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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 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, (189)
"The property was nice. I was a little amused at the size but it was perfect. There was a "
The price is SAR 383
SAR 806 total
includes taxes & fees
30 Apr - 1 May
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, (199)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is SAR 495
SAR 776 total
includes taxes & fees
28 Apr - 29 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, (28)
"Property was great for just me and had all the amenities I needed (minus laundry but that was walking distance away). "
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
9.6 out of 10, Exceptional, (5)
"Conveniently located. Nice view of the river. Good space for 4 people. "
The price is SAR 503
SAR 983 total
includes taxes & fees
28 Apr - 29 Apr
On River/Harvard Sq. two blocks
Downtown Crossing, Affordable Stay, Book Now!
TV, offices

Downtown Crossing, Affordable Stay, Book Now!

5.8 out of 10, (6)
"Good central location, clean functional space, fair price, responsive staff."
The price is SAR 671
SAR 1,173 total
includes taxes & fees
28 Apr - 29 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, (15)
"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, (88)
"Lovely space, perfect for two people. Clean and charming. Within easy walking distance to restaurants, coffee shops and the T. Safe and quiet area. Host was incredibly helpful and very responsive. "
Panoramic view, large deck, ground floor apartment, walk to subway and beach
Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport
On the beach, sun loungers

Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport

9.8 out of 10, Exceptional, (92)
"Amazing views, property owner was very accommodating and pleasant to work with. Will be trying to return here in warmer weather."
Spectacular OCEANFRONT apt near BOSTON, SALEM + Logan Airport
Glamorous Luxury Apartment, Near T
TV, offices

Glamorous Luxury Apartment, Near T

10.0 out of 10, Exceptional, (4)
"We had a lot of family in for the Boston Marathon. The house worked out well for that, good location a short walk from the T. Also worked out well for hosting Easter with a nice kitchen. It's a short walk to the Whole Foods, Jamaica Pond, and Franklin Park. We were able to drive downtown, to Brighton, to Brookline, and to Newton without too much difficulty.Host was very responsive. One issue was the description of how to get into the unit wasn't correct; it talked about the third floor when the...
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 1,909
SAR 3,247 total
includes taxes & fees
4 May - 5 May
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, (119)
"Nice property, outside of the city but not too far, TV flickered when turned on, no laundry (but did not expect it), jetted tub did not work, upstairs residents EXTREMELY loud at night, overall ok stay"
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

10.0 out of 10, Exceptional, (1)
"If you can’t do stairs this probably isn’t for you. But everything else was really cool. The neighborhood was storybook and very walkable. It was very nice to stay here."
The price is SAR 1,609
SAR 2,855 total
includes taxes & fees
7 May - 8 May
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, (44)
"This apartment was a great stay for my family of 4. All the bedrooms were spacious and comfortable, the kitchen was pristine with dishwasher and automated ice machine in fridge, in unit washer and drier was a huge plus, and the location was perfect for everything we wanted to do while in Boston. Unfortunately I would recommend another location if staying with small children. Our daughter is 8 months old at the time of booking and the upstairs neighbors played extremely loud music late into the...
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, (41)
"Great location that was very convenient to all we wanted to do. "
The price is SAR 596
SAR 1,504 total
includes taxes & fees
28 Apr - 29 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

9.6 out of 10, Exceptional, (22)
"We chose this property for a two day visit to Boston. The neighborhood is historic and vibrant with lots to explore. This studio apartment was spotlessly clean, charmingly decorated and very comfortable. It is everything we expected and needed it to be."
The price is SAR 563
SAR 1,298 total
includes taxes & fees
30 Apr - 1 May
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, (256)
"Booked our stay to attend a concert at Roadrunner in Boston which was an easy Uber ride away. Mark was very kind and allowed us to check in early, the courtyard behind the house was beautiful with a cozy patio furniture to relax in. The house was spotless and beds were very comfortable. Will absolutely book again for future Boston endeavors. Highly recommend!"
The price is SAR 938
SAR 1,309 total
includes taxes & fees
28 Apr - 29 Apr
Near Boston Historic two-bedroom with Modern Amenities
60-2 Newly Built & Lovely Apartment in Boston
Fridge, microwave, oven, stovetop

60-2 Newly Built & Lovely Apartment in Boston

10.0 out of 10, Exceptional, (1)
The price is SAR 521
SAR 1,414 total
includes taxes & fees
28 Apr - 29 Apr
60-2 Newly Built & Lovely Apartment in Boston
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
Smart TV, Netflix, Hulu, streaming services

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

9.4 out of 10, Exceptional, (13)
"Loved the neighborhood "
The price is SAR 413
SAR 993 total
includes taxes & fees
5 May - 6 May
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, (14)
"Exceptional!"
The price is SAR 1,069
SAR 2,005 total
includes taxes & fees
19 May - 20 May
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.
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Other property types in Winchester

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (467)
"Great Location! Nice rooms. Nice Bar at the lobby and the rooftop"
The price is SAR 710
SAR 824 total
includes taxes & fees
26 May - 27 May
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, (189)
"The property was nice. I was a little amused at the size but it was perfect. There was a "
The price is SAR 383
SAR 806 total
includes taxes & fees
30 Apr - 1 May
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, (199)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is SAR 495
SAR 776 total
includes taxes & fees
28 Apr - 29 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 3717 hotels and accommodations including 2071 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 Retreat close to Downtown Boston. Pets friendly.: It’s situated in Boston, 12.3 mi/19.8 km away. Includes free WiFi, private balconies, and separate dining areas. The Chester Hotel: 8.3 mi/13.4 km away in Boston. Free WiFi, premium mattresses, and Smart TVs are included. Beautiful studio in historic neighborhood of Boston. Super close to downtown!: It’s located in Boston, 9.5 mi/15.2 km from Winchester. Includes free WiFi.
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.