Search Apartments in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 1806 Apartments in Winchester with updated reviews, rates, and availability.

Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (176)
"Amazing stay, thank you!"
The price is SAR 383
SAR 806 total
includes taxes & fees
13 Apr - 14 Apr
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (194)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is SAR 446
SAR 719 total
includes taxes & fees
24 Apr - 25 Apr
Temple Place Suites
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Terrace/patio

Beautiful studio in historic neighborhood of Boston. Super close to downtown!

10.0 out of 10, Exceptional, (26)
"I was in Boston for a mix of work/pleasure, and this location worked perfectly. A solid 30 minute walk from the city proper, but super rideshare accessible to anywhere you’d need to go. The hosts were quick to respond and eager to help with anything I needed, 10/10 would stay here again!"
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
On River/Harvard Sq. two blocks
Dining

On River/Harvard Sq. two blocks

2.0 star property
10.0 out of 10, Exceptional, (3)
"Cute apartment furnished with basic staples. Good location and free parking. Lots of stairs!"
The price is SAR 503
SAR 988 total
includes taxes & fees
15 Apr - 16 Apr
On River/Harvard Sq. two blocks
Downtown Crossing, Affordable Stay, Book Now!
TV, offices

Downtown Crossing, Affordable Stay, Book Now!

6.8 out of 10, (3)
"Good central location, clean functional space, fair price, responsive staff."
The price is SAR 672
SAR 1,156 total
includes taxes & fees
10 Apr - 11 Apr
Downtown Crossing, Affordable Stay, Book Now!
The Chester Hotel
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds

The Chester Hotel

3.5 star property
8.8 out of 10, Excellent, (14)
"Great stay, very clean, room aesthetic is beautiful, kitchenette with all necessities, proximity to a lot of good dining and coffee shops. Just be aware that it is not soundproof and . I will definitely always book for my Boston stays. "
The Chester Hotel
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Outdoor dining

Panoramic view, large deck, ground floor apartment, walk to subway and beach

9.4 out of 10, Exceptional, (86)
"Garden apartment unit that was clean, quiet and comfortable. Would stay again. "
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Glamorous Luxury Apartment, Near T
TV, offices

Glamorous Luxury Apartment, Near T

Glamorous Luxury Apartment, Near T
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Outdoor dining

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

The price is SAR 1,910
SAR 3,247 total
includes taxes & fees
11 Apr - 12 Apr
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Beautiful Retreat close to Downtown Boston. Pets friendly.
Pool

Beautiful Retreat close to Downtown Boston. Pets friendly.

9.8 out of 10, Exceptional, (118)
"This is the third time we have stayed here. As before, very clean, everything as described. Convenient location, parking. Supplies for the stay. Everything as expected. Hope to stay here again."
The price is SAR 702
SAR 1,496 total
includes taxes & fees
14 Apr - 15 Apr
Beautiful Retreat close to Downtown Boston. Pets friendly.
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Fridge, microwave, oven, stovetop

Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH

The price is SAR 3,002
SAR 4,681 total
includes taxes & fees
14 Apr - 15 Apr
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
BRAND NEW 3bds/2bths in a small & friendly neighborhood. Mins away from Boston.
Fridge, microwave, oven, stovetop

BRAND NEW 3bds/2bths in a small & friendly neighborhood. Mins away from Boston.

9.8 out of 10, Exceptional, (42)
"We needed a place to stay for a group of friends who were celebrating 2 great events, St. Paddy’s Day weekend and our friends’ engagement. This place was perfect for our group and was in a very convenient location. A"
BRAND NEW 3bds/2bths in a small & friendly neighborhood. Mins away from Boston.
Amazing price and location / parking -North End (M1S)
Lake

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

9.6 out of 10, Exceptional, (40)
"We bought tickets to a concert at TD and decided to make it a whole weekend getaway in the city so we needed a place to stay that made sense and didn't break the bank - and this place fit that bill! The price is super reasonable for Boston, the parking included was an added perk - and everything we wanted to do was either super walkable or a quick T ride away. I feel like we got a better feel for the city staying here than in a hotel. It was small for an apartment - but no smaller than some of...
The price is SAR 597
SAR 1,529 total
includes taxes & fees
8 Apr - 9 Apr
Amazing price and location / parking -North End (M1S)
Perfect North End Studio
1 bedroom, iron/ironing board, WiFi, bed sheets

Perfect North End Studio

9.4 out of 10, Exceptional, (19)
"My husband and I stayed in this darling little unit over St. Patrick’s Day weekend. It was clean, the bed is comfortable, the location is perfect and the host was extremely responsive. We will definitely stay at this location again when we return to Boston."
The price is SAR 619
SAR 1,368 total
includes taxes & fees
24 Apr - 25 Apr
Perfect North End Studio
Near Boston Historic two-bedroom with Modern Amenities
Terrace/patio

Near Boston Historic two-bedroom with Modern Amenities

10.0 out of 10, Exceptional, (251)
"This is a great spot for a group, comfortable and is beautiful. It has everything. "
The price is SAR 750
SAR 1,066 total
includes taxes & fees
6 Apr - 7 Apr
Near Boston Historic two-bedroom with Modern Amenities
60-2 Boston Stylish Apartment
Fridge, microwave, oven, stovetop

60-2 Boston Stylish Apartment

The price is SAR 597
SAR 1,509 total
includes taxes & fees
6 Apr - 7 Apr
60-2 Boston Stylish Apartment
NEW 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
Smart TV

NEW 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking

10.0 out of 10, Exceptional, (3)
"Cute little place. Loved the decor. The location was perfect for us. Just a short walk from the majority of our destinations (witch museum, memorial, Peabody museum, shopping etc.). Host was very responsive. We enjoyed our stay! "
The price is SAR 284
SAR 862 total
includes taxes & fees
9 Apr - 10 Apr
NEW 1BR on Salem Common l Steps to Witch Museum l Fenced in Yard + Parking
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
Smart TV, Netflix, Hulu, streaming services

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!

9.6 out of 10, Exceptional, (12)
"Had a great stay at this property. My wife and I needed a place to stay and work while some work was being done on our house. The apartment was plenty spacious for two. There are two comfortable bedrooms, a spacious, well-stocked and equipped kitchen, and a cozy living room to hang out in at night. We were very content working there during the day. The apartment is located in a quiet, walkable neighborhood and a short drive to Cambridge or Boston. The owner Lucas was very responsive to all...
The price is SAR 598
SAR 1,217 total
includes taxes & fees
7 Apr - 8 Apr
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
Renovated Retreat /Near JFK station
Private kitchen

Renovated Retreat /Near JFK station

2.0 star property
Renovated Retreat /Near JFK station
Exquisite North End 1brm
Private kitchen

Exquisite North End 1brm

9.6 out of 10, Exceptional, (12)
"I took my son to Boston for his 13th birthday. This clean & tidy apartment was perfect for the two of us. We were able to walk to all tourists spots. Wonderful restaurants & parks nearby. We felt very safe & comfortable. Highly recommend. "
The price is SAR 582
SAR 1,368 total
includes taxes & fees
27 Apr - 28 Apr
Exquisite North End 1brm
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (452)
"Very comfortable room and close to everything."
The price is SAR 619
SAR 718 total
includes taxes & fees
13 Apr - 14 Apr
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (176)
"Amazing stay, thank you!"
The price is SAR 383
SAR 806 total
includes taxes & fees
13 Apr - 14 Apr
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (194)
"The bed is super comfortable, self check in instructions are clear. Microwave, fridge, hairdryer and coffee maker all work excellently. The only downside is the shower hot water takes forever to start, and the heater is very noisy. It’s also close to the road, so the noises from the construction and roads are very noisy. Love the fact there’s elevator. "
The price is SAR 446
SAR 719 total
includes taxes & fees
24 Apr - 25 Apr
Temple Place Suites
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.

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 3746 hotels and accommodations including 2055 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: Maverick Suites at 28 Fenway: Located in Boston, 7.7 mi/12.5 km from the heart of Winchester. Includes free WiFi and Smart TVs. Onsite laundry facilities and concierge services are on site. Temple Place Suites: Located 7.7 mi/12.4 km away in Boston. Amenities include free WiFi. Access to onsite laundry facilities is available on site. Beautiful studio in historic neighborhood of Boston. Super close to downtown!: It’s situated in Boston, 9.5 mi/15.2 km away. Includes free WiFi. Beautiful Retreat close to Downtown Boston. Pets friendly.: 12.3 mi/19.8 km away in Boston. Free WiFi, private balconies, and separate dining areas are included. The Chester Hotel: It’s located in Boston, 8.3 mi/13.4 km from Winchester. Includes free WiFi, premium mattresses, 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?
Family-friendly attractions include Winter Pond, whereas Middlesex Fells Reservation is a spot to enjoy the outdoors. 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.