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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
Train to Boston! Cozy Apartment in Winchester
A residential house with a covered porch, a garage, and a well-maintained garden.

2. 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.
The price is CA $207
CA $402 total
includes taxes & fees
Oct 21 - Oct 22
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...".

3. 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.
The price is CA $250
CA $556 total
includes taxes & fees
Nov 8 - Nov 9
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.

4. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (333 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is CA $356
CA $508 total
includes taxes & fees
Oct 18 - Oct 19
Near Boston Historic two-bedroom with Modern Amenities
A bedroom with a bed, a ceiling fan, a painting on the wall, and a window with curtains.

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

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Wellington
10.0 out of 10, Exceptional, (21 reviews)
"It was the perfect location and amenities for our east coast vacation. Loved that everyone had their own room and television, the laundry access and accommodation, everything we needed in the kitchen and large space for everyone to watch a movie together. "
United States
J B.
The price is CA $292
CA $645 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
A bedroom with a bed, bedside table, chair, and a view of the kitchen.

6. 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.
The price is CA $250
CA $487 total
includes taxes & fees
Oct 29 - Oct 30
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.

7. 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.
The price is CA $183
CA $324 total
includes taxes & fees
Oct 14 - Oct 15
Newly refurbished, Sunny bright In-law suite.15 minute easy drive to Boston
A dining area with wooden chairs, a table with a patterned tablecloth, and potted plants.

8. 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.
The price is CA $248
CA $504 total
includes taxes & fees
Nov 8 - Nov 9
3 bedroom apartment next to T stop / off street parking
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.
The price is CA $238
CA $760 total
includes taxes & fees
Nov 4 - Nov 5
Sleek Somerville Apartment near Encore!
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

10. 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.
The price is CA $242
CA $484 total
includes taxes & fees
Oct 22 - Oct 23
Heart Cambridge free parking 1 bedroom MIT/Harvard/ Boston/4#
A brick building with a black front door, a staircase, and a well-maintained garden.

11. 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, (37 reviews)
"Friendly hosts"
United States
Jan
The price is CA $135
CA $310 total
includes taxes & fees
Oct 14 - Oct 15
Free Parking at 1 Bed Basement Apt, Near BU & MIT
A wooden building entrance with two lanterns, a paved path, and a tree with pink leaves in the background.

12. 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.
The price is CA $255
CA $482 total
includes taxes & fees
Nov 8 - Nov 9
The heart Cambridge/Boston Studio private yard free permit parking 1#
A hallway with a welcome sign, a kitchen area with a counter and stools, and a patterned rug.

13. 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
The price is CA $247
CA $434 total
includes taxes & fees
Oct 22 - Oct 23
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

14. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (438 reviews)
"Great price for the place given the location."
United States
Beenish
The price is CA $191
CA $358 total
includes taxes & fees
Nov 1 - Nov 2
Maverick Suites at 28 Fenway
A modern kitchen with dark cabinets, a white countertop, stainless steel appliances, and a central island with bar stools.

15. 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.
The price is CA $300
CA $746 total
includes taxes & fees
Nov 8 - Nov 9
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

16. 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
The price is CA $147
CA $321 total
includes taxes & fees
Nov 2 - Nov 3
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

17. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.8 out of 10, Excellent, (19 reviews)
"Cute place with a great location and responsive communication from the host. Would stay here again!"
United States
Lisa
The price is CA $133
CA $349 total
includes taxes & fees
Nov 4 - Nov 5
Stunning Back Bay Studio Apartment
A modern kitchen with a large island, stainless steel appliances, and a minimalist design.

18. 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.
The price is CA $230
CA $651 total
includes taxes & fees
Oct 29 - Oct 30
3BR2Bth Parking, Cambridge/Boston, W/D, Subway,A/C
A bedroom with a bed, a chair, a desk, a radiator, and a ceiling fan.

19. 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.
The price is CA $174
CA $461 total
includes taxes & fees
Oct 12 - Oct 13
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.

20. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (500 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
The price is CA $137
CA $247 total
includes taxes & fees
Nov 9 - Nov 10
Temple Place Suites
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 Revolution Hotel

The Revolution Hotel

10/10 Excellent
"Everything"
Ellen 1-night trip
Posted 1 hour ago
The Revolution Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
766
Accommodation
1445 Apartments
Lowest Price
CA $247
Highest Price
CA $760

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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