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

Apartments in Winchester for Rent

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winchester apartments

Property grounds

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Medford
10.0 out of 10, Exceptional, (61 reviews)
"Owner accessible, and cleanliness and convenience was very good."
United States
Ian
$235 nightly
The price is $262
Aug 12 - Aug 13
Total with taxes and fees
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Dining

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
Medford Hillside
9.4 out of 10, Exceptional, (24 reviews)
"The quiet side street in Medford was great after spending our days in Boston. The close proximity to public transportation was also a plus. No worries about city parking at all.The house was super clean and cozy just as advertised!"
United States
Marla M.
$345 nightly
The price is $385
Jul 29 - Jul 30
Total with taxes and fees
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
Coffee/tea maker, fridge, microwave, oven

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Wellington
10.0 out of 10, Exceptional, (13 reviews)
"Convenient location, place was super comfy and well furnished. Thank you! "
United States
Amanda K.
$418 nightly
The price is $467
Aug 16 - Aug 17
Total with taxes and fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.0 out of 10, Good, (421 reviews)
"Great location so close to everything"
United States
Hunter
$170 nightly
The price is $195
Jul 29 - Jul 30
Total with taxes and fees
Temple Place Suites
Exterior

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.6 out of 10, Excellent, (27 reviews)
"Friendly hosts"
United States
Jan
$198 nightly
The price is $216
Jul 29 - Jul 30
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (396 reviews)
"Beautiful building, the staircase is really fantastic. I love having a private bathroom and a mini fridge. Amazing place, especially for the price I got it at. I bet all the units are really nice too. Definitely will be booking this place for my future trips."
United States
Amy
$211 nightly
The price is $243
Jul 28 - Jul 29
Total with taxes and fees
Maverick Suites at 28 Fenway
Living area

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (49 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$272 nightly
The price is $311
Aug 6 - Aug 7
Total with taxes and fees
On River/Harvard Sq. two blocks
2 bedrooms, WiFi, bed sheets

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.6 out of 10, Excellent, (38 reviews)
"Perfect location to explore Cambridge."
United States
Anonymous traveler
$280 nightly
The price is $321
Aug 9 - Aug 10
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.6 out of 10, Excellent, (8 reviews)
"Would stay again"
United States
mark p.
$200 nightly
The price is $235
Jul 29 - Jul 30
Total with taxes and fees
Studio Awaits Your Next Stay!
Interior

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Billerica
10.0 out of 10, Exceptional, (14 reviews)
"Great comfortable themed place. Clean, tons of amenities. Quiet area. A joy to stay at"
United States
Elizabeth E.
$186 nightly
The price is $208
Jul 30 - Jul 31
Total with taxes and fees
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Interior

Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (315 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$316 nightly
The price is $353
Aug 2 - Aug 3
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
2 bedrooms, desk, iron/ironing board, WiFi

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.4 out of 10, Very Good, (6 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
$281 nightly
The price is $322
Aug 2 - Aug 3
Total with taxes and fees
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Coffee/tea maker, fridge, microwave, oven

3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces

3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
East Somerville
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
$384 nightly
The price is $429
Aug 2 - Aug 3
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
2 bedrooms, desk, WiFi

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Fenway–Kenmore
10.0 out of 10, Exceptional, (5 reviews)
$409 nightly
The price is $528
Aug 20 - Aug 21
Total with taxes and fees
Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
TV, offices

Studio in the Heart of Boston!

Studio in the Heart of Boston!
Downtown Boston
10.0 out of 10, Exceptional, (2 reviews)
"My stay was excellent! One of the best parts was how responsive the property management team was to communicate with me so quickly on the VRBO app."
United States
Landon W.
$244 nightly
The price is $287
Aug 20 - Aug 21
Total with taxes and fees
Studio in the Heart of Boston!
TV

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (27 reviews)
"Excellent location, wonderful unit! "
United States
Mary M.
$385 nightly
The price is $443
Jul 30 - Jul 31
Total with taxes and fees
Prime Central 1brm in North End Boston
1 bedroom, desk, iron/ironing board, internet

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (14 reviews)
"All good, would definitely stay again"
United States
Dan C.
$231 nightly
The price is $272
Jul 29 - Jul 30
Total with taxes and fees
Cozy Studio Steps from Boston Common and Theaters
Smart TV

NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (52 reviews)
"That was the most comfortable bed I have slept in away from home!"
United States
Kimberly M.
$272 nightly
The price is $304
Aug 3 - Aug 4
Total with taxes and fees
NEW Modern Apartment Near Boston & Harvard Square.
Smart TV, books

Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (37 reviews)
"Great location and responsive host! Had everything we needed"
United States
Abbey H.
$276 nightly
The price is $318
Jul 29 - Jul 30
Total with taxes and fees
Bright 2BR by Boston Waterfront
Coffee/tea maker, fridge, microwave, oven

3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C

3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
Ward Two
9.6 out of 10, Exceptional, (19 reviews)
"The host was extremely helpful and communicative. Place was exceptionally clean as well. Kind of small for more than 4 people, but for smaller groups this is a fantastic stay!"
United States
Sean B.
$506 nightly
The price is $565
Aug 19 - Aug 20
Total with taxes and fees
3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
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
"."
Alvaro 7-night trip
Posted less than an hour ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Winchester

Winchester Apartments information

Number of reviews
1,445
Accommodation
1446 Apartments
Lowest Price
$195
Highest Price
$565

Frequently asked questions

What's it like to stay at an apartment in Winchester?
There are plenty of places to stay with in the Boston area, with 4249 hotels and accommodations including 1541 apartments. Discover some favorite places in the larger area like TD Garden and Fenway Park.
Why choose apartments instead of traditional hotels?
Often more spacious than a traditional hotel room, an apartment includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for couples looking for something with a more local feel.
What's the best apartment I should consider for a stay in Winchester?
Listed below are some of the more popular apartments in the area: Temple Place Suites: Located in Boston, 7.7 mi/12.4 km from the heart of Winchester. Includes free WiFi. Access to onsite laundry facilities is available on site. Maverick Suites at 28 Fenway: Located 7.7 mi/12.5 km away in Boston. Free WiFi and Smart TVs are included. Onsite laundry facilities and concierge services are on site. Enjoyable 2-bedroom lower level apartment in charming Lynn: It's situated in Lynn, 10 mi/16 km away. Includes free WiFi and Smart TVs. Salem Haunted Happenings Retreat: 13.7 mi/22 km away in Salem. Lovely 1.5 bedroom in the great historic town: Located in Salem, 13.2 mi/21.3 km from Winchester. Includes free WiFi, fireplaces, and Smart TVs. Access to onsite laundry facilities is available on site.
What can I expect from the weather in Winchester?
Though weather is just one factor, it can really affect your travel plans, especially when you're planning an extended stay in Winchester. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What should I see and do in Winchester?
Explore the area and family-friendly sights such as Winter Pond, or get out into nature at a spot like Boston Common. You'll find favorite places to visit like TD Garden and Fenway Park in the larger area.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) away from the city center. Otherwise, look for flights into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away. To explore the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station.

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