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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Rental unit in Woburn
Freshly renovated in 2020. Featuring two bedrooms with king-sized beds. In-unit laundry, central AC, and off-street parking. Sparkling new kitchen with everything you need to make a meal. Less than a five-minute walk to Woburn center. Steps away from grocery stores, coffee shops, restaurants, cafes and pharmacies. Less than a 5-minute drive to route 128, Middlesex Superior Court, and the Woburn TradeCenter. Just a five-minute drive to routes 93 and 120, and just 20 minutes to downtown Boston.
$88 per night
Private room in Medford
Bedroom in Cozy 1st Floor Tufts /Green Line Train
A very cozy Queen Size bedroom with desk located 2 minutes from Tuft University and Green Line Bus LIne. The unit has a shared bathroom. Wifi, Coffee, Smart TV with Netflix provided. The unit was recently renovated December 2021. Short walk to 3 bus lines that go to Boston, Harvard Square and Davis Square. Walking distance to restaurants and shops. You can drive to Boston, Encore Casino or Assembly Row Shopping in 10 minutes. Owner does not live on property.
$70 per night
Rental unit in Woburn
Charming-spacious-private 1BR conveniently located
This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy city adventures, north shore excursions, fall leaf peeping, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure.
$130 per night

Stay near Winchester's top sights

Photo of Whole Foods Market
Whole Foods Market150 locals recommend
Photo of Black Horse Tavern
Black Horse Tavern5 locals recommend
Photo of Lucia Ristorante / Winchester
Lucia Ristorante / Winchester3 locals recommend
Photo of China Sky
China Sky4 locals recommend
Photo of D'Agostino's Delicatessen
D'Agostino's Delicatessen5 locals recommend
Photo of Whipple Hill
Whipple Hill3 locals recommend

Other great vacation rentals in Winchester

Home in Medford
Couples Retreat - Charming Colonial Home
$125 per night
Guest suite in Melrose
Guest Suite with separate entrance
$87 per night
Guest suite in Woburn
Relaxing and Comfortable Home Away From Home
$100 per night
Private room in Waltham
#16 Extra Large Room with Private Bathroom
$67 per night
Private room in Medford
Cozy bedr. close to TUFTS, Harvard, MIT #1
$60 per night
Private room in Belmont
Close To Harvard MIT BC Bentley Northeastern 2
$49 per night
Home in Medford
Artsy Guest Suite close to Harvard & Tufts!
$110 per night
Private room in Arlington
@1闪闪 w/sunroom/private bathroom/ Tufts Davis Sq.
$102 per night
Private room in Stoneham
Queen Bed - Boston - RM 2
$52 per night
Private room in Waltham
#14 Super Stylish for Room 9 min to Brandeis Uni!
$47 per night
Private room in Arlington
Next to Cambridge,close to T, the 2nd of 4 rooms
$45 per night
Rental unit in Waltham
Cozy Private Studio Unit w/ Laundry and Parking!
$86 per night