Where to stay around Winchester?

Our 2018 property listings offer a large selection of 1,496 vacation rentals near Winchester. From 955 apartments to 232 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 HomeAway.

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:

  • Back Bay: 521 vacation rentals
  • Downtown: 635 vacation rentals
  • North End: 332 vacation rentals
  • Beacon Hill: 389 vacation rentals
  • South End: 530 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Winchester?

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

  • Winchester Wedgemere Station: 1,719 vacation rentals
  • Winchester Station: 1,720 vacation rentals
  • Boston Common: 1,744 vacation rentals
  • Fenway Park: 1,741 vacation rentals
  • Boston Convention and Exhibition Center: 1,770 vacation rentals

But there are many other points of interest around Winchester listed on HomeAway 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. HomeAway has 955 apartments in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos: 232 rentals available
  • Houses: 151 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 downtown rentals in Winchester?

Absolutely, HomeAway has 278 downtown rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Golf resort rentals: 131 rentals
  • Near the ocean rentals: 87 rentals
  • Ski rentals: 81 rentals

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

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 103 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    Take in the Lakeside Beauty of Winchester

    The lake, flowers and wildlife display a scene truly unique to Winchester. This family-friendly city allures visitors with its soccer and bird watching. Top attractions in the area include Harvard Square, USS Constitution Museum and TD Garden. Whether you're planning a family vacation, friends trip or romantic retreat, consider a rental home. Many rentals come with a full kitchen and separate dining area.