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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


Achieve Fitness

I joined Achieve about a year ago and have seen amazing changes, not only in my fitness level, but also in my overall health and attitude. I have gone more


Urban AdvenTours

I rented Urban AdvenTours bike through using my Go Boston Card. The staff was very friendly and easy-going, enough to throw jokes around (when returning more


Boston Derby Dames

I didn't really expect anything so was incredibly surprised by HOW MUCH FUN IT IS to go watch the Derby Dames! I saw the expo of Boston B Party more


Somerville Theatre

PRO: Its cheap-ish for its location. CON: The popcorn. I swear instead of butter they use water... which is as disgusting as it sounds - more


be. in Union Yoga

Today was my first class at Union Yoga and it was perfect! I have recently moved to the area and have been away from a regular yoga practice for more


Public Garden

Much as New York has their garden, this is Boston's drop of natural serenity situated in between the towering display of urban prowess. On the menu more


American Repertory Theater

I really like this theater because you have a great view of the stage no matter where you sit. It's a smaller theater, so definitely more quaint 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


Brattle Theatre

The Brattle is an awesome venue for classic, cult and indie movies, as well as new book events sponsored by the Harvard Book Store. The schedule of more


Coolidge Corner Theatre

Awesome theater. It comes in just behind the Somerville Theater for me as far as alternative theaters go, but it's still solid, hence the 5 stars. more


The Comedy Studio

Neat set-up of comedy most nights and magic show other nights. A friend invited me to check it out, and we ended up going to the magic show more



Past Sunday morning was the first time I took Soni's class at the Cambridge studio (I'm fast becoming a regular at the Burlington one). We were there more


The Training Room 1

I have been coming to the Training Room for about a year and a half. I've taken Spin classes, 50/50, Bells & Wheels, Yoga, and even done some small more


Christopher Columbus Waterfront Park

Every now and then you will find me grasping for the right words to describe a place I've recently visited. Christopher Columbus Waterfront Park is a more


Freedom Trail Foundation Tours

We were lucky enough to have a tour with the legendary Jeremiah Poope (like a lot of other Yelpers). He definitely knew his audience and kept it fun for more

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Luxurious House. 7 miles/14 minute drive 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 - $890 /nt
    $2,450 /wk

24 reviews write a review