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

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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 apartments

A residential house with a covered porch, a garage, and a well-maintained garden.

1. Charming 1-bedroom well located Garden Apartment in Historic West Medford

Charming 1-bedroom well located Garden Apartment in Historic West Medford
West Medford
10.0 out of 10, Exceptional, (16 reviews)
"Will not be disappointed!"
United States
Dave O.
$256 nightly
The price is $286
Nov 2 - Nov 3
Total with taxes and fees
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A wooden table with a sign that reads "Welcome, we're happy you're here" and a sign that says "The WiFi password is...".

2. 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, (25 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.
$348 nightly
The price is $389
Nov 8 - Nov 9
Total with taxes and fees
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

3. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (335 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$320 nightly
The price is $357
Oct 25 - Oct 26
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A bedroom with a bed, bedside table, chair, and a view of the kitchen.

4. Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!

Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!
Everett
9.4 out of 10, Exceptional, (20 reviews)
"We enjoyed our stay in Everett. Everything was clean and tidy when we arrived and the only small problem we had with a lock was quickly handled by the landlord. We enjoyed the area and tried several restaurants a quick walk away."
United States
Carolyn C.
$304 nightly
The price is $340
Oct 19 - Oct 20
Total with taxes and fees
Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

5. 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, (30 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
$387 nightly
The price is $433
Nov 8 - Nov 9
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A hallway with a welcome sign, a kitchen area with a counter and stools, and a patterned rug.

6. 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, (17 reviews)
"It was a great stay. The place was cosy and had everything you need and stuff you forgot to bring . I will definitely be staying here again."
United States
Jonathan
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
A modern kitchen with a large island, stainless steel appliances, and a minimalist design.

7. 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, (20 reviews)
"This place was great! Everything was very clean and new. It was easy to get in and out, and the host was extremely helpful and communicative. "
United States
Sierra K.
$414 nightly
The price is $462
Oct 29 - Oct 30
Total with taxes and fees
3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

8. Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#

Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
Cambridgeport
9.4 out of 10, Exceptional, (44 reviews)
"Very friendly and easy walk to fenway"
United States
thomas p.
$315 nightly
The price is $361
Nov 11 - Nov 12
Total with taxes and fees
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

9. Sleek Somerville Apartment near Encore!

Sleek Somerville Apartment near Encore!
East Somerville
9.6 out of 10, Exceptional, (20 reviews)
"Very clean. Perfect for what we needed."
Canada
Douglas A.
$477 nightly
The price is $533
Nov 4 - Nov 5
Total with taxes and fees
Sleek Somerville Apartment near Encore!
A modern bedroom with a large bed, a brick wall, and two black-and-white cityscape photographs.

10. Loft Condo Free Parking/MIT/Harvard/TD Garden

Loft Condo Free Parking/MIT/Harvard/TD Garden
Somerville
10.0 out of 10, Exceptional, (6 reviews)
"Very spacious, clean, and in a great location! The host was super easy to work with and made the check-in/out process easy!"
United States
AJ W.
$509 nightly
The price is $569
Oct 21 - Oct 22
Total with taxes and fees
Loft Condo Free Parking/MIT/Harvard/TD Garden
A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

11. Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.0 out of 10, Wonderful, (18 reviews)
"This is a convenient small apartment. However, it should be made clear that it is under the flight path to Logan airport. There were planes flying over till around 23:30, and they started again around 05:30. They were pretty loud."
United Kingdom
Philip
$199 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

12. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (446 reviews)
"Really pretty well maintained accomodation close to a lot of cool things to do in boston. its also pretty close to the train and bus station which was helpful to get around"
United States
Rakshitha
$234 nightly
The price is $269
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 28 Fenway
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

13. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (513 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
$162 nightly
The price is $186
Nov 5 - Nov 6
Total with taxes and fees
Temple Place Suites
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

14. The heart Cambridge/Boston Studio private yard free permit parking 1#

The heart Cambridge/Boston Studio private yard free permit parking 1#
Cambridgeport
9.4 out of 10, Exceptional, (93 reviews)
"Clean, comfy, cozy."
United States
Karen B.
$296 nightly
The price is $339
Nov 1 - Nov 2
Total with taxes and fees
The heart Cambridge/Boston Studio private yard free permit parking 1#
A hallway with brick walls and a polished floor, leading to a door.

15. Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.2 out of 10, Wonderful, (31 reviews)
"The place was great, and the host was even better! Very good communication and great customer service. I would highly recommend!"
United States
Travis
$223 nightly
The price is $245
Nov 2 - Nov 3
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

16. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (49 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
$306 nightly
The price is $352
Nov 9 - Nov 10
Total with taxes and fees
Bright 2BR by Boston Waterfront
A dining area with wooden chairs, a table with a patterned tablecloth, and potted plants.

17. 3 bedroom apartment next to T stop / off street parking

3 bedroom apartment next to T stop / off street parking
Charlestown
9.8 out of 10, Exceptional, (71 reviews)
"Excellent location. Host was very responsive. Easy check in. Property was clean and as advertised. Highly recommend."
United States
Teresa M.
$321 nightly
The price is $369
Nov 8 - Nov 9
Total with taxes and fees
3 bedroom apartment next to T stop / off street parking
A living room with a fireplace, a green sofa, a dining table with chairs, and a large window.

18. Cozy & Modern 1 BDR | Fenway within minutes!

Cozy & Modern 1 BDR | Fenway within minutes!
Fenway–Kenmore
8.4 out of 10, Very good, (5 reviews)
"The apt was spacious and comfortable.However, the amenities seemed very Spartan:very little in the way of cleaning supplies, thin cheap paper towels, thin toilet paper, extremely low wattage light bulbs made it hard to read, only one side table for the bed."
United States
Dean B.
$229 nightly
The price is $269
Nov 5 - Nov 6
Total with taxes and fees
Cozy & Modern 1 BDR | Fenway within minutes!
A spacious living room with a fireplace, a dining area with a glass table, and a kitchen visible in the background.

19. Lovely Fenway 1br | New to VRBO!

Lovely Fenway 1br | New to VRBO!
Fenway–Kenmore
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay here. The apartment is located close to many hospitals, shops and restaurants. There are parking spaces available for rent via Spothero directly behind the apartment, which is super convenient. The host was very responsive to all inquiries. I would gladly stay here again."
United States
Yesenia R.
$245 nightly
The price is $288
Nov 9 - Nov 10
Total with taxes and fees
Lovely Fenway 1br | New to VRBO!
A modern kitchen with dark cabinets, granite countertops, a stainless steel sink, and a microwave.

20. Serenity Suite Homes 2BD/1BA near Logan Intl/Metro

Serenity Suite Homes 2BD/1BA near Logan Intl/Metro
East Boston
9.6 out of 10, Exceptional, (8 reviews)
"Cute, comfortable apartment with easy access to downtown. Had everything we needed for our stay & the host was available if we needed anything."
United Kingdom
Amanda K.
$319 nightly
The price is $363
Nov 3 - Nov 4
Total with taxes and fees
Serenity Suite Homes 2BD/1BA near Logan Intl/Metro
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

Arcadian Hotel

Arcadian Hotel

8/10 Good
"Broken elevator made us carry bags down six flights to check out."
Steve 1-night trip
Posted 3 hours ago
Arcadian Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
664
Accommodation
1445 Apartments
Lowest Price
$186
Highest Price
$569

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 4130 hotels and accommodations including 1688 apartments. Discover some favorite places in the larger area like Fenway Park and Encore Boston Harbor.
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. Furnished Apartment Near Longwood: Located in Brookline, 7.3 mi/11.7 km away. Includes free WiFi. Access to onsite parking is available on site. Curated Designer Retreat • Pool • Gym • Dining: Located 5.9 mi/9.5 km away in Everett. A private pool, free WiFi, and separate dining areas are included. Access to a game room is available on site. Luxury Apartments by Hyatus at Boston Everett: Located in Everett, 6 mi/9.6 km from Winchester. Includes laundry facilities, free WiFi, and premium mattresses. Free parking and a fitness center are 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 Fenway Park and Encore Boston Harbor 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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