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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare 1374 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, (162)
"Unique interesting space. "
The price is SAR 450
SAR 884 total
includes taxes & fees
3 Feb - 4 Feb
Maverick Suites at 28 Fenway
Temple Place Suites
Room

Temple Place Suites

2.5 star property
6.8 out of 10, (181)
"The room was ok. The common kitchen was usually dirty and without enough utensils and cutery. Is difficult to get hot water in the shower, sometimes it is ok and some others it is cold"
The price is SAR 324
SAR 579 total
includes taxes & fees
17 Feb - 18 Feb
Temple Place Suites
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, (53)
"This was a great place to stay- the only negative I can say is if you are in the bottom unit you can hear people upstairs especially if they have on heels- so if you have an opportunity to request the top floor do!There were also random hairs in the beds which we did not like but otherwise the place was clean!! And really cute! Would definitely stay again and would totally recommend."
Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
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, (50)
"Convenient, clean, comfortable, spacious"
The price is SAR 746
SAR 1,427 total
includes taxes & fees
3 Feb - 4 Feb
3 bedroom apartment next to T stop / off street parking
On River/Harvard Sq. two blocks
Room

On River/Harvard Sq. two blocks

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cute apartment furnished with basic staples. Good location and free parking. Lots of stairs!"
The price is SAR 446
SAR 914 total
includes taxes & fees
4 Feb - 5 Feb
On River/Harvard Sq. two blocks
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
Prima Boston North End 2brm
Private kitchen

Prima Boston North End 2brm

9.0 out of 10, Wonderful, (10)
"Place was great for a quick two day trip to the North End! Perfect for our family!"
Prima Boston North End 2brm
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, (122)
"Loved staying here for my Christmas break in Witch City. Love the place and can't beat the location. Look forward to my next trip and hope to be able to stay here again.Thank you!"
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!
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 446
SAR 828 total
includes taxes & fees
9 Feb - 10 Feb
The heart Cambridge/Boston Studio private yard free permit parking 1#
60-1-Spring Getaway 10%! Newly built apt in Boston
Miscellaneous

60-1-Spring Getaway 10%! Newly built apt in Boston

60-1-Spring Getaway 10%! Newly built apt in Boston
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
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Miscellaneous

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston

The price is SAR 671
SAR 1,867 total
includes taxes & fees
5 Feb - 6 Feb
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Spacious 3BR in The Center of Downtown Boston! Family Favorite!
Living Room

Spacious 3BR in The Center of Downtown Boston! Family Favorite!

10.0 out of 10, Exceptional, (22)
"Very roomy and very clean. Apartment is bigger than it looks in the pictures. The location is incredibly convenient and just around the corner from a great grocery store. Communication with Amy was excellent! Would definitely stay here again."
Spacious 3BR in The Center of Downtown Boston! Family Favorite!
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
Miscellaneous

60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston

The price is SAR 521
SAR 1,427 total
includes taxes & fees
10 Feb - 11 Feb
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
Luxury and Modern Apt near Mall/ Hospital
Living area

Luxury and Modern Apt near Mall/ Hospital

10.0 out of 10, Exceptional, (22)
"One of the nicest places I’ve stayed in and we use Vrbo a lot. Nice quiet street too. Easy access to 128, close to supermarkets, etc. "
Luxury and Modern Apt near Mall/ Hospital
Gorgeous Oceanfront Penthouse
Interior

Gorgeous Oceanfront Penthouse

10.0 out of 10, Exceptional, (84)
"I booked this VRBO as part of my partner's Christmas gift trip to a Patriots game and we couldn’t have been happier with the space - beautifully decorated, stunning views, and well-appointed. A great spot for a day trip over to Salem and a drive over to Foxboro. (The only thing that would've made it better would have been a Bills win!) It "
The price is SAR 731
SAR 1,369 total
includes taxes & fees
9 Feb - 10 Feb
Gorgeous Oceanfront Penthouse
3 bedroom condo nestled in Historic fishing village - dog friendly
Island with seating for 2

3 bedroom condo nestled in Historic fishing village - dog friendly

9.6 out of 10, Exceptional, (58)
"Blaney St apartment was exactly as promised and was ideal for my family and me. We were visiting family in Swampscott so the location was perfect for us. We had one issue with a trash odor which was responded to immediately. Appreciate the location and ample space. Recommend if you want to be near the water in a lovely town. "
3 bedroom condo nestled in Historic fishing village - dog friendly
Waterfront Boston and island views Kayaks onsite Book summer'25 Weekly discounts
Guests kayaking in the bay, Boston Harbor Islands.

Waterfront Boston and island views Kayaks onsite Book summer'25 Weekly discounts

9.4 out of 10, Exceptional, (120)
"This was a great stay. We travel often and always use VRBO. We loved the quirky floors of the old building. Took me back to my childhood in my grampas farm house. Then when I learned the history of the property, I fell in love. Definitely recommend for families "
Waterfront Boston and island views Kayaks onsite Book summer'25 Weekly discounts
Central Boston Beacon Hill 2brm
Living area

Central Boston Beacon Hill 2brm

9.0 out of 10, Wonderful, (8)
"This apartment is in a key location and it well appointed and very clean! Very responsive and was able to get in to stow bags early!"
The price is SAR 596
SAR 1,449 total
includes taxes & fees
18 Feb - 19 Feb
Central Boston Beacon Hill 2brm
Boston 2 level luxury home, Free Parking, 5 mins to casino & 10 mins to airport
Living area

Boston 2 level luxury home, Free Parking, 5 mins to casino & 10 mins to airport

9.8 out of 10, Exceptional, (46)
"We stayed for our friends and family Annual New years eve getaway. 4 couples plus kids. The place was clean, easy to find, plenty ofclose walking distance to anything you would need. We didn't go to the casino but it's 5 mins away, 10 mins to Boston easy access. Kids had a blast with the arcade machine and snacks provided. Parents enjoyed the space and having the kids occupied.The owner was easily reachable for any questions and did a good job communicating. Would stay here again! "
Boston 2 level luxury home, Free Parking, 5 mins to casino & 10 mins to airport
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

Sonder 907 Main
Room

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (427)
"The checkin and room key code access process is a little weird with needing to use an an app or complete it on their website, but other than that, it was a pleasant stay in a convenient part of town."
The price is SAR 528
SAR 612 total
includes taxes & fees
17 Feb - 18 Feb
Sonder 907 Main
No. 284 powered by Sonder
Room

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (860)
"It was a great location, clean and affordable "
The price is SAR 520
SAR 613 total
includes taxes & fees
26 Feb - 27 Feb
No. 284 powered by Sonder
Global Luxury Suites Downtown Boston
Living room

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (525)
"It’s set up like an air b and b so the kitchen was really nice for our group"
The price is SAR 412
SAR 930 total
includes taxes & fees
5 Feb - 6 Feb
Global Luxury Suites Downtown Boston
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 3612 hotels and accommodations including 1959 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. Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.: It’s located in Everett, 5.5 mi/8.8 km away. On River/Harvard Sq. two blocks: 5.4 mi/8.7 km away in Cambridge. Beautiful Retreat close to Downtown Boston. Pets friendly.: It’s located in Boston, 12.3 mi/19.8 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. 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.