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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 communication with hosts, perfect location for so many sites in the region, lovely space just as advertised. "
United States
Lynn C.
The price is CA $153
CA $343 total
includes taxes & fees
Aug 30 - Aug 31
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up)

2. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (451 reviews)
"Great location so close to everything"
United States
Hunter
The price is CA $130
CA $237 total
includes taxes & fees
Aug 31 - Sep 1
Temple Place Suites
Exterior

3. Sleek Studio Apartment in the South End

Sleek Studio Apartment in the South End
Back Bay
9.6 out of 10, Exceptional, (5 reviews)
"A little issue getting in with the door code operation but otherwise great"
United States
Unspecified U.
The price is CA $162
CA $383 total
includes taxes & fees
Aug 26 - Aug 27
Sleek Studio Apartment in the South End
Living area

4. 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
The price is CA $151
CA $441 total
includes taxes & fees
Aug 28 - Aug 29
Bright 2BR by Boston Waterfront
Interior

5. Perfetto North End 1brm

Perfetto North End 1brm
North End
9.8 out of 10, Exceptional, (16 reviews)
"Great location- excellent place!"
United States
Deborah S.
The price is CA $220
CA $511 total
includes taxes & fees
Aug 27 - Aug 28
Perfetto North End 1brm
Exterior

6. 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.
The price is CA $230
CA $503 total
includes taxes & fees
Aug 26 - Aug 27
Walk everywhere - Seaport, North End, Beacon Hill. Steps from MBTA public transit. Keyless Entry!
Front of property

7. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (410 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
The price is CA $209
CA $376 total
includes taxes & fees
Aug 27 - Aug 28
Maverick Suites at 28 Fenway
Room

8. Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
7.4 out of 10, Good, (16 reviews)
"All good, would definitely stay again"
United States
Dan C.
The price is CA $132
CA $397 total
includes taxes & fees
Aug 28 - Aug 29
Cozy Studio Steps from Boston Common and Theaters
Living area

9. On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
West Cambridge
7.8 out of 10, Good, (52 reviews)
"Very convenient for our stay with a grandson attending Harvard"
United States
Christy
The price is CA $235
CA $431 total
includes taxes & fees
Aug 26 - Aug 27
On River/Harvard Sq. two blocks
Interior

10. Near Boston Historic two-bedroom with Modern Amenities

Near Boston Historic two-bedroom with Modern Amenities
Malden
10.0 out of 10, Exceptional, (320 reviews)
"Place was spotless and had everything you needed for a great stay."
United States
Jenn K.
The price is CA $344
CA $484 total
includes taxes & fees
Sep 2 - Sep 3
Near Boston Historic two-bedroom with Modern Amenities
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.
The price is CA $187
CA $356 total
includes taxes & fees
Aug 30 - Aug 31
Studio Awaits Your Next Stay!
Property grounds

12. 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.
The price is CA $217
CA $397 total
includes taxes & fees
Sep 7 - Sep 8
Studio in the Heart of Boston!
Outdoor dining

13. Amazing price and location / parking -North End (M1S)

Amazing price and location / parking -North End (M1S)
North End
9.6 out of 10, Exceptional, (67 reviews)
"Very convenient location, it is really all you need for a nice vacation if you plan on seeing the city. The bed was very comfortable too."
United States
Michael
The price is CA $248
CA $561 total
includes taxes & fees
Aug 26 - Aug 27
Amazing price and location / parking -North End (M1S)
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.
The price is CA $201
CA $417 total
includes taxes & fees
Sep 21 - Sep 22
Stay in comfort and style! Encore Private Suite + Free parking! Close to Boston!
Room

15. Milk153-6F-1/1 · Spacious 1br In Boston FIDI | Close to T!

Milk153-6F-1/1 · Spacious 1br In Boston FIDI | Close to T!
Downtown Boston
10.0 out of 10, Exceptional, (1 review)
"The property was well appointed and a good value for the money. The in room laundry and separate bedroom along with a full kitchen, made everything more comfortable. The location is also convenient to many restaraunts for both dine in and take-out. "
United States
Susan B.
The price is CA $267
CA $552 total
includes taxes & fees
Aug 26 - Aug 27
Milk153-6F-1/1 · Spacious 1br In Boston FIDI | Close to T!
Room

16. Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway

Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Fenway–Kenmore
9.8 out of 10, Exceptional, (9 reviews)
The price is CA $191
CA $457 total
includes taxes & fees
Sep 6 - Sep 7
Simple 2 Bd/2 bth | Washer/Dryer | Close to Fenway
Room

17. Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.4 out of 10, Very good, (22 reviews)
"Very easy check in, great location to walk to the ballet. Tons of great bars around"
United States
Keith
The price is CA $187
CA $353 total
includes taxes & fees
Sep 1 - Sep 2
Perfect One Bedroom Stay In Downtown Boston!
Dining

18. 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, (68 reviews)
"Great location, close to public transport, the place is clean and owner was responsive"
United States
Dawn N.
The price is CA $241
CA $485 total
includes taxes & fees
Sep 16 - Sep 17
3 bedroom apartment next to T stop / off street parking
Interior

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

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
8.8 out of 10, Excellent, (20 reviews)
"Easy, clean and a comfortable stay"
United States
Justin P.
The price is CA $162
CA $311 total
includes taxes & fees
Sep 1 - Sep 2
Enjoyable 2-bedroom lower level apartment in charming Lynn
Living area

20. 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.
The price is CA $206
CA $346 total
includes taxes & fees
Sep 6 - Sep 7
NEW Modern Apartment Near Boston & Harvard Square.
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

Arcadian Hotel

Arcadian Hotel

8/10 Good
"Close to bus line, walkable to nearby stores and felt safe."
Pahoua 3-night trip
Posted less than an hour ago
Arcadian Hotel

Find out more about Winchester

Winchester Apartments information

Number of reviews
1,577
Accommodation
1444 Apartments
Lowest Price
CA $237
Highest Price
CA $561

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 4232 hotels and accommodations including 1587 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. Luxury Salem 2BR Apartment | Pool • Gym • Parking: Located in Salem, 12.8 mi/20.5 km away. Includes a private pool, separate dining areas, and Smart TVs. 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. 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.

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