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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 from...read 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 my...read 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 vs....read 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 - humorously...read more

 

Public Garden

Great place to relax in nearly any season, but it's harder to enjoy in winter :) People watch, bird watch, squirrel watch...read 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 and...read 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 was...read 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 movies...read more

 

Coolidge Corner Theatre

I LOVE this place! I've been coming here since I was 7 years old and I'm in awe of how amazing it continues to be. Hosts classic movies, current movies,...read 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 on...read more

 

SoniYoga

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 early...read 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 group...read 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 place...read more

 

The Breathing Room

Reviewing the Breathing Room is a little weird. It's like reviewing home, or your parents. The Breathing Room *is* my home away from home. I've tried all...read more

 

Freedom Trail Foundation Tours

Our tour was entertaining and very informative. Our guide, Isaiah Thomas, was very witty and knowledgeable. We hit many major spots in Boston History. I...read 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