Where to stay around Winchester, MA?

Our 2018 property listings offer a large selection of 1,457 vacation rentals near Winchester. From 958 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 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:

  • Back Bay: 521 vacation rentals
  • North End: 332 vacation rentals
  • Downtown: 633 vacation rentals
  • South End: 530 vacation rentals
  • Brookline Village: 78 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:

  • Winchester Wedgemere Station: 1,675 vacation rentals
  • Winchester Station: 1,673 vacation rentals
  • Boston Common: 1,710 vacation rentals
  • Boston-Back Bay Station: 1,710 vacation rentals
  • Fenway Park: 1,706 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 958 apartments in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos: 232 rentals available
  • Houses: 162 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 120 golf rental rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Beachfront rentals: 39 rentals
  • Ocean view rentals: 25 rentals
  • Monument view rentals: 23 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 1,455 vacation rentals with online bookable available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    The lakeside setting of Winchester is ready to explore

    The wildlife and lake provide a pleasant backdrop to your vacation home in Winchester. This city is well-known for its soccer games and bird watching. Harvard Square and USS Constitution Museum are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

    Activities and attractions in and around Winchester

    Are you hoping to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winchester a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

    • New England Aquarium (8.1 mi / 13 km)
    • Artisans Asylum (5.3 mi / 8.6 km)
    • Franklin Park Zoo (10.8 mi / 17.3 km)
    • Andover Bird Sanctuary (13.7 mi / 22 km)
    • Salem Toy Museum (13.8 mi / 22.2 km)
    • Salem Willows Park (15.2 mi / 24.4 km)

    Exploring the natural features in Winchester

    Whether you're an adventurous traveler or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Winchester. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

    • Boston Public Garden (7.8 mi / 12.6 km)
    • Boston Common (7.9 mi / 12.7 km)
    • Walden Pond (10 mi / 16.1 km)
    • Royall Park (3.3 mi / 5.4 km)
    • Logan Park (3.5 mi / 5.7 km)
    • Magoun Park (3.5 mi / 5.7 km)