Winchester holiday rentals

We found 1,947 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
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Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include a garden and pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

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Explore the lakeside setting in Winchester

The wildlife and lake provide a pleasant backdrop to your holiday home in Winchester. This city is well-known for its football matches and bird watching. TD Garden and Fenway Park are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Winchester

Do you want to discover top things to see and do in the city? Venture out of your holiday home and check out everything that makes Winchester a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 adventure or just want to take in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (7.6 mi / 12.3 km)
  • Copley Square (7.7 mi / 12.4 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)
  • Back Bay Fens (7.8 mi / 12.5 km)

Travelling 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 centre. If you're unable to find a flight that fits your schedule, you could also fly into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away.

If you'd rather travel 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 holiday home accommodation in Winchester?

The most sought-after types of holiday homes in Winchester are condos. Searching for something different? Vrbo has numerous options to match our guests' requirements, so you'll see holiday 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 holiday home in Winchester?

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

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

The average price for a holiday home 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 holiday homes 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 holiday homes to book a property where your pup can lap up the good times.

What are popular home amenities in Winchester?

When it comes to home amenities that guests search for in Winchester, a garden, high-speed internet services and off-street parking options rank the highest. With Vrbo holiday 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 holiday homes 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 favourite.

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 holiday homes 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 holiday homes with WiFi in Winchester. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.

How old do you have to be to rent a holiday home in Winchester?

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

How long can I rent a holiday home in Winchester for?

How long you can book a holiday home 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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