie (Garage + Roof Deck)
Living area

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)
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Room

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥

10.0 out of 10, Exceptional, (54)
"We will continue to return to this location. Perfect for our trips to the area."
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
New Luxury Renovation | near T

New Luxury Renovation | near T

9.8 out of 10, Exceptional, (9)
"The unit was spotlessly clean. The location was good with the T line a short walk away. Communication was excellent. Overall, we were all very pleased with the accommodations. Would definitely recommend. "
New Luxury Renovation | near T
*Historic1710 Home| DowntownSalem +Parking

*Historic1710 Home| DowntownSalem +Parking

10.0 out of 10, Exceptional, (33)
"If you are looking for an incredible place to stay in Salem, here it is. Everything about our stay was top notch. Such a unique property with amazing owners. We will be back. "
*Historic1710 Home| DowntownSalem +Parking
Family-Friendly Salem Apt: Near Dtwn Sites!
Front Entrance and Driveway

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!
Bright Brownstone w Terrace+View
Private kitchen

Bright Brownstone w Terrace+View

2.0 star property
Bright Brownstone w Terrace+View
Historic Somerville Cambridge 1 Bed, Inman Square
Dining

Historic Somerville Cambridge 1 Bed, Inman Square

6.0 out of 10, (3)
"The property was okay, but not great. The check-in process was completely lacking, I called, emailed and texted every number I could find with no response until around 6 pm on check-in day. The basic supplies in the kitchen and bathroom were lacking or non-existent and the second 'bed', an air mattress leaked badly."
Historic Somerville Cambridge 1 Bed, Inman Square
Excellent 2 bedroom condo in South Boston
Private kitchen

Excellent 2 bedroom condo in South Boston

10.0 out of 10, Exceptional, (17)
"Convenient location close to the train station for access to downtown. Safe area, also close to park and beach. Unit was very clean and had everything needed. Dryer takes a little long but that's typical with all-in-one units. No designated parking if you have a car but was able to find close street parking."
Excellent 2 bedroom condo in South Boston
Right Near Convention Center and Train Station
Living Room

Right Near Convention Center and Train Station

4.0 star property
10.0 out of 10, Exceptional, (7)
"Overall, had a great stay in Boston! The hosts were friendly and were great with communication from the start. They were flexible with an early check-in which was a great added bonus. Kitchen and bathroom was stocked with everything we needed for the few days we were there. The unit was close to the restaurants and bars which made nightlife easier. Our favorite spot was Capo Restaurant. Would happily stay again! "
Right Near Convention Center and Train Station
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
Kitchen with granite counter tops and stainless steel appliances

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
Cute Boston Home | near T
Duplex 2: open concept living area

Cute Boston Home | near T

Cute Boston Home | near T
Lg suite for up to 8 ppl/2 floor
Catch your zzzzzz at this spacious bedroom with 45’ Plazma TV

Lg suite for up to 8 ppl/2 floor

9.8 out of 10, Exceptional, (7)
"This was the perfect place for us to stay on our girls’ trip. Super close to a T station and comfortably slept 4 people. "
The price is AED 253
AED 1,224 total
includes taxes & fees
24 Feb - 25 Feb
Lg suite for up to 8 ppl/2 floor
Direct ocean view 2 bed 2 bath walk to beach
Private kitchen

Direct ocean view 2 bed 2 bath walk to beach

7.6 out of 10, Good, (14)
"It was a good location for doing things south of Boston. Didn't know there was so many level steps up and down inside the house. Very minimal and basic. Need some cosmetic work. Over all good."
Direct ocean view 2 bed 2 bath walk to beach
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 481
AED 1,247 total
includes taxes & fees
19 Feb - 20 Feb
Downtown Salem - Park & Play Modern 3 Bedroom
Stunning South End/Back Bay Penthouse!
Outdoor dining

Stunning South End/Back Bay Penthouse!

10.0 out of 10, Exceptional, (83)
"We enjoyed the property. Beds were firm and comfortable, good location and we enjoyed the tbs and Disney plus for the kids. Hosts are great. "
Stunning South End/Back Bay Penthouse!
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

Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (432)
"The property was close to anything you could need and all processes were beyond easy. Having all access on your phone was amazing. "
The price is AED 472
AED 548 total
includes taxes & fees
18 Feb - 19 Feb
Sonder 907 Main
No. 284 powered by Sonder
Room

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (868)
"my favorite stay ever. i loved my stay and everything about it and can’t wait to come back soon. "
The price is AED 565
AED 667 total
includes taxes & fees
17 Feb - 18 Feb
No. 284 powered by Sonder
Temple Place Suites
Room

Temple Place Suites

2.5 star property
6.8 out of 10, (182)
"Insane lil spot for seeing Boston and surrounding areas!"
The price is AED 353
AED 607 total
includes taxes & fees
17 Feb - 18 Feb
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?
Prepare to pay from AED 253 to AED 694 per night for condos in Winchester. No matter your budget, you’ll find the perfect stay on Expedia. 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?
Pick from 170 condos in Winchester. No matter if you’re taking a trip with the family or getting away with your pals, Expedia can help you find the ideal base for your crew.
Why book your condo in Winchester with Expedia?
With Expedia, it’s a cinch to find your dream condo in Winchester. Looking for an upmarket stay? Try out our filters to search for properties that have a 5-star rating. If you’re sticking to a budget, choose how much you want to spend and then browse our fabulous deals. We’ll help you find the perfect stay whatever your getaway looks like.
How can I find cheap condos in Winchester?
Expedia can help you narrow your search for cheap condos in Winchester. To lock in your perfect stay in just a few clicks, simply use our handy filter tool to refine your search by amenities, star rating and budget.