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.
Guest favourite
Guest suite in Winchester
Warm and cozy 1st flr sweet guest suite w parking
Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits
Jan. 27 – Feb. 3
$144 CAD per night
5.0 out of 5 average rating, 95 reviews
Guest favourite
Guest suite in Burlington
Relaxing 2 Room Suite with Private Bath/Deck/Patio
Welcome to this spacious, quiet and relaxing furnished suite (private entrance own deck- patio-fire pit). It is truly in an amazing location; walking distance to Mall/Lahey Hospital & only 18 mi from Boston Logan Airport, with plenty of parking. Our place is good for professionals, students, couples, solo, families (with kids). The airbnb is attached to a main house but it's contactless (check-in/-out) with own entrance. Ideal for 2, a little tight for 3 but manageable (sofa into bed).
Aug. 27 – Sep. 3
$150 CAD per night
4.97 out of 5 average rating, 198 reviews
Guest favourite
Guest suite in Arlington
Cozy 1 bed apt Cambridge/Somerville/Arlington line
Our location is only 1.2 miles from Tuffs University and 2.4 from Harvard University. It is in the middle of North Cambridge, Somerville, and Medford. You could walk to Davis Square or to downtown Arlington and will find plenty of good restaurants and coffee places to explore. It is only 3 minutes to public transportation, bus that connects with Red line in the MBTA subway system. Our residential neighborhood is young and vibrant, and excellent point to explore Boston and surrounding towns.
Aug. 27 – Sep. 3
$266 CAD per night
4.92 out of 5 average rating, 152 reviews
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Quick stats about vacation rentals in Winchester
Total rentals | 20 properties |
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Wifi availability | 20 properties include access to wifi |
Rentals with dedicated workspaces | 10 properties have a dedicated workspace |
Family-friendly rentals | 10 properties are a good fit for families |
Total number of reviews | 900 reviews |
Nightly prices starting at | $41 CAD before taxes and fees |
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