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Vacation Rentals in Winchester, Massachusetts

about Winchester

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Winchester, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Winchester are added and updated every week!

Compared to hotels, Winchester vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Winchester, Massachusetts Vacation Rentals and Tourism

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Winchester things to do


Boston Derby Dames

$12 Ticket + $5 Drink + $2 Food + $1 Tip = $20 One twenty dollar bill for 4 hours of: (a) hanging with the widest slice of society from old men who more


Somerville Theatre

Do you know what it's like to watch Wolf of Wall Street with 2 beers in one hand and a beautiful lady's thigh in the other? I do, thanks to the more


Achieve Fitness

I have now been at Achieve Fitness for just over a year so I figured it was time for a little update. I cannot say enough about the gym. The more


Public Garden

While it's not my official 1,000th review, this update owns just as much a place in the ol' ticker, as the Public Garden is the spot where the lady and more


Brattle Theatre

Charmed and charming, you are Brattle Theatre. Thank you for being a cozy, hip staple in HSQ for independent film and culture. So you know, Yelpers: more


Cambridge Center Roof Garden

This is my first time visiting the park. They do a great job if blocking out the sounds of the city and creating a calming peaceful greenery. However, I more


Coolidge Corner Theatre

I don't think I am smart enough to enjoy all of the cool that this place is. CCT tends to play limited release indie films and foreign flicks. Every now more


Urban AdvenTours

A fun way to see Boston. I have a bad back so would not survive the all the walking to see all the sights. Boston drivers can be aggressive jerks, more


The Comedy Studio

Been here many times. I liked 80% of the comedy, which is pretty huge relative to the variety you get and how easily I get bored. I like the General Gau' more


American Repertory Theater

The A.R.T. is fantastic and is a gem in the Cambridge/Boston community. They push the boundaries of theater and produce high-quality work. I've more


The Esplanade

I enjoy the views as I run by, son sits happy in the jogger also. Their is always so much to see. The grass is very clean. He gets out and tries to keep more



Absolutely charming studio with a very non-commercial, real "yoga" feel to it. Great pricing, great schedule, some amazing instructors, variety of more


The Training Room 1

I started coming here for training after my trainer Regan left Healthworks. I'm still here a year later. The workouts with Regan now are so much more


Redline Fight Sports

I've been to Redline a number of times. Once years ago when initially searching for an MMA gym and again recently with a groupon, where I've attended more


Freedom Trail Foundation Tours

I'm a self proclaimed American history fanatic. I grew up watching Liberty's Kids on TV, read through an entire book series called "A History of Us" when more

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Upscale 5 BR Boston Home - April Boston Marathon & July/Aug Family Vaca
Winchester House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $475 - $950 /nt
    $4,200 - $4,900 /wk

10 reviews write a review

Luxurious House. 7 miles to Boston, 1000 FT to train.
Winchester House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths 2
  • rates (USD) $390 /nt
    $2,450 /wk

19 reviews write a review