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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Apartments in Winchester

Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi

Maverick Suites at 28 Fenway

3.0 star property
8.8 out of 10, Excellent, (284)
"Great location"
The price is AED 468
AED 897 total
includes taxes & fees
28 Oct - 29 Oct
Maverick Suites at 28 Fenway
30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo
Fridge, microwave, oven, stovetop

30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo

2.0 star property
9.6 out of 10, Exceptional, (9)
"This is a very convenient and comfortable place."
The price is AED 278
AED 1,084 total
includes taxes & fees
6 Oct - 7 Oct
30/3 - 3BR Boston - Cozy Apt near Franklin Park Zoo
Temple Place Suites
Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi

Temple Place Suites

2.5 star property
7.0 out of 10, Good, (278)
"Very convenient place to stay, near transportation and waking distance to historic points and shopping. "
The price is AED 473
AED 776 total
includes taxes & fees
29 Oct - 30 Oct
Temple Place Suites
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Marina

Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

2.0 star property
10.0 out of 10, Exceptional, (11)
"We were in the area visiting family and this studio was perfect for our needs. Spotless, comfortable and you can't beat the location. Robert was an outstanding host, most welcoming and made our stay perfect. We only hope it's available for our future visits."
The price is AED 643
AED 1,173 total
includes taxes & fees
15 Oct - 16 Oct
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown
Studio Awaits Your Next Stay!
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

10.0 out of 10, Exceptional, (3)
"Would stay again"
The price is AED 749
AED 1,274 total
includes taxes & fees
23 Oct - 24 Oct
Studio Awaits Your Next Stay!
Perfect One Bedroom Stay In Downtown Boston!
1 bedroom, desk, iron/ironing board, WiFi

Perfect One Bedroom Stay In Downtown Boston!

8.6 out of 10, Excellent, (14)
"Easy and clean. Great location close to everything!"
The price is AED 657
AED 1,188 total
includes taxes & fees
5 Oct - 6 Oct
Perfect One Bedroom Stay In Downtown Boston!
The Chester: Modern, Cool, Heart Of South End
1 bedroom, WiFi, bed sheets

The Chester: Modern, Cool, Heart Of South End

2.0 star property
The price is AED 779
AED 1,533 total
includes taxes & fees
5 Oct - 6 Oct
The Chester: Modern, Cool, Heart Of South End
Primo North End Studio
1 bedroom, iron/ironing board, WiFi, bed sheets

Primo North End Studio

9.0 out of 10, Wonderful, (11)
"Accurate listing, very clean and comfortable. Perfect location to great food, history, and transportation."
Primo North End Studio
2-bedroom apartment in enchanting seaport boston
Interior

2-bedroom apartment in enchanting seaport boston

2.0 star property
The price is AED 1,466
AED 2,892 total
includes taxes & fees
4 Oct - 5 Oct
2-bedroom apartment in enchanting seaport boston
Studio in the Heart of Boston!

Studio in the Heart of Boston!

10.0 out of 10, Exceptional, (1)
"My stay was excellent! One of the best parts was how responsive the property management team was to communicate with me so quickly on the VRBO app."
The price is AED 657
AED 1,140 total
includes taxes & fees
5 Oct - 6 Oct
Studio in the Heart of Boston!
Stylish Affordable Downtown Boston Studio!
Exterior

Stylish Affordable Downtown Boston Studio!

7.2 out of 10, Good, (5)
"Great place for a weekend get away... great location to catch the subway. Near great shopping, grocery, restaurants, theater and Boston Commons."
The price is AED 650
AED 1,144 total
includes taxes & fees
20 Oct - 21 Oct
Stylish Affordable Downtown Boston Studio!
Prime Central 1brm in North End Boston
Fridge, microwave, oven, stovetop

Prime Central 1brm in North End Boston

9.4 out of 10, Exceptional, (21)
"Great location near the Old North Church and the Freedom Trail. Only a couple of blocks from the harbor. The host is very responsive and accommodating. "
The price is AED 790
AED 1,621 total
includes taxes & fees
5 Oct - 6 Oct
Prime Central 1brm in North End Boston
Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines
Smart TV

Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines

10.0 out of 10, Exceptional, (1)
"Our stay in Beacon Hill was fabulous. Check in and communication with our host was flawless. David was quick to respond to all our questions and requests. The location was ideal. Two main subway lines were within 2-5 minute walk for longer destinations and we were able to walk to everything else. Small groceries, numerous restaurants, etc. We certainly had a memorable vacation and enjoyed our stay in David’s rental. "
The price is AED 687
AED 1,533 total
includes taxes & fees
14 Oct - 15 Oct
Beacon Hill Studio with Full Kitchen, Short Walk to MGH, Multiple Train Lines
Downtown Retreat: Stylish Boston Studio
1 bedroom, iron/ironing board, internet, bed sheets

Downtown Retreat: Stylish Boston Studio

8.2 out of 10, Very Good, (36)
"Excellent location for walking to all the sites!!!The communication was excellent! "
The price is AED 694
AED 1,520 total
includes taxes & fees
6 Oct - 7 Oct
Downtown Retreat: Stylish Boston Studio
Exquisite North End 1brm
Private kitchen

Exquisite North End 1brm

9.8 out of 10, Exceptional, (26)
"Great location, great communication with owner, clean, and perfect for our stay. "
The price is AED 1,010
AED 1,930 total
includes taxes & fees
31 Oct - 1 Nov
Exquisite North End 1brm
Perfect location Sleeps 3
TV, offices

Perfect location Sleeps 3

8.0 out of 10, Very Good, (11)
"Location was great. Communication was top notch. Place was small. Bathroom was small and shower not great. 3 flights up - not for the weak. Bed was comfy."
The price is AED 713
AED 1,231 total
includes taxes & fees
27 Oct - 28 Oct
Perfect location Sleeps 3
Stylish Back Bay Retreat, Steps from Prudential
Exterior

Stylish Back Bay Retreat, Steps from Prudential

8.8 out of 10, Excellent, (6)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
Stylish Back Bay Retreat, Steps from Prudential
82 Newly Renovated, Luxury Apt in Boston
Fridge, microwave, oven, stovetop

82 Newly Renovated, Luxury Apt in Boston

9.6 out of 10, Exceptional, (27)
"We had a wonderful stay at this Apartment! The place was exactly as described- clean, modern and well equipped. The location is excellent close to the metro. The host was very friendly and responsive, making check in super easy. "
The price is AED 746
AED 1,681 total
includes taxes & fees
5 Oct - 6 Oct
82 Newly Renovated, Luxury Apt in Boston
14a-Cozy and well decorated apartment in awesome Boston
Fridge, cookware/dishes/utensils

14a-Cozy and well decorated apartment in awesome Boston

2.0 star property
10.0 out of 10, Exceptional, (19)
"Amazing little home ...great shower and the most amazing host I've ever had ...thank you so much Jenny for your kindness."
The price is AED 768
AED 1,710 total
includes taxes & fees
5 Oct - 6 Oct
14a-Cozy and well decorated apartment in awesome Boston
1 Mi to Downtown: Salem Vacation Rental!
Apartment (1 Bedroom) | Interior

1 Mi to Downtown: Salem Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"very nice owner. wasnt the most comfortable bed and pillows but clean and pretty"
The price is AED 522
AED 1,184 total
includes taxes & fees
2 Nov - 3 Nov
1 Mi to Downtown: Salem Vacation Rental!
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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Top Winchester Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"One of the best hotels that I have visited. The customer experience was amazing. Each one of the staff at the hotel were helpful and courteous "
Suresh 1-night trip
Posted 4 hours ago
Seaport Hotel Boston

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 3822 hotels and accommodations including 2067 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. Onsite laundry facilities and a water park 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. Maverick Suites at 28 Fenway: Located in Boston, 7.7 mi/12.5 km away. Includes free WiFi and Smart TVs. Onsite laundry facilities and concierge services are on site. 3 bd 2 ba Unit: Located 5.2 mi/8.4 km away in Somerville. Amenities include free WiFi. Access to free parking is available on site. Apartments in Salem: It's located in Salem, 13.3 mi/21.4 km from Winchester. Includes free WiFi 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?
Explore the area and family-friendly sights such as Winter Pond, or get out into nature at a spot like Boston Common. 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.