Winchester, MA, USA

Winchester, MA, USA

We found 1,437 vacation rentals — enter your dates for availability


Find the best place to stay — Winchester

Where to stay around Winchester?

Our 2018 property listings offer a large selection of 1,437 vacation rentals near Winchester. From 893 apartments to 219 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.

Can I rent apartments in Winchester?

Yes, of course. VRBO has 893 apartments in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos: 219 rentals available
  • Houses: 202 rentals available
  • Studios: 35 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 116 golf rental rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Beachfront rentals: 42 rentals
  • Ocean view rentals: 29 rentals
  • Monument view rentals: 17 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 1,434 vacation rentals with online bookable available in Winchester. Please use our search bar to access the selection of vacation rentals available.