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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winchester apartments

A stone house with a garden bed, a hose, and a brick pathway.

1. 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, (65 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.
$234 nightly
The price is $261
Sep 9 - Sep 10
Total with taxes and fees
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

2. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (457 reviews)
"The Property was comfortable, close to public transport, The Goston Common and lots of lively eateries."
United Kingdom
Lisa
$174 nightly
The price is $200
Sep 7 - Sep 8
Total with taxes and fees
Temple Place Suites
A row of brick townhouses with ornate architectural details, large windows, and a central staircase.

3. Stunning Back Bay Studio Apartment

Stunning Back Bay Studio Apartment
Back Bay
8.4 out of 10, Very Good, (13 reviews)
"Good use of space, comfortable bed and sofa, Very pleasant neighborhood walking distance to Fenway Park, Whole Foods and 2 subway stations. The kitchen is small but functional. The refrigerator either freezes salad or leaks water and the bathroom sink is tiny. But otherwise a sweet place to stay. Use Bounce if you need to stash your bags before check in or after check out."
United States
Donna L.
$195 nightly
The price is $229
Sep 7 - Sep 8
Total with taxes and fees
Stunning Back Bay Studio Apartment
A multi-story building with various storefronts, including 'ba&sh' and 'Ben Jerry's'.

4. Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
9.0 out of 10, Wonderful, (15 reviews)
"The communication with the host was very easy. Great location!"
Canada
Josee
$277 nightly
The price is $298
Sep 7 - Sep 8
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
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, (322 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$287 nightly
The price is $321
Sep 4 - Sep 5
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a white table and chairs.

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

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Wellington
10.0 out of 10, Exceptional, (18 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.
$324 nightly
The price is $362
Sep 7 - Sep 8
Total with taxes and fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
A living room with a fireplace, a dining table, a sofa, and large windows.

7. Charming 1 Bedroom | Newbury Street

Charming 1 Bedroom | Newbury Street
Back Bay
10.0 out of 10, Exceptional, (1 review)
"There are a few stairs to climb to get to the condo so just be prepared. It's in a great location. Easy to get to bars, shopping, restaurants etc."
United States
Lynette B.
$283 nightly
The price is $333
Sep 3 - Sep 4
Total with taxes and fees
Charming 1 Bedroom | Newbury Street
A hallway with a framed artwork of a person and a colorful bird illustration on the wall.

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

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Winthrop
9.8 out of 10, Exceptional, (12 reviews)
"Great location and wonderful hosts! Would definitely recommend to anyone staying in the Boston area. "
United States
Kristie P.
$198 nightly
The price is $221
Sep 17 - Sep 18
Total with taxes and fees
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.

9. Stellar South End Studio

Stellar South End Studio
Back Bay
9.0 out of 10, Wonderful, (4 reviews)
"This place is not fancy, but is clean and comfortable and exactly as advertised I had an issue with the WiFi and the host fixed it as soon as they could. I would definitely stay here again."
United States
Daniel
$245 nightly
The price is $288
Sep 20 - Sep 21
Total with taxes and fees
Stellar South End Studio
A living room with a sofa, a coffee table, a fireplace, and a TV mounted above it.

10. Wonderful Fenway 3br/2ba | Steps from Fenway Park!

Wonderful Fenway 3br/2ba | Steps from Fenway Park!
Fenway–Kenmore
10.0 out of 10, Exceptional, (4 reviews)
"Strong location and good spaces"
United States
Bryce G.
$348 nightly
The price is $409
Sep 7 - Sep 8
Total with taxes and fees
Wonderful Fenway 3br/2ba | Steps from Fenway Park!
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.

11. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (42 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
$298 nightly
The price is $343
Sep 8 - Sep 9
Total with taxes and fees
Bright 2BR by Boston Waterfront
A hallway with brick walls and a polished floor, leading to a door.

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

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.0 out of 10, Wonderful, (22 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
$227 nightly
The price is $249
Sep 9 - Sep 10
Total with taxes and fees
Enjoyable 2-bedroom lower level apartment in charming Lynn
A living room with a sofa, a glass coffee table, a TV mounted on the wall, a wooden floor, and a window with a view of trees.

13. 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.
$222 nightly
The price is $248
Sep 7 - Sep 8
Total with taxes and fees
NEW Modern Apartment Near Boston & Harvard Square.
A multi-story building with a curved facade, large windows, and a prominent billboard.

14. Big Bright Windows with great views of the city - Centrally located. Walk anywhere, MBTA nearby.

Big Bright Windows with great views of the city - Centrally located. Walk anywhere, MBTA nearby.
Downtown Boston
8.4 out of 10, Very Good, (10 reviews)
"Lovely clean apartment in a great area. It was with in walking distance to everything we wanted to see The host was fantastic- very responsive; accommodated all our requests. Highly recommend it! "
United States
Rimma Z.
$318 nightly
The price is $374
Sep 8 - Sep 9
Total with taxes and fees
Big Bright Windows with great views of the city - Centrally located. Walk anywhere, MBTA nearby.
A bedroom with a bed, bedside table, chair, and a view of the kitchen.

15. 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
9.6 out of 10, Exceptional, (19 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.
$285 nightly
The price is $319
Sep 21 - Sep 22
Total with taxes and fees
Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!
A modern bedroom with a large bed, a blue sofa, and a wooden dresser.

16. Modern North End Studio

Modern North End Studio
North End
9.4 out of 10, Exceptional, (20 reviews)
"Lovely flat in fantastic location."
United States
James
$357 nightly
The price is $410
Sep 6 - Sep 7
Total with taxes and fees
Modern North End Studio
A row of multi-story brick buildings with a central entrance, a flag, and parked cars on the street.

17. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (416 reviews)
"Great property beautiful vintage building great location"
United States
James
$282 nightly
The price is $324
Sep 11 - Sep 12
Total with taxes and fees
Maverick Suites at 28 Fenway
A modern kitchen with stainless steel appliances, a blue and white patterned sofa, and a cityscape painting on the wall.

18. Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (17 reviews)
"Great location- excellent place!"
United States
Deborah S.
$386 nightly
The price is $444
Sep 14 - Sep 15
Total with taxes and fees
Perfetto North End 1brm
A modern kitchen with wooden cabinets, a dining area with a table and chairs, and a sofa in the living area.

19. Bay Village Charming 1 Bedroom Apartment

Bay Village Charming 1 Bedroom Apartment
Bay Village
8.6 out of 10, Excellent, (7 reviews)
"Great location and easy to navigate from check in to check out. Would stay again "
United States
Jennifer K.
$273 nightly
The price is $321
Sep 7 - Sep 8
Total with taxes and fees
Bay Village Charming 1 Bedroom Apartment
A multi-story building with a classic architectural style, featuring a curved facade and numerous windows.

20. Downtown Boston - close to everything - Laundry in Building, Keyless Entry. Free Air Mattress too.

Downtown Boston - close to everything - Laundry in Building, Keyless Entry. Free Air Mattress too.
Downtown Boston
8.8 out of 10, Excellent, (3 reviews)
"Great location and super clean."
United States
Regan A.
$339 nightly
The price is $398
Sep 8 - Sep 9
Total with taxes and fees
Downtown Boston - close to everything - Laundry in Building, Keyless Entry. Free Air Mattress too.
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
"Great location, food and entertainment just outside the doors."
Stephen 2-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winchester

Winchester Apartments information

Number of reviews
19,624
Accommodation
1444 Apartments
Lowest Price
$112
Highest Price
$227

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 4246 hotels and accommodations including 1596 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. Curated Designer Retreat • Pool • Gym • Dining: Located in Everett, 5.9 mi/9.5 km away. Includes a private pool, free WiFi, and separate dining areas. Access to a game room is available on site. 3bdrm Apt next to Airport/Downtown 7 min drive: 7 mi/11.3 km away in Chelsea. Amenities include Smart TVs. Downtown Salem Retreat 2BD 3rd Floor: It's situated in Salem, 12.9 mi/20.8 km from Winchester.
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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