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Compare 171 Condo Rentals in Winchester with updated reviews, rates, and availability.

Light-filled condo near airport and city with AC, W/D, patio, balcony, & hot tub

Light-filled condo near airport and city with AC, W/D, patio, balcony, & hot tub

10.0 out of 10, Exceptional, (1)
"Beautiful modern updated condo. Located in such a cute and quiet neighborhood! Highly recommend "
Light-filled condo near airport and city with AC, W/D, patio, balcony, & hot tub
★Downtown Condo~Steps from the Water & Common★
Living Room

★Downtown Condo~Steps from the Water & Common★

10.0 out of 10, Exceptional, (40)
"We booked this trip to check off a long time bucket list to explore the history of the witch trials. This property was perfect for us. Clean and within walking distance to all the district has to offer. Thank you so much!"
★Downtown Condo~Steps from the Water & Common★
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!
♥ 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, (52)
"We found the vrbo was perfect for walking or driving to various local interests and restaraunts. We appreciated the coziness of the apartment. Great spot for a get away!!"
The price is AED 297
AED 881 total
includes taxes & fees
7 Jan - 8 January 2025
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dining / Living Room

🎖The Ashmont Suite - Close to Subway + Downtown🎖

10.0 out of 10, Exceptional, (37)
"Apartment was stunning. Like home from home. Location suited us as we had a car. "
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Stunning South End/Back Bay Penthouse!
Outdoor dining

Stunning South End/Back Bay Penthouse!

10.0 out of 10, Exceptional, (80)
"I Love this place. It is all about the privacy & the VIEWS! Both bedrooms have bay windows with city views, but the 2nd floor of this penthouse is a roof top refuge. Dinning alfresco is expected, & at night the Boston Skyline was our own private light show! Sue & David,(the Host's) were so accommodating, before I arrived, to the day I left. What I really loved was how they took an 1800yr old Brownstone left the history and character, but modernized it for comfort. Fantastic location walk to...
Stunning South End/Back Bay Penthouse!
Spacious Marblehead Townhouse - Roof Deck with Panoramic Views
Living area

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
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
Rehabbed 3BR2Bth, parking, Cambridge/Boston
Private kitchen

Rehabbed 3BR2Bth, parking, Cambridge/Boston

2.0 star property
9.6 out of 10, Exceptional, (7)
"Beautiful place, Target store and other stores are next door. Responsive host, clean apartment. Lovely view. Be ready for the steep climb up and down the stairs, especially if you are given the third floor. I’ll definitely book this again. "
The price is AED 698
AED 1,772 total
includes taxes & fees
23 Dec - 24 Dec
Rehabbed 3BR2Bth, parking, Cambridge/Boston
Historic home with a full kitchen - right in the heart of Salem

Historic home with a full kitchen - right in the heart of Salem

2.0 star property
Historic home with a full kitchen - right in the heart of Salem
Beautiful 2-bedroom with parking close to Cambridge/Watertown line
Property grounds

Beautiful 2-bedroom with parking close to Cambridge/Watertown line

2.0 star property
Beautiful 2-bedroom with parking close to Cambridge/Watertown line
The Warlock House: Bewitching - Speak Spells, Wave Wands, Ride Brooms - Walk to Salem, WiFi, Parking
Lighting magic at the Warlock House - let's go to a Haunted House

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

9.8 out of 10, Exceptional, (37)
"We loved the Warlock house! It’s just as fun as the pictures and description make it look. The decor and lighting sets such a cool atmosphere. Great location for walking to most everything to do in Salem. Beds are comfy, and everything you could need in the kitchen. Would definitely recommend!!"
The Warlock House: Bewitching - Speak Spells, Wave Wands, Ride Brooms - Walk to Salem, WiFi, Parking
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
Front of Building

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
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, (37)
"Nice property. Very clean"
Modern 2br with W/D in unit, Parking, central air
Contemporary Farmhouse-Style Retreat | near T

Contemporary Farmhouse-Style Retreat | near T

9.6 out of 10, Exceptional, (9)
"Apartment was perfect for our needs. Great condition, beautifully decorated and equipped. Lack of nearby amenities in the neighborhood was the only downside, but we felt that was reflected in the price, and there were a few cafes nearby."
Contemporary Farmhouse-Style Retreat | near T
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
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
Sweet Retreat
Exterior

Sweet Retreat

3.0 star property
10.0 out of 10, Exceptional, (3)
"Great place for a family, we had our 18yr niece with us so having a separate bedroom for her was a great find. Marblehead was an ideal location for getting around. Easy drives getting to Boston, Salem, Concord, Gloucester and the beaches packed in a lot in seven days"
Sweet Retreat
Downtown Salem - Park & Play Modern 3 Bedroom
Interior

Downtown Salem - Park & Play Modern 3 Bedroom

10.0 out of 10, Exceptional, (38)
"This place is great. It's exactly like the photos, in a safe place, walkable to downtown. It's also very clean. I have pretty bad dust allergies, to the point of bringing my own pillows to hotels, but didn't have a problem here."
The price is AED 867
AED 1,740 total
includes taxes & fees
23 Dec - 24 Dec
Downtown Salem - Park & Play Modern 3 Bedroom
Modern Three Bedroom Condo - Near Boston
Livingroom

Modern Three Bedroom Condo - Near Boston

8.6 out of 10, Excellent, (4)
"My family and I really enjoyed our stay here. It was clean and had games to play if that's your sort of thing. Located right off of Main Street, Stoneham so made getting around super easy. Restaurants and convenience store within walking distance. The host was super attentive and always responded quickly to our questions. Would surely recommend to others."
The price is AED 659
AED 1,649 total
includes taxes & fees
23 Dec - 24 Dec
Modern Three Bedroom Condo - Near Boston
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

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Private kitchen

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

7.4 out of 10, Good, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (405)
"Perfect location!"
The price is AED 472
AED 548 total
includes taxes & fees
23 Dec - 24 Dec
Sonder 907 Main
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is AED 367
AED 781 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
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 297 to AED 867 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 171 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.