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

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, (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.
Private kitchen

2. 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.
$334 nightly
The price is $373
Sep 11 - Sep 12
Total with taxes and fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)

3. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (461 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
Living area

4. 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.
$199 nightly
The price is $222
Sep 7 - Sep 8
Total with taxes and fees
NEW Modern Apartment Near Boston & Harvard Square.
Interior

5. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (323 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
$291 nightly
The price is $325
Sep 7 - Sep 8
Total with taxes and fees
Near Boston Historic two-bedroom with Modern Amenities
Exterior

6. Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
9.0 out of 10, Wonderful, (15 reviews)
"Great option for long term stay!"
United States
Sophia
$283 nightly
The price is $304
Sep 11 - Sep 12
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
Living area

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.
$285 nightly
The price is $335
Sep 13 - Sep 14
Total with taxes and fees
Charming 1 Bedroom | Newbury Street
Exterior

8. 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
$241 nightly
The price is $283
Sep 20 - Sep 21
Total with taxes and fees
Stellar South End Studio
Exterior

9. Light-filled Studio | Back Bay

Light-filled Studio | Back Bay
Back Bay
9.6 out of 10, Exceptional, (11 reviews)
"It was a great stay!"
United States
Adina S.
$195 nightly
The price is $229
Sep 7 - Sep 8
Total with taxes and fees
Light-filled Studio | Back Bay
Interior

10. 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
$205 nightly
The price is $229
Sep 7 - Sep 8
Total with taxes and fees
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Room

11. Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
8.6 out of 10, Excellent, (8 reviews)
"Would stay again"
United States
mark p.
$209 nightly
The price is $240
Sep 7 - Sep 8
Total with taxes and fees
Studio Awaits Your Next Stay!
Living area

12. 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
$265 nightly
The price is $305
Sep 8 - Sep 9
Total with taxes and fees
Bright 2BR by Boston Waterfront
Private kitchen

13. 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.
$413 nightly
The price is $461
Sep 10 - Sep 11
Total with taxes and fees
3BR2Bth TD Garden/MIT/Harvard/BOS/3 Parking Spaces
Room

14. 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!
Living area

15. Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.2 out of 10, Very Good, (23 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
$209 nightly
The price is $240
Sep 7 - Sep 8
Total with taxes and fees
Perfect One Bedroom Stay In Downtown Boston!
Front of property

16. 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
$266 nightly
The price is $306
Sep 9 - Sep 10
Total with taxes and fees
Maverick Suites at 28 Fenway
Exterior

17. 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.
$209 nightly
The price is $240
Sep 7 - Sep 8
Total with taxes and fees
Studio in the Heart of Boston!
Room

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

Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Fenway–Kenmore
8.2 out of 10, Very Good, (13 reviews)
"Welcoming host, very responsive"
United States
Matthew G.
$283 nightly
The price is $324
Sep 10 - Sep 11
Total with taxes and fees
Free Parking 2 Bed 1 Bath Steps from BU/Kenmore
Interior

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.
$265 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
Bay Village Charming 1 Bedroom Apartment
Room

20. Pet Friendly - Laundry in Bldg - FIDI

Pet Friendly - Laundry in Bldg - FIDI
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"The property was in a fantastic location. We were able to enjoy all of down town Boston on foot. It was clean and comfortable. Our only complaint is that in the listing they say there is an elevator it doesn't mention that it is very unreliable. They do mention that in the check in information. We arrived very late into Boston 1030 pm and tried to use the elevator to get our luggage upstairs and we were stuck in the elevator for approximately 20 minutes before we finally got the door to...
United States
Kevin
$300 nightly
The price is $352
Sep 13 - Sep 14
Total with taxes and fees
Pet Friendly - Laundry in Bldg - FIDI
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"The location was great. People were friendly and nice. We would return when we get back to Boston"
Gordon 2-night trip
Posted less than an hour ago
The Dagny Boston

Find out more about Winchester

Winchester Apartments information

Number of reviews
1,460
Accommodation
1444 Apartments
Lowest Price
$200
Highest Price
$461

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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