Search and Rent Winchester Condos

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Feb 27 - Mar 1

Condo Rentals in Winchester

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

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

Marblehead
10.0 out of 10, Exceptional, (70)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
$217 nightly
The price is $242
Dec 2 - Dec 3
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Terrace/patio
Back-Bay Upscale Central Condo Bos Common Downtown

Back-Bay Upscale Central Condo Bos Common Downtown

Bay Village
10.0 out of 10, Exceptional, (8)
"Great location for this apartment. Check in was a breeze. Would definitely come back and stay here!"
United States
Sean M.
$735 nightly
The price is $843
Dec 3 - Dec 4
Total with taxes and fees
Back-Bay Upscale Central Condo Bos Common Downtown
Smart TV, books
Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail

Downtown Boston
10.0 out of 10, Exceptional, (51)
"Great location! My husband grew up outside Boston and commuted for college. At 75 he finally had the “ living in the city experience.” So close to the Common and T. We took advantage of the Senior Charlie Card and got around like locals. Shopping just outside our building! Highly recommend!"
United States
Cecilia T.
Bright & Spacious Loft Steps to the Freedom Trail
Exterior detail
Charming 1-bedroom condo in marvelous Marblehead with hidden patio

Charming 1-bedroom condo in marvelous Marblehead with hidden patio

2.0 star property
Marblehead
$159 nightly
The price is $177
Nov 11 - Nov 12
Total with taxes and fees
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Exterior
*Ghostly 2BR Halloween Home|Salem+Beverly|Parking

*Ghostly 2BR Halloween Home|Salem+Beverly|Parking

Beverly
10.0 out of 10, Exceptional, (31)
"Unique, clean property. Close to everything. Perfect for my sister and I while visiting our niece in Beverly. We loved it! "
United States
Paula S.
$286 nightly
The price is $319
Nov 23 - Nov 24
Total with taxes and fees
*Ghostly 2BR Halloween Home|Salem+Beverly|Parking
Fridge, microwave, oven, stovetop
Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

stoneham
8.8 out of 10, Excellent, (8)
"We enjoyed our stay and would definitely stay here again. It was clean, cute, very cute area, safe, and very short drive to Boston. We really loved the area and the people we interacted with were all so friendly! The beds were very comfy too!!"
United States
Meghan D.
$415 nightly
The price is $436
Nov 8 - Nov 9
Total with taxes and fees
Modern Three Bedroom Condo - Near Boston
Smart TV
Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem

2.0 star property
Wakefield
10.0 out of 10, Exceptional, (5)
"we were in Massachusetts for our youngest granddaughters college graduation. This place was great. Good location and great hosts! Beautiful neighborhood Easy to walk to breakfast, lunch or dinner. "
United States
Rebecca Z.
$383 nightly
The price is $428
Dec 8 - Dec 9
Total with taxes and fees
Stylish home next to train to Boston, near Salem
Fridge, microwave, oven, stovetop
Spacious 3BR Salem Getaway, Modern & Walkable

Spacious 3BR Salem Getaway, Modern & Walkable

Salem
10.0 out of 10, Exceptional, (6)
"The condo was what they said. 3 bedrooms, 2 full baths. Modern kitchen and nice living room. Nice neighborhood! For us this was perfect location. 1 parking space.Extremely clean!"
United States
Sheryl P.
Spacious 3BR Salem Getaway, Modern & Walkable
Outdoor dining
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Framingham
10.0 out of 10, Exceptional, (3)
"Everything was perfect! It was a wk detail stay and I would highly recommend it to anyone! Will come again! "
United States
Jessica L.
$191 nightly
The price is $213
Nov 8 - Nov 9
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Smart TV
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

Salem
9.8 out of 10, Exceptional, (8)
"Very nice and well situated haven close to historic Salem.Comfy and cosy with witchy theme well done!We had a great stay!"
Canada
Lucie S.
$347 nightly
The price is $387
Nov 18 - Nov 19
Total with taxes and fees
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Fridge, microwave, oven, stovetop
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking

Everett
10.0 out of 10, Exceptional, (29)
"Location from Boston commons was about 15 minutes (no traffic) The house was INCREDIBLY CLEAN! Our family of 5 (adult children) were comfortable and had plenty of space. We didn’t use the kitchen but again, it was spotless and inviting. I highly recommend this home and we travel A LOT!"
United States
kristen l.
$411 nightly
The price is $459
Nov 9 - Nov 10
Total with taxes and fees
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Dining
Lg suite for up to 8 ppl/2 floor

Lg suite for up to 8 ppl/2 floor

Dorchester
10.0 out of 10, Exceptional, (12)
"Very clean and spacious flat. Plenty of room for the family. I was concerned about parking but was able to find a spot to park close by and easily over the weekend. Would recommend! "
United States
Tiffany W.
$406 nightly
The price is $467
Nov 10 - Nov 11
Total with taxes and fees
Lg suite for up to 8 ppl/2 floor
Interior
Modern & Stylish 1-Bedroom Condo near Downtown

Modern & Stylish 1-Bedroom Condo near Downtown

Roxbury
10.0 out of 10, Exceptional, (5)
"I had a great stay at Daniel’s place. The apartment was exactly as described—clean, and comfortable. It had everything I needed, and the bed was especiallyf comfortable after long days out. The location made it easy to get around, short ride uber to most shops, restaurants, and public transit close by.Daniel was a responsive and thoughtful host. He checked in to make sure everything was going well and responded quickly when I had a question. I appreciated how easy the whole process was, from...
United States
Jhonatan A.
$344 nightly
The price is $396
Nov 10 - Nov 11
Total with taxes and fees
Modern & Stylish 1-Bedroom Condo near Downtown
TV, fireplace
Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto

2.0 star property
Swampscott
8.8 out of 10, Excellent, (5)
"I was quite disappointed with my recent stay. The hot tub was not as advertised; it was empty, not able to be used and the cleanliness left much to be desired. I also experienced issues with the Wi-Fi connection, making it difficult to stay connected for work. Additionally, the bed broke nearly caused an injury to my family. Overall, I expected a more comfortable and smooth experience given the price. Unfortunately, I left feeling unsatisfied. "
United States
Jessica G.
$564 nightly
The price is $604
Nov 11 - Nov 12
Total with taxes and fees
Coastal Charm: Lobster Châto
Interior
Downtown Salem - Park & Play Modern 3 Bedroom

Downtown Salem - Park & Play Modern 3 Bedroom

Salem
10.0 out of 10, Exceptional, (57)
"Loved this place!! We all had our own room and everything was so clean and organized!! They had everything you could need. We will definitely be staying again in the future and have already recommended to everyone we know! Plus, it’s within walking distance to everything. Highly recommend this place!! "
United States
Britney W.
$439 nightly
The price is $490
Nov 10 - Nov 11
Total with taxes and fees
Downtown Salem - Park & Play Modern 3 Bedroom
Interior
Downtown Salem Chic - 3 Bedroom w/ Parking

Downtown Salem Chic - 3 Bedroom w/ Parking

Salem
10.0 out of 10, Exceptional, (4)
"Check in went very smooth and kitchen was well stocked with everything needed."
United States
Justin R.
$409 nightly
The price is $457
Nov 11 - Nov 12
Total with taxes and fees
Downtown Salem Chic - 3 Bedroom w/ Parking
Fridge, microwave, oven, stovetop
Eastie Gem: Taste of local life by the waterfront, airport and train

Eastie Gem: Taste of local life by the waterfront, airport and train

2.0 star property
East Boston
$381 nightly
The price is $438
Nov 10 - Nov 11
Total with taxes and fees
Eastie Gem: Taste of local life by the waterfront, airport and train
Smart TV, computer monitors, printers
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Chelsea
$332 nightly
The price is $371
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Exterior detail
Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston

South Boston
7.8 out of 10, Good, (6)
"We have stayed in a lot of VRBOs and this is one I would not return to. The location wasn’t near really anything, it smelled funny when we arrived, no washer and dryer and not enough towels to get us through the stay, the parking on the street was never open, we parked in the wrong spot- nothing was marked and we almost got towed. My kids woke up to spiders crawling across them. We actually Moved out a day early because of this. Going back and reading the reviews on this property I can now see...
United States
Katheryn S.
$503 nightly
The price is $547
Nov 8 - Nov 9
Total with taxes and fees
Lovely Two Bedroom Condo in South Boston
Beach
*Spacious Spooky 3BR Home|Salem+Beverly|Parking

*Spacious Spooky 3BR Home|Salem+Beverly|Parking

Beverly
10.0 out of 10, Exceptional, (19)
"Very clean, everything we needed. Very nice place, highly recommend it."
United States
Peggy S.
$340 nightly
The price is $380
Nov 16 - Nov 17
Total with taxes and fees
*Spacious Spooky 3BR Home|Salem+Beverly|Parking
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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Top Winchester Hotel Reviews

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

10/10 Excellent
"The service was great "
Damon 1-night trip
Posted 17 hours ago
Copley Square Hotel, a FOUND Hotel

Find out more about Winchester

Winchester Condo Rentals information

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Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from to 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 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.
What is there to do in Winchester near my condo?
The most useful travel accessory is a well-planned itinerary. Winter Pond is a terrific place to kick-start your adventures in Winchester.

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