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Apartments in Winchester

The Sailor’s Retreat – Cozy Historic Apartment Rental in Marblehead, MA

10.0 out of 10, Exceptional, (7)
"Sailor's Retreat was the perfect place for our weekend trip to Marblehead! The stay was so cozy and it was stocked with all the necessities! The town is so sweet and lovely! It is only a quick drive to Salem, and Boston day trips! "
The Sailor’s Retreat – Cozy Historic Apartment Rental in Marblehead, MA

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"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
25 Jun - 26 Jun
Cozy Seaside studio in charming Marblehead with AC, WiFi. Short walk to downtown

Lovely 1.5 bedroom in the great historic town

9.6 out of 10, Exceptional, (37)
"Very cute apartment, Tina was a great host and responded immediately to any questions. She was wonderful! Family very much enjoyed their stay and will be back again."
The price is AED 397
AED 882 total
includes taxes & fees
1 Jul - 2 Jul
Lovely 1.5 bedroom in the great historic town

Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!

9.2 out of 10, Wonderful, (9)
"Absolutely loved everything about this gem of a find. Centrally located and very quiet. Beautifully decorated - real zen-like vibe. Thoroughly enjoyed our stay!"
The price is AED 517
AED 1,259 total
includes taxes & fees
2 Jul - 3 Jul
Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!

Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

9.8 out of 10, Exceptional, (16)
"The place was lovely. And decorated beautifully. "
The price is AED 1,003
AED 1,875 total
includes taxes & fees
20 Jun - 21 Jun
Artful Escape • Minutes to Salem, Beach and Train to Boston • Private Parking

Down Town Salem brand-new 1bdr apt

10.0 out of 10, Exceptional, (20)
"Such a cute place and a close walk to almost everything. Everything we could have wanted. Definitely would stay again. "
The price is AED 661
AED 1,149 total
includes taxes & fees
26 Jun - 27 Jun
Down Town Salem brand-new 1bdr apt

Re-listed: Adorable Condo Beverly - Salem - Halloween

9.8 out of 10, Exceptional, (14)
"Small, clean ,quiet , great location Work definitely rent again"
The price is AED 416
AED 1,003 total
includes taxes & fees
30 Jun - 1 Jul
Re-listed: Adorable Condo Beverly - Salem - Halloween

Salem Spacious Second Floor 3-4BR!

9.0 out of 10, Wonderful, (8)
"Enjoyed our stay"
The price is AED 1,256
AED 1,714 total
includes taxes & fees
22 Jun - 23 Jun
Salem Spacious Second Floor 3-4BR!

Apartments in Salem

3.0 star property
8.0 out of 10, Very Good, (45)
"This was a great spacious place! It was a great location to all the attractions and restaurants! We walked everywhere! "
Apartments in Salem

*Omi's Downtown Salem Escape |Halloween+HocusPocus

10.0 out of 10, Exceptional, (22)
"Easy access to downtown Salem. Wonderfully beautiful location."
The price is AED 518
AED 1,104 total
includes taxes & fees
23 Jun - 24 Jun
*Omi's Downtown Salem Escape |Halloween+HocusPocus

1 Mi to Downtown: Salem Vacation Rental!

3.0 star property
The price is AED 591
AED 1,257 total
includes taxes & fees
6 Jul - 7 Jul
1 Mi to Downtown: Salem Vacation Rental!

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

3.0 star property
9.0 out of 10, Wonderful, (2)
"Very nice place to stay. Super cute and clean. So many extras. Unfortunately not ideal for my tall husband. The shower was a bit small for his size but just right for me. The roses in the yard smelled great. Thanks for a great stay. "
The price is AED 547
AED 1,106 total
includes taxes & fees
30 Jun - 1 Jul
1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

9.8 out of 10, Exceptional, (18)
"The owner was in communication the entire stay and made sure everything ran smoothly."
The price is AED 441
AED 1,128 total
includes taxes & fees
2 Jul - 3 Jul
1 Mi to Downtown Salem: Studio w/ Fire Pit Access

1 Mi to Downtown: Salem Vacation Rental!

9.6 out of 10, Exceptional, (23)
"Clean, great location"
The price is AED 1,069
AED 2,137 total
includes taxes & fees
12 Jul - 13 Jul
1 Mi to Downtown: Salem Vacation Rental!

555-2 - 6BR - Quincy Spacious Apt near Perry Beach

9.8 out of 10, Exceptional, (25)
"House was great plenty of room for all of us would definitely stay again!"
The price is AED 1,722
AED 3,105 total
includes taxes & fees
22 Jun - 23 Jun
555-2 - 6BR - Quincy Spacious Apt near Perry Beach

Gorgeous Oceanfront Penthouse

10.0 out of 10, Exceptional, (86)
"Very nice place, beautiful views and great location, especially if you like to walk along the beach. "
The price is AED 1,010
AED 1,776 total
includes taxes & fees
25 Jun - 26 Jun
Gorgeous Oceanfront Penthouse

NEW 1803 Historic Apartment in Heart of Salem•Steps to Haunted Happenings!

2.0 star property
8.8 out of 10, Excellent, (3)
"Great spot"
The price is AED 745
AED 1,435 total
includes taxes & fees
2 Jul - 3 Jul
NEW 1803 Historic Apartment in Heart of Salem•Steps to Haunted Happenings!

NEW! Family-Friendly Getaway < 1 Mi to Dtwn Salem!

3.5 star property
NEW! Family-Friendly Getaway < 1 Mi to Dtwn Salem!

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

10.0 out of 10, Exceptional, (42)
"This was a great stay! Frank was super nice and helpful, the recommendations he made were perfect for what we wanted. The house is so cute and has great character, comfy beds and plenty of space for the 5 adults we had. "
The price is AED 657
AED 1,305 total
includes taxes & fees
23 Jun - 24 Jun
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Luxury and Modern Apt near Mall/ Hospital

10.0 out of 10, Exceptional, (27)
"Really enjoyed our stay. Perfect location, clean, bright and modern. Would definitely stay again."
The price is AED 918
AED 1,760 total
includes taxes & fees
25 Jun - 26 Jun
Luxury and Modern Apt near Mall/ Hospital
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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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 3723 hotels and accommodations including 2057 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. Great Apartment on River/ Harvard Square two blocks: It's located in Cambridge, 5.4 mi/8.7 km away. The Chester Hotel: 8.3 mi/13.4 km away in Boston. Free WiFi, premium mattresses, and Smart TVs are included. 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.