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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchester apartments

A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

1. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
3.0 star property
Winchester
10.0 out of 10, Exceptional, (1 review)
"Clean and spacious private entrance mother-in-law suite in a nice and quiet neighborhood. About a 25-40 minute ride, depending on traffic, into Boston."
United States
Selena
$241 nightly
The price is $270
Nov 17 - Nov 18
Total with taxes and fees
Train to Boston! Cozy Apartment in Winchester
A bedroom with a bed, desk, chair, dresser, and two bedside lamps.

2. Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Nice Appartement!Bus round the corner, very quiet!"
United States
Holger V.
$248 nightly
The price is $277
Nov 17 - Nov 18
Total with taxes and fees
Train to Boston! Cozy Apartment in Winchester
A residential house with a covered porch, a garage, and a well-maintained garden.

3. 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, (18 reviews)
"Great stay and great host! Would come back! Area is super safe and lovely!"
United States
I A.
$239 nightly
The price is $267
Nov 2 - Nov 3
Total with taxes and fees
Charming 1-bedroom well located Garden Apartment in Historic West Medford
A stone house with a garden bed, a hose, and a brick pathway.

4. 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, (68 reviews)
"Excellent place to stay in Medford. Everything was great and we ended up only had two persons staying here, for which it was great!"
United States
Michael C.
$273 nightly
The price is $305
Nov 3 - Nov 4
Total with taxes and fees
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
A spacious living room with a dining area, wooden columns, and a large window providing natural light.

5. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (337 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$266 nightly
The price is $297
Oct 26 - Oct 27
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A modern kitchen with white cabinets, stainless steel appliances, a tiled backsplash, and a window with blinds.

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

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Wellington
10.0 out of 10, Exceptional, (23 reviews)
"The property met y family’s needs."
United States
Charlie G.
$346 nightly
The price is $386
Oct 27 - Oct 28
Total with taxes and fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
A bedroom with a bed, bedside table, chair, and a view of the kitchen.

7. 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.
$291 nightly
The price is $326
Oct 29 - Oct 30
Total with taxes and fees
Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!
A bedroom with a large bed, a smaller bed, a nightstand with a lamp, a mirror, and a window with a view of greenery.

8. Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston

Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
Watertown
9.8 out of 10, Exceptional, (65 reviews)
"I was very satisfied with my stay at this property. Mehmet, our host, made sure that we had everything we needed to make our stay comfortable. If I returned to this area, I would definitely stay here again."
United States
Melissa F.
$212 nightly
The price is $237
Nov 8 - Nov 9
Total with taxes and fees
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A hallway with a welcome sign, a kitchen area with a counter and stools, and a patterned rug.

9. 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
$197 nightly
The price is $220
Nov 3 - Nov 4
Total with taxes and fees
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

10. 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, (31 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
$389 nightly
The price is $435
Nov 8 - Nov 9
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A modern outdoor seating area with a metal table and chairs, a potted plant, and a white sofa.

11. Eco-friendly Studio Close to Beach, Boston, Logan Airport & Train Station

Eco-friendly Studio Close to Beach, Boston, Logan Airport & Train Station
Revere
9.8 out of 10, Exceptional, (78 reviews)
"great place to stay"
United States
Emily M.
$160 nightly
The price is $179
Nov 4 - Nov 5
Total with taxes and fees
Eco-friendly Studio Close to Beach, Boston, Logan Airport & Train Station
A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

12. Sleek Somerville Apartment near Encore!

Sleek Somerville Apartment near Encore!
East Somerville
9.4 out of 10, Exceptional, (24 reviews)
"Very clean. Perfect for what we needed."
Canada
Douglas A.
$477 nightly
The price is $533
Oct 26 - Oct 27
Total with taxes and fees
Sleek Somerville Apartment near Encore!
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

13. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (460 reviews)
"Great price for the place given the location."
United States
Beenish
$212 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 28 Fenway
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.
$276 nightly
The price is $316
Nov 1 - Nov 2
Total with taxes and fees
The heart Cambridge/Boston Studio private yard free permit parking 1#
A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

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

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.2 out of 10, Wonderful, (21 reviews)
"Very amazing room to stay! Everything was very clean and comfortable! Host was very responsive and wonderful!"
United States
Edmund W.
$200 nightly
The price is $223
Nov 2 - Nov 3
Total with taxes and fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
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
9.6 out of 10, Exceptional, (50 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
$295 nightly
The price is $339
Nov 2 - Nov 3
Total with taxes and fees
Bright 2BR by Boston Waterfront
A bedroom with a bed, a chair, a desk, a radiator, and a ceiling fan.

17. Free Parking 2 Bed 1 Bath Steps from BU/Kenmore

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.6 out of 10, Excellent, (17 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
$283 nightly
The price is $324
Oct 28 - Oct 29
Total with taxes and fees
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

18. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (532 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
$144 nightly
The price is $165
Nov 25 - Nov 26
Total with taxes and fees
Temple Place Suites
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a large window providing natural light.

19. Beautiful 1BR near Fenway Park + Kenmore!

Beautiful 1BR near Fenway Park + Kenmore!
Fenway–Kenmore
9.0 out of 10, Wonderful, (2 reviews)
"Was an amazing stay!"
United States
mariia
$229 nightly
The price is $269
Nov 1 - Nov 2
Total with taxes and fees
Beautiful 1BR near Fenway Park + Kenmore!
A hallway with brick walls and a polished floor, leading to a door.

20. 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, (34 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
$207 nightly
The price is $227
Nov 2 - Nov 3
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
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

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Very friendly staffs, the room is clean. Great location only several minutes walk to everywhere; safe to walk early morning and late night."
Regina 5-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winchester

Winchester Apartments information

Number of reviews
1,733
Accommodation
1459 Apartments
Lowest Price
$165
Highest Price
$533

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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