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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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, (198)
"Amazing stay, thank you!"
The price is AED 588
AED 1,034 total
includes taxes & fees
27 May - 28 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, (209)
"Perfect location next to Boston Common. The room was spacious and clean, as were the communal bathrooms. The building itself looked tired in places (e.g. peeling wallpaper) but the location more than made up for it."
The price is AED 437
AED 704 total
includes taxes & fees
20 May - 21 May
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, (30)
"Great place is very clean very attentive staff"
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
9.2 out of 10, Wonderful, (11)
"Conveniently located. Nice view of the river. Good space for 4 people. "
The price is AED 694
AED 1,236 total
includes taxes & fees
26 May - 27 May
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, (7)
"Great location!"
The price is AED 536
AED 993 total
includes taxes & fees
26 May - 27 May
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)
"We really enjoyed our stay here and the space felt very welcoming. Thank you!"
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, (92)
"Place was excellent and well stocked, exactly as shown in pics, very comfortable. Good instructions to get in. Only down side was TV not working and got a $40 parking ticket (only street parking available)"
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, (95)
"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
Glamorous Luxury Apartment, Near T
TV, offices

Glamorous Luxury Apartment, Near T

10.0 out of 10, Exceptional, (7)
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

10.0 out of 10, Exceptional, (1)
"The apartment was clean, spacious and close lots of stores and restaurants "
The price is AED 1,870
AED 3,179 total
includes taxes & fees
30 May - 31 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, (120)
"Very clean, organized, and set up wonderfully for a 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

9.0 out of 10, Wonderful, (2)
"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 AED 2,935
AED 4,577 total
includes taxes & fees
31 May - 1 Jun
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.

9.6 out of 10, Exceptional, (46)
"This place was extremely clean and host was friendly and responsive."
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, (43)
"Sweet little apartment in a great location. "
The price is AED 841
AED 1,805 total
includes taxes & fees
27 May - 28 May
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, (23)
"Loved the location and accessibility to everything. "
The price is AED 643
AED 1,402 total
includes taxes & fees
26 May - 27 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, (257)
"We have stayed here a number of times. Mark's place is clean, quiet, and convenient. Coming from Vermont to go to various difficult medical appointments at Tufts and BGH. we are always grateful for these comfortable accommodations. Thanks, Mark! aearegrateful tfir the comfortable "
The price is AED 918
AED 1,289 total
includes taxes & fees
19 May - 20 May
Near Boston Historic two-bedroom with Modern Amenities
60-2 3BR - Boston Modern Apt near Museum
Fridge, microwave, oven, stovetop

60-2 3BR - Boston Modern Apt near Museum

10.0 out of 10, Exceptional, (1)
The price is AED 584
AED 1,490 total
includes taxes & fees
22 May - 23 May
60-2 3BR - Boston Modern Apt near Museum
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, (5)
"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! "
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!

9.4 out of 10, Exceptional, (13)
"Close to Tufts & so well appointed. Everything we could ask for in accommodations away from home!"
The price is AED 606
AED 1,227 total
includes taxes & fees
19 May - 20 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
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

907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Lobby lounge

907 Main Hotel Central Square, Sonder by Marriott Bonvoy

4.0 star property
8.2 out of 10, Very Good, (479)
"The location was great. Close to the metro and good dining options. "
The price is AED 815
AED 945 total
includes taxes & fees
26 May - 27 May
907 Main Hotel Central Square, Sonder by Marriott Bonvoy
Global Luxury Suites Downtown Boston
Lobby lounge

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (551)
"Great place to stay, central and very secure"
The price is AED 517
AED 1,045 total
includes taxes & fees
26 May - 27 May
Global Luxury Suites Downtown Boston
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, (209)
"Perfect location next to Boston Common. The room was spacious and clean, as were the communal bathrooms. The building itself looked tired in places (e.g. peeling wallpaper) but the location more than made up for it."
The price is AED 437
AED 704 total
includes taxes & fees
20 May - 21 May
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 3698 hotels and accommodations including 2032 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: Temple Place Suites: Located in Boston, 7.7 mi/12.4 km from the heart of Winchester. Includes free WiFi. Access to onsite laundry facilities 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. Perfect North End Studio: It’s situated in Boston, 7.3 mi/11.8 km away. Includes Smart TVs. 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.