Where to stay around Winchester?

Our 2019 property listings offer a large selection of 1,455 vacation rentals near Winchester. From 164 Houses to 3 Bungalows, 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: 670 vacation rentals
  • North End: 390 vacation rentals
  • Beacon Hill: 485 vacation rentals
  • Downtown: 659 vacation rentals
  • Jamaica Plain: 67 vacation rentals

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

Can I rent Houses in Winchester?

Yes, of course. HomeAway has 164 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Bungalows: 3 rentals available
  • Cabins: 3 rentals available
  • Cottages: 3 rentals available

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

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 55 vacation rentals with pool 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)