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 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (62 reviews)
"Excellent communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
$235 nightly
The price is $262
Aug 10 - Aug 11
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.
$349 nightly
The price is $390
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
8.4 out of 10, Very Good, (29 reviews)
"Friendly hosts"
United States
Jan
$200 nightly
The price is $218
Aug 10 - Aug 11
Total with taxes and fees
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Exterior

4. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location! On a quiet street right in the heart of the Back Bay. Can easily walk to restaurants, grocery stores, the Prudential Center, and pubic transportation. Close to the nearby colleges which was helpful for our stay. We were able to support our college-age kid through a tough moment. It was clean, comfortable, and management was responsive and friendly. It was easy in and out. We’ll definitely come back. This would be perfect if you had any kind of medical emergency or needed to...
United States
Gretchen J.
$195 nightly
The price is $251
Aug 10 - Aug 11
Total with taxes and fees
Light-filled Studio | Back Bay
2 bedrooms, WiFi, bed sheets

5. Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
West Cambridge
8.6 out of 10, Excellent, (38 reviews)
"Perfect location to explore Cambridge."
United States
Anonymous traveler
$277 nightly
The price is $317
Aug 9 - Aug 10
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks
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
7.0 out of 10, Good, (433 reviews)
"Great location so close to everything"
United States
Hunter
$164 nightly
The price is $189
Aug 9 - Aug 10
Total with taxes and fees
Temple Place Suites
TV

7. Stunning 1BR | Steps to Fenway!

Stunning 1BR | Steps to Fenway!
Fenway–Kenmore
10.0 out of 10, Exceptional, (1 review)
"Nice place, good location. Would definitely stay again!"
United States
Amy K.
$240 nightly
The price is $310
Aug 10 - Aug 11
Total with taxes and fees
Stunning 1BR | Steps to Fenway!
Coffee/tea maker, fridge, microwave, oven

8. 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.
$377 nightly
The price is $421
Aug 16 - Aug 17
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
1 bedroom, desk, iron/ironing board, internet

9. 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.
$228 nightly
The price is $268
Aug 11 - Aug 12
Total with taxes and fees
Cozy Studio Steps from Boston Common and Theaters
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, (402 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
$237 nightly
The price is $273
Aug 10 - Aug 11
Total with taxes and fees
Maverick Suites at 28 Fenway
TV

11. 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.
$259 nightly
The price is $334
Aug 11 - Aug 12
Total with taxes and fees
Charming 1 Bedroom | Newbury Street
Interior

12. 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.
$190 nightly
The price is $213
Aug 10 - Aug 11
Total with taxes and fees
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Interior

13. 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.
$320 nightly
The price is $357
Aug 12 - Aug 13
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
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
$269 nightly
The price is $309
Aug 10 - Aug 11
Total with taxes and fees
Bright 2BR by Boston Waterfront
Apartment, 2 Bedrooms | WiFi (free)

15. Luxury 2BR near Cambridge

Luxury 2BR near Cambridge
3.0 star property
Prospect Hill
6.8 out of 10, (3 reviews)
"Great apartment but the building's main door was malfunctioning and we could only get in when a resident with a key entered/exited. Also the wifi didn't work. The provider sis not offer any support or compensation, otherwise this would have been a perfect stay."
United States
Yonatan
$313 nightly
The price is $349
Aug 10 - Aug 11
Total with taxes and fees
Luxury 2BR near Cambridge
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.
$280 nightly
The price is $361
Aug 20 - Aug 21
Total with taxes and fees
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Interior

17. Bay Village Charming 1 Bedroom Apartment

Bay Village Charming 1 Bedroom Apartment
Bay Village
9.0 out of 10, Wonderful, (6 reviews)
"Great location and easy to navigate from check in to check out. Would stay again "
United States
Jennifer K.
$262 nightly
The price is $338
Aug 12 - Aug 13
Total with taxes and fees
Bay Village Charming 1 Bedroom Apartment
Living area

18. 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
$294 nightly
The price is $336
Aug 23 - Aug 24
Total with taxes and fees
On River/Harvard Sq. two blocks
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.
$309 nightly
The price is $355
Aug 16 - Aug 17
Total with taxes and fees
Primo North End Studio
1 bedroom, desk, iron/ironing board, WiFi

20. 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.
$254 nightly
The price is $327
Aug 18 - Aug 19
Total with taxes and fees
Downtown Studio | Students Welcome | W/D in unit
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Excellent"
Cassandra Elizabeth 1-night trip
Posted less than an hour ago
Hyatt Regency Boston/Cambridge

Find out more about Winchester

Winchester Apartments information

Number of reviews
Accommodation
 Apartments
Lowest Price
Highest Price

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 4258 hotels and accommodations including 1521 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. Salem Haunted Happenings Retreat: 13.3 mi/21.4 km away in Salem. Enjoyable 2-bedroom lower level apartment in charming Lynn: It's located in Lynn, 10 mi/16 km from Winchester. Includes free WiFi and Smart TVs.
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