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Compare 1373 Apartments in Winchester with updated reviews, rates, and availability.

Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is SAR 372
SAR 795 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
Temple Place Suites
Room

Temple Place Suites

2.5 star property
6.8 out of 10, (175)
"I recently had the pleasure of staying at Temple Place Suites, and I can honestly say it you get what you pay for. The location is absolutely perfect, situated in the heart of the city, with easy access to vibrant neighborhoods, restaurants, and cultural landmarks. The suite is minimalistic and there’s a sense of homeliness. Spacious, impeccably clean, and tastefully decorated. The staff at Temple Place Suites went above and beyond to make my stay memorable. They were friendly, attentive, and...
The price is SAR 361
SAR 621 total
includes taxes & fees
23 Dec - 24 Dec
Temple Place Suites
Near scenic Fresh Pond, Charles river, shops, Harvard Sq access , Free parking
Sleeping area viewed from eating area

Near scenic Fresh Pond, Charles river, shops, Harvard Sq access , Free parking

9.2 out of 10, Wonderful, (93)
"Within walking distance of restaurants and shops. Also not very far from the bust system or subway."
Near scenic Fresh Pond, Charles river, shops, Harvard Sq access , Free parking
Panoramic view, large deck, ground floor apartment, walk to subway and beach
This terrace gets the morning sun.

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
Location+Comfort+Convenience
3 minute walk to this view (real picture, no filter)

Location+Comfort+Convenience

9.6 out of 10, Exceptional, (48)
"We loved the location and appreciated the proximity to the subway and airport. Unfortunately there is no designated parking and street parking on the weekends is very limited… the closest street parking we could find was 2 1/2 blocks away (kind of a bummer with a family of 4 and lots of luggage). I really should have read the reviews in advance… the stairs are narrow and steep so my teenager with a recent ACL replacement struggled slightly. The sloped floors would have been irritating for any...
Location+Comfort+Convenience
4BR/1BTH Easy Commute South Boston Apartment
Room

4BR/1BTH Easy Commute South Boston Apartment

The price is SAR 165
SAR 1,579 total
includes taxes & fees
7 Jan - 8 January 2025
4BR/1BTH Easy Commute South Boston Apartment
Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport
view from the sitting room

Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport

9.8 out of 10, Exceptional, (91)
"We had a great stay. We enjoyed our nice late afternoon walks on the beach to watch the sunset."
Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Full Kitchen

🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖

9.8 out of 10, Exceptional, (88)
"The property was great, close to family and friends. My only complaint was we were unable to figure out how to change the thermostat to cool the house down…user error? Maybe. "
🎖The Ashmont Apartment - Close to Subway & Downtown Boston🎖
Prima Boston North End 2brm
Private kitchen

Prima Boston North End 2brm

9.0 out of 10, Wonderful, (8)
"Fun area for walking and exploring. Wish we had done more research into parking! Host responded right away when the front door code didn’t work for us. We enjoyed our stay!"
Prima Boston North End 2brm
The Chester
Living area

The Chester

3.5 star property
8.6 out of 10, Excellent, (12)
"The historic brownstone had tremendous charm and was lovely. There was a problem with the heat not working and repeated requests for something to be done were met with conflicting information about possible repairs, but nothing was done. Luckily the temperatures rose during the day, which helped keep it a little more comfortable."
The Chester
Beautiful Retreat close to Downtown Boston. Pets friendly.
Living room.

Beautiful Retreat close to Downtown Boston. Pets friendly.

9.8 out of 10, Exceptional, (114)
"The stay was great. Owner was great at communications. Very clean. Easy drive into Boston. Needed more towels and wash cloths which the owner brought. "
The price is SAR 563
SAR 1,321 total
includes taxes & fees
27 Dec - 28 Dec
Beautiful Retreat close to Downtown Boston. Pets friendly.
Modern 2 BR, 1BA Near Convention Center & Seaport
Living area

Modern 2 BR, 1BA Near Convention Center & Seaport

9.8 out of 10, Exceptional, (150)
"Clean, spacious, great access to a majority of Boston "
The price is SAR 751
SAR 1,576 total
includes taxes & fees
5 Jan - 6 January 2025
Modern 2 BR, 1BA Near Convention Center & Seaport
Spacious Open Concept 1BD/1BATH In Boston City
Room

Spacious Open Concept 1BD/1BATH In Boston City

5.6 out of 10, (9)
"The unit is nice and spacious. Very clean. Interior decoration could really use some work. Furniture was cheap. There were exposed hanging hooks all over the bedroom. But other than that it’s quite comfortable. Very strange third party check-in process. Coffee machine didn’t work. Did not provide dishwasher pods or coffee filters. But the real issue is the location. Area feels dangerous. Plan your days carefully and make sure to get a car whenever you leave the unit."
The price is SAR 165
SAR 813 total
includes taxes & fees
23 Dec - 24 Dec
Spacious Open Concept 1BD/1BATH In Boston City
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Exterior

Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

9.6 out of 10, Exceptional, (120)
"Lovely property. Very clean and convenient to everything. Comfortable furniture and nice kitchen. Good water pressure in shower. We highly recommend this property. We will stay again."
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
Living area

Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.

9.8 out of 10, Exceptional, (51)
"Everything about the cottage was great! We went to visit salem & it was just a short ride away. Everything we needed was close by. The house itself was so pretty. The host had everything you needed down to snacks & water when we arrived. Even coffee pods were included.( I'm pretty serious about my coffee). It was nice we didn't have to go out for anything upon arrival. Every room was comfortable & clean. The detail that was put into the cottage was impeccable. Would definitely stay here again &...
Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
The heart Cambridge/Boston Studio private yard free permit parking 1#
Private kitchen

The heart Cambridge/Boston Studio private yard free permit parking 1#

9.8 out of 10, Exceptional, (66)
"Your place was perfect for our needs and close enough to visit Fenway Park. We walked everywhere. The neighborhood was fine. Thank you for sharing your rental with us!"
The price is SAR 409
SAR 778 total
includes taxes & fees
3 Jan - 4 January 2025
The heart Cambridge/Boston Studio private yard free permit parking 1#
Gorgeous Oceanfront Penthouse
Interior

Gorgeous Oceanfront Penthouse

10.0 out of 10, Exceptional, (82)
"Very nice place, beautiful views and great location, especially if you like to walk along the beach. "
The price is SAR 695
SAR 1,325 total
includes taxes & fees
8 Jan - 9 January 2025
Gorgeous Oceanfront Penthouse
Downtown Studio Apt, Perfect for Medical Workers
Room

Downtown Studio Apt, Perfect for Medical Workers

3.4 out of 10, (10)
"The company has an absolutely insane process requiring multiple forms for verification, that are buggy, and check in and then you have to get a key at a gas station before they close, then take another Uber to the actual location. -- In over 100 short term rentals I've never experienced anything like this-- The place is a dive, there is more caulk holding up the walls in the bathroom than wood. The bathroom door barely opens. The sheets did appear clean and the bathroom sink, but the floors...
The price is SAR 229
SAR 896 total
includes taxes & fees
23 Dec - 24 Dec
Downtown Studio Apt, Perfect for Medical Workers
Luxury and Modern Apt near Mall/ Hospital
Living area

Luxury and Modern Apt near Mall/ Hospital

10.0 out of 10, Exceptional, (18)
"Loved this apartment CLEAN up to date awesome upgrades I loved the fridge!! haha It's the little things! Will be booking again!"
Luxury and Modern Apt near Mall/ Hospital
3 bedroom apartment next to T stop / off street parking
Living area

3 bedroom apartment next to T stop / off street parking

10.0 out of 10, Exceptional, (48)
"The rental was exactly as described. Beds were very comfortable. The house was very clean and uncluttered. Kitchen had full facilities. Loved the plants! The location was perfect for catching the trains/busses. We were a little hesitant when we got off the highway, thinking we had perhaps put the wrong address in as it did not immediately seem like there were apartments, but drive past the train station and there it was. I would definitely rent this place again."
The price is SAR 748
SAR 1,421 total
includes taxes & fees
30 Dec - 31 Dec
3 bedroom apartment next to T stop / off street parking
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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Other property types in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Private kitchen

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

7.4 out of 10, Good, (30)
"I give this place 3 stars, its a nice place with a good amount of room but there are a few issues. Our stay was Monday - Friday, just 2 adults. Pros - lots of room. Cons - no ac. There is a portable ac unit on wheels in the bedroom however, the exhaust vent goes behind a curtain to the window but not outside. There is no way to open the window for the exhaust vent to take the hot air outside so it just pumps all the hot air back into the room. Be prepared to wake up at 7:30am every morning...
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (405)
"Perfect location!"
The price is SAR 483
SAR 560 total
includes taxes & fees
23 Dec - 24 Dec
Sonder 907 Main
Maverick Suites at 28 Fenway
Lobby sitting area

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (156)
"Great stay. "
The price is SAR 372
SAR 795 total
includes taxes & fees
24 Dec - 25 Dec
Maverick Suites at 28 Fenway
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 3464 hotels and accommodations including 1813 apartments. Discover some favorite places in the larger area like Boston Common and TD Garden.
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?
Here are some of the more popular apartments in the area: Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93: Located in Winchester, 1.9 mi/3.1 km from the heart of Winchester. Includes laundry facilities, free WiFi, and separate dining areas. Access to a water park 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. Temple Place Suites: Located in Boston, 7.7 mi/12.4 km away. Includes free WiFi. Access to onsite laundry facilities is available on site. 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. Boston’s Finest New Renovated Apartment: It’s located in Boston, 11.7 mi/18.8 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?
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 Boston Common and TD Garden 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.