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

Compare 1299 Apartments in Winchester with updated reviews, rates, and availability.

Temple Place Suites
Room
Temple Place Suites
2.5 star property
6.8 out of 10, (144)
"Overall the place is great if you’re on a budget, however someone kept clogging the bathroom and it barely flushed as it is. On the plus side there were two bathrooms to use. "
The price is SAR 540
SAR 828 total
includes taxes & fees
29 Sep - 30 Sep
Temple Place Suites
Maverick Suites at 28 Fenway
Lobby sitting area
Maverick Suites at 28 Fenway
2.5 star property
9.0 out of 10, Wonderful, (120)
"Clean, no frills place to stay."
The price is SAR 530
SAR 975 total
includes taxes & fees
22 Sep - 23 Sep
Maverick Suites at 28 Fenway
The Chester
Living area
The Chester
3.5 star property
9.0 out of 10, Wonderful, (8)
"I liked that it was in walking distance to Fenway Park and not far from other attractions. The bed was comfortable but it is a little noisy. The people upstairs were up all hours of the night. The water took a long time to heat up and was mostly lukewarm. "
The price is SAR 657
SAR 1,535 total
includes taxes & fees
22 Sep - 23 Sep
The Chester
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, (114)
"This property is in a great location in Salem, near restaurants, shops, and historic sites. The upstairs primary bedroom is very large and spacious. The listing says there were two bedrooms with queen beds, but the downstairs bedrooms are both small and each only have a double bed. The host was very responsive and helpful."
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
Modern 2BR/ Close to Boston with a lovely outdoor space
Living area
Modern 2BR/ Close to Boston with a lovely outdoor space
9.6 out of 10, Exceptional, (13)
"Easy to find, easy to check in. Inside was clean and spacious with all necessities available which made traveling easier on us. Thank you. Walking distance for food and coffee. :)"
Modern 2BR/ Close to Boston with a lovely outdoor space
<br>Danvers spacious apt near Salem historic witch town Mall / Hospital
Exterior
<br>Danvers spacious apt near Salem historic witch town Mall / Hospital
10.0 out of 10, Exceptional, (11)
"accurately photographed property that was comfortable and convenient."
The price is SAR 882
SAR 1,844 total
includes taxes & fees
24 Sep - 25 Sep
<br>Danvers spacious apt near Salem historic witch town Mall / Hospital
Stunning, Brand New, 2-bedroom apartment in Boston Framingham City Heart
Exterior
Stunning, Brand New, 2-bedroom apartment in Boston Framingham City Heart
6.0 out of 10, (1)
"Location was good. Close to T and easy to get to Boston. Stairs are steep in typical New England style. Shower door would not stay in place, so had to hold it with towel. The big issue was it had mice! The host gave us traps, but it was hard to enjoy with them scurrying around"
Stunning, Brand New, 2-bedroom apartment in Boston Framingham City Heart
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
Exterior
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
10.0 out of 10, Exceptional, (35)
"The calm of a typical and friendly residential neighborhood... less than 20-25 minutes (car + subway) from the heart of Boston was perfect for us. Orient Heights subway station is just 6 minutes from the house with an incentive parking lot at only $2.40 per 24 hours. This saved us the hassle of driving around the city while allowing us to come and go as we pleased. The residence and its two spacious bedrooms + dining and living rooms allowed us to be comfortable throughout our stay and there...
The price is SAR 747
SAR 1,429 total
includes taxes & fees
23 Sep - 24 Sep
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available
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, (79)
"We stayed here for 4 nights. The location is great as only a short walk to Savin Hill station which is on the red line with frequent trains into the centre of Boston. Approx 20 mins to Park Street which is stop for Boston Common, where the Freedom Trails begins. If you want to stay in a quieter location then this is definitely the place to stay. The accommodation is in need of updating but as we were out sightseeing most of the time, this did not bother us. We really liked the Savin Hill...
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Oceanfront, New England. November foliage. Book Thanksgiving now!
Guests kayaking in the bay, Boston Harbor Islands.
Oceanfront, New England. November foliage. Book Thanksgiving now!
9.4 out of 10, Exceptional, (112)
"Overall the property was perfect for out needs. Amazing location righr acroas the street from a small beach. Room for our 3 kids. Close to the ferry and Boston. Only cons are in the listing it says toys, video games, childrens kitchen things supplied. They are not. No body wash. And my husband had to run to home depot to fix one of the twin bedframes the first night there and repair the door knob to the master bedroom. O erall great experience. Amazing responsive kind host. "
Oceanfront, New England. November foliage. Book Thanksgiving now!
Ocean Front Beach Apartment, Close To Boston!
Exterior
Ocean Front Beach Apartment, Close To Boston!
9.8 out of 10, Exceptional, (32)
"Nice place to visit, clean house, everything available,access to the beach, quiet area , neighbor very friendly. We enjoyed the sunset We liked the house and we will recommend it. Sam and Reine "
Ocean Front Beach Apartment, Close To Boston!
Fresh New Space, Walk to Salem Harbor, Historic
You will feel relaxed in the queen Tuft and Needle mattresses in both bedrooms.
Fresh New Space, Walk to Salem Harbor, Historic
9.8 out of 10, Exceptional, (8)
"Loved our stay here! Paula was super friendly and helpful (and the chickens were lovely, too!). "
Fresh New Space, Walk to Salem Harbor, Historic
Beautiful Retreat close to Downtown Boston. Pets friendly.
Living room.
Beautiful Retreat close to Downtown Boston. Pets friendly.
9.8 out of 10, Exceptional, (105)
"The unit is clean, well stocked and convenient to eateries and stores. The host was great and easy to reach. Here’s something to consider, the Red Line proved to be difficult unless you were very familiar with the process. We had an aggressive male confront us and rambled on an on the whole trip. It was intimidating to say the least. As a single woman, I’d Uber next time from the airport."
The price is SAR 679
SAR 1,484 total
includes taxes & fees
20 Oct - 21 Oct
Beautiful Retreat close to Downtown Boston. Pets friendly.
Harvard Allston Executive Suite Loft
Dining
Harvard Allston Executive Suite Loft
9.8 out of 10, Exceptional, (6)
"Had a group of friends racing at Head of the Charles and this loft was in a perfect location. Walking distance to the river, food, coffee, and grocery stores. The host was communicative, very friendly, and the listing was accurate. Clean for the most part, quite, and we enjoyed our stay."
Harvard Allston Executive Suite Loft
Boston Spacious Apartment with private outdoor patio
Exterior
Boston Spacious Apartment with private outdoor patio
2.0 star property
Boston Spacious Apartment with private outdoor patio
🔥BLACK FRIDAY🔥597 Spacious, cozy 5BR apartment in Medford
Interior
🔥BLACK FRIDAY🔥597 Spacious, cozy 5BR apartment in Medford
2.0 star property
The price is SAR 822
SAR 2,008 total
includes taxes & fees
24 Sep - 25 Sep
🔥BLACK FRIDAY🔥597 Spacious, cozy 5BR apartment in Medford
Modern 2 BR, 1BA Near Convention Center & Seaport
Interior
Modern 2 BR, 1BA Near Convention Center & Seaport
9.8 out of 10, Exceptional, (138)
"Nice place. Communicative host. Thanks!"
The price is SAR 938
SAR 1,851 total
includes taxes & fees
6 Oct - 7 Oct
Modern 2 BR, 1BA Near Convention Center & Seaport
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, (83)
"A gorgeous setting so close to the beach and a quick drive to Salem and ferry to Boston. You couldn’t ask for a better location to just relax and go sightseeing. Host was wonderful , would definitely recommend and stay there again! "
Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport
Friendly family with. Sweet home
Property grounds
Friendly family with. Sweet home
8.4 out of 10, Very Good, (15)
"Used rental to visit Salem with teens. It was close enough to walk to attractions.Not plush but served our purpose. Confortable beds."
Friendly family with. Sweet home
Quiet neighborhood and Walking destination to Downtown Salem
Exterior
Quiet neighborhood and Walking destination to Downtown Salem
9.4 out of 10, Exceptional, (3)
"Easy instructions to get into the apartment, we were on the third floor. Great amenities, and it was a nice quiet place. Nice furnishings as well."
Quiet neighborhood and Walking destination to Downtown Salem
Don't see what you're looking for?
See all available properties in Winchester
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.
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

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, (28)
"This place was perfect for our Salem visit. Easy to find and convenient for a quick trip to the store. The neighborhood was nice."
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
Maverick Suites at 28 Fenway
Lobby sitting area
Maverick Suites at 28 Fenway
2.5 star property
9.0 out of 10, Wonderful, (120)
"Clean, no frills place to stay."
The price is SAR 530
SAR 975 total
includes taxes & fees
22 Sep - 23 Sep
Maverick Suites at 28 Fenway
HYATT house Boston/Burlington
Pool
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2275)
"Great place to stay. Nice and quiet and new surroundings. "
The price is SAR 589
SAR 658 total
includes taxes & fees
29 Sep - 30 Sep
HYATT house Boston/Burlington
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 3234 hotels and accommodations including 1655 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?
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. Amenities include free WiFi. 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. Fantastic 2 Bedroom Apartment Near Downtown: It’s located in Boston, 12.1 mi/19.4 km from Winchester. Includes free WiFi, private balconies, and separate dining areas.
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. Average annual precipitation for Winchester is 49 inches.
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.