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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester apartments

Property grounds

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, (64 reviews)
"Excellent communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
$238 nightly
The price is $265
Aug 16 - Aug 17
Total with taxes and fees
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
Coffee/tea maker, fridge, microwave, oven

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

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Wellington
10.0 out of 10, Exceptional, (15 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.
$358 nightly
The price is $400
Aug 16 - Aug 17
Total with taxes and fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Exterior

3. 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, (32 reviews)
"Friendly hosts"
United States
Jan
$199 nightly
The price is $217
Aug 17 - Aug 18
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
2 bedrooms, WiFi, bed sheets

4. Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.6 out of 10, Excellent, (39 reviews)
"Perfect location to explore Cambridge."
United States
Anonymous traveler
$280 nightly
The price is $321
Aug 18 - Aug 19
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks
Coffee/tea maker, fridge, microwave, oven

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, (28 reviews)
"Beautiful unit with attentive host and safe parking. We enjoyed our stay."
United States
Debbie L.
$365 nightly
The price is $407
Aug 16 - Aug 17
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

6. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (438 reviews)
"Great location so close to everything"
United States
Hunter
$174 nightly
The price is $200
Aug 19 - Aug 20
Total with taxes and fees
Temple Place Suites
Interior

7. 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, (15 reviews)
"Great comfortable themed place. Clean, tons of amenities. Quiet area. A joy to stay at"
United States
Elizabeth E.
$229 nightly
The price is $255
Sep 7 - Sep 8
Total with taxes and fees
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
1 bedroom, iron/ironing board, WiFi (free), bed sheets

8. 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
9.8 out of 10, Exceptional, (17 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.
$273 nightly
The price is $305
Aug 17 - Aug 18
Total with taxes and fees
Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!
Living area

9. On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
8.0 out of 10, Very Good, (51 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
$275 nightly
The price is $315
Aug 23 - Aug 24
Total with taxes and fees
On River/Harvard Sq. two blocks
Front of property

10. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (405 reviews)
"Easy to move-in, location is good for traveler. The shower room not that clean, some hair from previous guests, just clean it can be manage by guest."
Taiwan
LICHIEH
$232 nightly
The price is $267
Aug 25 - Aug 26
Total with taxes and fees
Maverick Suites at 28 Fenway
1 bedroom, desk, iron/ironing board, internet

11. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.6 out of 10, Good, (15 reviews)
"All good, would definitely stay again"
United States
Dan C.
$217 nightly
The price is $255
Aug 16 - Aug 17
Total with taxes and fees
Cozy Studio Steps from Boston Common and Theaters
TV

12. Stunning 1BR | Steps to Fenway!

Stunning 1BR | Steps to Fenway!
Fenway–Kenmore
9.0 out of 10, Wonderful, (2 reviews)
"Nice place, good location. Would definitely stay again!"
United States
Amy K.
$241 nightly
The price is $311
Aug 16 - Aug 17
Total with taxes and fees
Stunning 1BR | Steps to Fenway!
1 bedroom, desk, iron/ironing board, WiFi

13. Downtown Studio | Students Welcome | W/D in unit

Downtown Studio | Students Welcome | W/D in unit
Downtown Boston
9.4 out of 10, Exceptional, (3 reviews)
"Was worth the price all around"
United States
steven l.
$219 nightly
The price is $283
Aug 20 - Aug 21
Total with taxes and fees
Downtown Studio | Students Welcome | W/D in unit
Smart TV, books

14. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (40 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
$259 nightly
The price is $298
Aug 16 - Aug 17
Total with taxes and fees
Bright 2BR by Boston Waterfront
Exterior

15. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (9 reviews)
"It was a great stay!"
United States
Adina S.
$220 nightly
The price is $284
Aug 19 - Aug 20
Total with taxes and fees
Light-filled Studio | Back Bay
Exterior

16. Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!

Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Downtown Boston
9.0 out of 10, Wonderful, (2 reviews)
"Host was very communicative. The apartment was very clean and spacious and the location was fantastic! A lot of things in walking distance and train stop nearby for getting to other parts of the city was convenient. I would highly recommend this host and their space! Thank you for your hospitality! Would love to come back."
United States
Rachael M.
$253 nightly
The price is $326
Aug 20 - Aug 21
Total with taxes and fees
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
2 bedrooms, desk, iron/ironing board, WiFi

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, (9 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
$281 nightly
The price is $322
Aug 17 - Aug 18
Total with taxes and fees
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Interior

18. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (317 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$319 nightly
The price is $356
Aug 20 - Aug 21
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
1 bedroom, iron/ironing board, WiFi, bed sheets

19. Primo North End Studio

Primo North End Studio
North End
9.4 out of 10, Exceptional, (19 reviews)
"Great place, amazing location!"
United States
Christopher W.
$308 nightly
The price is $354
Aug 16 - Aug 17
Total with taxes and fees
Primo North End Studio
TV, offices

20. Studio in the Heart of Boston!

Studio in the Heart of Boston!
Downtown Boston
10.0 out of 10, Exceptional, (3 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.
$220 nightly
The price is $258
Aug 20 - Aug 21
Total with taxes and fees
Studio in the Heart of Boston!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

8/10 Good
"Clean room, helpful staff, "city view" room looked out at a large building across the street, so not much of a view. All in all, good clean hotel in a good location for exploring the city."
James 3-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Find out more about Winchester

Winchester Apartments information

Number of reviews
1,057
Accommodation
1444 Apartments
Lowest Price
$200
Highest Price
$407

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 4245 hotels and accommodations including 1557 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. 3bdrm Apt next to Airport/Downtown 7 min drive: It's situated in Chelsea, 7 mi/11.3 km away. Includes Smart TVs. Luxury Salem 2BR Apartment | Pool • Gym • Parking: Located 12.8 mi/20.5 km away in Salem. A private pool, separate dining areas, and Smart TVs are included. Access to a game room is available on site. Curated Designer Retreat • Pool • Gym • Dining: Located in Everett, 5.9 mi/9.5 km from Winchester. Includes a private pool, free WiFi, and separate dining areas. Access to a game room 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.

Explore a world of travel with Expedia