Find the best place to stay — Winchester

Where to stay around Winchester, MA?

Our 2018 property listings offer a large selection of 1,463 vacation rentals near Winchester. From 960 apartments to 206 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winchester for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Winchester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winchester:

  • North End: 335 vacation rentals
  • Dorchester: 132 vacation rentals
  • Fenway/Kenmore: 420 vacation rentals
  • South Boston: 457 vacation rentals
  • Commonwealth: 131 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Winchester?

VRBO offers a large selection of vacation rentals near lovely places in Winchester. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Jackson Homestead and Museum: 1,661 vacation rentals
  • East Boston Memorial Stadium: 1,796 vacation rentals
  • Mapparium: 1,755 vacation rentals
  • Fenway Park: 1,768 vacation rentals
  • Boston University: 1,758 vacation rentals

But there are many other points of interest around Winchester listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent apartments in Winchester?

Yes, of course. VRBO has 960 apartments in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos: 206 rentals available
  • Houses: 156 rentals available
  • Studios: 33 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including townhomes and more.

Can I rent golf rental rentals in Winchester?

Absolutely, VRBO has 120 golf rental rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Beachfront rentals: 40 rentals
  • Ocean view rentals: 25 rentals
  • Monument view rentals: 19 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Winchester?

Yes, you can select your prefered vacation rental with online bookable among our 1,461 vacation rentals with online bookable available in Winchester. Please use our search bar to access the selection of vacation rentals available.