A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchester condo rentals

A living room with a black leather sofa, a patterned armchair, and a colorful throw pillow. There are three windows with blinds, and the room has a high ceiling.

1. Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston
stoneham
8.8 out of 10, Excellent, (11 reviews)
"Enjoyed our stay; close to Stop & Shop, Target and freeway."
United States
Jeff J.
$492 nightly
The price is $518
Oct 22 - Oct 23
Total with taxes and fees
Modern Three Bedroom Condo - Near Boston
Private kitchen

2. Adorable 1-bedroom apartment in welcoming Cambridge

Adorable 1-bedroom apartment in welcoming Cambridge
North Cambridge
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay in Cambridge for the Boston marathon. Walking distance to the red line and busses made it very easy to get downtown. This place had everything you could think of to make it a comfortable stay, and the host had excellent communication. Would stay here again!"
United States
Peter C.
$294 nightly
The price is $336
Nov 1 - Nov 2
Total with taxes and fees
Adorable 1-bedroom apartment in welcoming Cambridge
A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with three black bar stools.

3. Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
Wakefield
9.6 out of 10, Exceptional, (10 reviews)
"Great stay"
United States
Alex c.
$416 nightly
The price is $465
Oct 19 - Oct 20
Total with taxes and fees
Stylish home next to train to Boston, near Salem
A living room with a sofa, a glass coffee table, and a staircase.

4. 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, (35 reviews)
"House was clean and comfortable, area had a convenient store nearby and local restaurants to eat. We had a great stay."
United States
Elizabeth
$400 nightly
The price is $446
Oct 27 - Oct 28
Total with taxes and fees
Spacious Modern Luxury Duplex Near Boston & Cambridge - Free Parking
A modern living room with a staircase, a sofa set, and a large window with curtains.

5. Delightful New England Townhome

Delightful New England Townhome
Woburn
6.0 out of 10, (1 review)
"It’s a very clean spot but feels old and few comforts like extra towels, hand towels or wash cloths were not available. There was no ice maker or trays to freeze ice. Parking was convenient host was helpful."
United States
Heather B.
$474 nightly
The price is $508
Oct 19 - Oct 20
Total with taxes and fees
Delightful New England Townhome
A modern living room with a sofa, coffee table, and a small table with books and a lamp. There is a kitchen area with cabinets, a refrigerator, and a microwave. A welcome sign is on the wall, and a basketball arcade game is visible.

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

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.6 out of 10, Excellent, (10 reviews)
"It was close to Boston and the airport"
United States
Lewis
$350 nightly
The price is $390
Nov 1 - Nov 2
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A bedroom with a bed, a window with curtains, a door, and wall-mounted artwork.

7. Union Square Hideaway · Steps to Green Line

Union Square Hideaway · Steps to Green Line
Winter Hill
$511 nightly
The price is $571
Oct 19 - Oct 20
Total with taxes and fees
Union Square Hideaway · Steps to Green Line
A residential house with a gray exterior, a white front door, and a small porch with steps. There are two trash bins outside the door.

8. Lovely Two Bedroom Condo in South Boston

Lovely Two Bedroom Condo in South Boston
South Boston
8.0 out of 10, Very good, (7 reviews)
"Place was everything it said it was. Clean and easy to get to. Parking with all the snow was difficult at times but if we are willing to walk a bit there are spaces. Coveneinet to restaurants and food"
United States
Dennis H.
$269 nightly
The price is $282
Oct 25 - Oct 26
Total with taxes and fees
Lovely Two Bedroom Condo in South Boston
A modern kitchen with a central island, wooden stools, and pendant lighting.

9. Spacious 4-bedroom 4-bath condo in Somerville with parking, outdoor lounge & AC

Spacious 4-bedroom 4-bath condo in Somerville with parking, outdoor lounge & AC
Somerville
$747 nightly
The price is $835
Oct 20 - Oct 21
Total with taxes and fees
Spacious 4-bedroom 4-bath condo in Somerville with parking, outdoor lounge & AC
A bedroom with a bed, bedside lamp, and a view of the outdoors through a door.

10. 3BR Hotel Alternative - Walk to Kendall Square

3BR Hotel Alternative - Walk to Kendall Square
Wellington-Harrington
$452 nightly
The price is $499
Nov 4 - Nov 5
Total with taxes and fees
3BR Hotel Alternative - Walk to Kendall Square
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, pendant lighting, and a view of the outdoors through a window.

11. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"Is a great place"
United States
Ramon G.
$490 nightly
The price is $563
Nov 4 - Nov 5
Total with taxes and fees
🎖The Ashmont Suite - Close to Subway + Downtown🎖
A brick building with a dark door, steps leading up to a porch, and potted plants on the ground floor.

12. 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
9.6 out of 10, Exceptional, (10 reviews)
"Great location!"
United States
Lea M.
$367 nightly
The price is $422
Nov 9 - Nov 10
Total with taxes and fees
Charming & Private 1-bedroom Condo in Historic Boston - next to MGH hospital!
A harbor with numerous boats and a prominent building with a clock tower in the background.

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

♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Marblehead Historic District
9.8 out of 10, Exceptional, (84 reviews)
"I honestly had my favorite stay of all time at this place. It was clean cozy and absolutely everything that we needed. I love the historical feel to it and it was perfection."
United States
Arianna
$270 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a glass table and chairs.

14. Modern & Stylish 1-Bedroom Condo near Downtown

Modern & Stylish 1-Bedroom Condo near Downtown
Roxbury
10.0 out of 10, Exceptional, (7 reviews)
"Location was great. Enjoy your stay."
United States
Gwendolyn M.
$332 nightly
The price is $382
Nov 2 - Nov 3
Total with taxes and fees
Modern & Stylish 1-Bedroom Condo near Downtown
A coastal house with a large balcony, a covered outdoor seating area, and a view of the beach.

15. Coastal Charm: Lobster Châto

Coastal Charm: Lobster Châto
Swampscott
8.8 out of 10, Excellent, (11 reviews)
"Beautiful house & views,"
United States
Suzanne P.
$523 nightly
The price is $557
Oct 19 - Oct 20
Total with taxes and fees
Coastal Charm: Lobster Châto
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

16. 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, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
$213 nightly
The price is $238
Nov 2 - Nov 3
Total with taxes and fees
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A modern living room with a sofa, TV, and a glass coffee table. There is a kitchen area with a bar and a dining table.

17. Bright & Spacious Loft Steps to the Freedom Trail

Bright & Spacious Loft Steps to the Freedom Trail
Downtown Boston
10.0 out of 10, Exceptional, (61 reviews)
"Trendy, clean room in great location"
United States
Rachel M.
$369 nightly
The price is $424
Nov 11 - Nov 12
Total with taxes and fees
Bright & Spacious Loft Steps to the Freedom Trail
A kitchen with a black refrigerator, white cabinets, a wooden table, and a window with patterned curtains.

18. Right Near Convention Center and Train Station

Right Near Convention Center and Train Station
South Boston
10.0 out of 10, Exceptional, (44 reviews)
"It was amazing Peter was fantastic. We would definitely stay here again."
United States
Kathy M.
$660 nightly
The price is $759
Oct 28 - Oct 29
Total with taxes and fees
Right Near Convention Center and Train Station
Living area

19. Back-Bay Upscale Central Condo Bos Common Downtown

Back-Bay Upscale Central Condo Bos Common Downtown
Bay Village
10.0 out of 10, Exceptional, (13 reviews)
"Great location. Very quiet yet close to everything. Had everything we needed."
United States
Christine H.
$849 nightly
The price is $974
Nov 10 - Nov 11
Total with taxes and fees
Back-Bay Upscale Central Condo Bos Common Downtown
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area set for six.

20. Lg suite for up to 8 ppl/3 floor

Lg suite for up to 8 ppl/3 floor
Dorchester
9.4 out of 10, Exceptional, (19 reviews)
"Property was secure and had a fantastic location.The owner was very friendly and gave so much great information about the area. Would absolutely book again!"
Canada
blake s.
$585 nightly
The price is $672
Nov 9 - Nov 10
Total with taxes and fees
Lg suite for up to 8 ppl/3 floor
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 Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Well maintained. Wish they had ac"
James 2-night trip
Posted 9 hours ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
388
Accommodation
169 Condo Rentals
Lowest Price
$238
Highest Price
$974

Frequently asked questions

How much do condos in Winchester cost?
Condos in Winchester range from $238 to $974 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 169 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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