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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winchester condo rentals

Exterior detail

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!

Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
Beacon Hill
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay! Beautiful condo in a beautiful neighborhood that is walking distance to the commons."
United States
Grant T.
The price is AED 361
AED 1,007 total
includes taxes & fees
19 Jan - 20 Jan
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
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, (71 reviews)
"The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again."
United States
Pamela O.
The price is AED 239
AED 805 total
includes taxes & fees
20 Jan - 21 Jan
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
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, (52 reviews)
"Spacious condo, perfect location, and exceptional hospitality from mangers."
United States
Robert S.
The price is AED 542
AED 1,227 total
includes taxes & fees
18 Jan - 19 Jan
Bright & Spacious Loft Steps to the Freedom Trail
Fridge, microwave, oven, stovetop

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 reviews)
"Great stay"
United States
Alex c.
The price is AED 413
AED 1,331 total
includes taxes & fees
19 Jan - 20 Jan
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, (7 reviews)
"Beautiful place! Gorgeous historic home, great location. Has everything you could need and is very clean, tidy, and well maintained. Loved all the Halloween decorations, too! "
United States
Angela S.
The price is AED 588
AED 1,219 total
includes taxes & fees
30 Jan - 31 Jan
Spacious 3BR Salem Getaway, Modern & Walkable
Interior

Downtown Salem - Park & Play Modern 3 Bedroom

Downtown Salem - Park & Play Modern 3 Bedroom
Salem
10.0 out of 10, Exceptional, (58 reviews)
"This was a truly wonderful property - clean, generously stocked, perfect location and attentive owner"
United States
Valerie G.
The price is AED 463
AED 1,284 total
includes taxes & fees
17 Feb - 18 Feb
Downtown Salem - Park & Play Modern 3 Bedroom
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
10.0 out of 10, Exceptional, (3 reviews)
"Darling apartment - perfectly located close to shops and restaurants in downtown Marblehead. "
United States
Lauren P.
The price is AED 364
AED 866 total
includes taxes & fees
25 Jan - 26 Jan
Charming 1-bedroom condo in marvelous Marblehead with hidden patio
Smart TV

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston
stoneham
9.0 out of 10, Wonderful, (10 reviews)
"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.
The price is AED 613
AED 1,609 total
includes taxes & fees
25 Jan - 26 Jan
Modern Three Bedroom Condo - Near Boston
Dining

*1710 Historic 2BR |Downtown Salem Retreat|Parking

*1710 Historic 2BR |Downtown Salem Retreat|Parking
Downtown Salem
10.0 out of 10, Exceptional, (65 reviews)
"Great location, walking distance to anywhere we wanted to go. Would not hesitate to stay again! "
United States
Pat M.
*1710 Historic 2BR |Downtown Salem Retreat|Parking
Exterior

Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
2.0 star property
Swampscott
8.4 out of 10, Very Good, (6 reviews)
"Beautiful house & views,"
United States
Suzanne P.
The price is AED 729
AED 2,132 total
includes taxes & fees
18 Jan - 19 Jan
Coastal Charm: Lobster Châto
Smart TV, computer monitors

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, (30 reviews)
"Great location! Host was very attentive. Enjoyed our stay."
United States
Kim H.
The price is AED 500
AED 1,366 total
includes taxes & fees
18 Jan - 19 Jan
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
Smart TV, fireplace

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, (4 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is AED 477
AED 784 total
includes taxes & fees
26 Jan - 27 Jan
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
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
10.0 out of 10, Exceptional, (1 review)
"Very happy with our stay here! The place was clean, warm, and comfortable. I really appreciated the easy check in/out procedures. I loved that we weren’t expected to complete a long list of cleaning tasks before checking out. Crib, pack n play, and high chair were available which is awesome for traveling with a baby. "
United States
Amna S.
The price is AED 658
AED 1,523 total
includes taxes & fees
18 Jan - 19 Jan
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
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 reviews)
"It was a perfect location for our daily plans. The owner was very responsive to our needs "
United States
Mary P.
The price is AED 496
AED 1,714 total
includes taxes & fees
19 Jan - 20 Jan
Lg suite for up to 8 ppl/2 floor
Fridge, microwave, oven, stovetop

Modern 2-bedroom condo 1 mile to Salem

Modern 2-bedroom condo 1 mile to Salem
2.0 star property
Beverly
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay!! Excellent location with many walking distance food options. Super clean and super cozy!! Hosts were responsive and caring for our comfort while we stayed. Thank you for the snacks!!! We would definitely stay here again!!!"
United States
Melissa G.
The price is AED 1,010
AED 1,457 total
includes taxes & fees
26 Jan - 27 Jan
Modern 2-bedroom condo 1 mile to Salem
3 bedrooms, desk, iron/ironing board, free WiFi

Modern & Cozy 3-Bedroom Condo near Downtown

Modern & Cozy 3-Bedroom Condo near Downtown
Roxbury
10.0 out of 10, Exceptional, (8 reviews)
"One of the most cleanest places we’ve ever stayed!"
United States
Seetharaman S.
The price is AED 555
AED 1,436 total
includes taxes & fees
18 Jan - 19 Jan
Modern & Cozy 3-Bedroom Condo near Downtown
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
The price is AED 743
AED 1,610 total
includes taxes & fees
19 Jan - 20 Jan
Eastie Gem: Taste of local life by the waterfront, airport and train
Dining

Your cozy home away from home, close to subway and downtown Boston

Your cozy home away from home, close to subway and downtown Boston
Jamaica Plain
9.2 out of 10, Wonderful, (9 reviews)
"Great place ideally located."
Australia
Dennis M.
The price is AED 496
AED 1,360 total
includes taxes & fees
18 Jan - 19 Jan
Your cozy home away from home, close to subway and downtown Boston
Interior

Downtown Salem Chic - 3 Bedroom w/ Parking

Downtown Salem Chic - 3 Bedroom w/ Parking
Salem
10.0 out of 10, Exceptional, (5 reviews)
"Check in went very smooth and kitchen was well stocked with everything needed."
United States
Justin R.
Downtown Salem Chic - 3 Bedroom w/ Parking
Microwave, oven, stovetop, dishwasher

Adorable 1-bedroom apartment in welcoming Cambridge

Adorable 1-bedroom apartment in welcoming Cambridge
2.0 star property
North Cambridge
The price is AED 441
AED 883 total
includes taxes & fees
18 Jan - 19 Jan
Adorable 1-bedroom apartment in welcoming Cambridge
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

The Langham, Boston

The Langham, Boston

10/10 Excellent
"Amazing service and staff "
Inna 3-night trip
Posted 1 day ago
The Langham, Boston

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from AED 784 to AED 2,132 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 179 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.