Winchester vacation rentals

We found 1,952 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from vacation rentals in Winchester to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a fireplace. What you'll find is a rental to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Explore the lakeside setting in Winchester

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. TD Garden and Fenway Park are just a couple of the must-sees in the area. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Winchester

Are you hoping to discover top things to see and do during your stay? Venture out of your cozy vacation rental and check out everything that makes Winchester a fun place to get away. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Encore Boston Harbor (5.3 mi / 8.6 km)
  • New England Aquarium (7.8 mi / 12.6 km)
  • Boston Marathon Finish Line (7.7 mi / 12.4 km)
  • Harpoon Brewery (8.9 mi / 14.4 km)
  • Samuel Adams Brewery (9.7 mi / 15.6 km)
  • Franklin Park Zoo (10.4 mi / 16.8 km)

Exploring the natural landscape of Winchester

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Winchester is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Boston Common (7.6 mi / 12.3 km)
  • Copley Square (7.7 mi / 12.4 km)
  • Boston National Historical Park (6.8 mi / 11 km)
  • Charles River Esplanade (7.2 mi / 11.7 km)
  • Commonwealth Avenue Mall (7.5 mi / 12.1 km)
  • Boston Public Garden (7.6 mi / 12.3 km)

Traveling to and around Winchester

Fly into Bedford, MA (BED-Laurence G. Hanscom Field), the closest airport, located 7.7 mi (12.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away.

If you're traveling by train, make your way to Winchester Station or Winchester Wedgemere Station to see more of the city.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Winchester?

The most sought-after types of vacation rentals in Winchester are condos. Searching for something different? Vrbo has numerous options to match our guests' requirements, so you'll see vacation properties in loads of sizes and shapes. The perfect fit is ready and waiting for you — grab yours today.

How much does it cost to rent a vacation rental in Winchester?

Property type, season and length of stay are some of the things that can affect the price of a vacation home. Simply enter your dates of travel to find your ideal fit. From comfy cabins to plush villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Winchester?

The average price for a vacation rental close to the beach in Winchester depends on when you're going and the type and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your destination and preferred travel dates. Then use the handy filters to select the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Winchester?

Good news. There are. You'll find two stays that allow pets in Winchester on Vrbo. Our furry companions also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to book a property where your pup can lap up the good times.

What are popular rental amenities in Winchester?

When it comes to rental amenities that guests search for in Winchester, a garden, high-speed internet services and off-street parking options rank the highest. With Vrbo vacation homes, you'll have options to suit your style and taste, whether you're on a trip with relatives, friends or even pets.

Are there vacation rentals in Winchester that welcome kids?

Bring the entire group together for the adventure of a lifetime in Winchester at one of our two family-friendly properties. Lots of these stays provide amenities that are ideally suited to trips with the little ones, like full kitchens, extra bedrooms and private pools. Simply click on the "Properties good for families" filter and select your favorite.

What are the top attractions for families in Winchester?

Keep the kids busy at these popular family-friendly attractions in Winchester:

  • New England Aquarium
  • Museum of Science
  • Revere Beach

Are there vacation rentals with WiFi in Winchester?

Whether you'd like to keep up with the latest news, write a few emails or post a pic to social media, there are two vacation homes with WiFi in Winchester. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

How old do you have to be to rent a vacation rental in Winchester?

The minimum age requirements can vary across properties on Vrbo, so double-check the rules of the vacation home in Winchester you want to book. But normally, it's 16, 18 or 21.

How long can I rent a vacation rental in Winchester for?

How long you can book a vacation rental in Winchester is up to the property. Simply enter your desired dates to look at a list of options offering extended stays. With tons of creature comforts such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Winchester.

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