Winchester holiday homes

We found 106 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 5 homes and other holiday rentals in Winchester that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a hot tub. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

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  • All the privacy of home
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Find the perfect holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Winchester

Do you want to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Winchester a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Connecticut Valley Winery (8.3 mi / 13.4 km)
  • Ski Sundown (9.4 mi / 15.2 km)
  • Mohawk Mountain Ski Area (12.4 mi / 20 km)
  • Flamig Farm (13.5 mi / 21.7 km)
  • Talcott Mountain State Park (17.9 mi / 28.8 km)
  • Sunset Meadow Vineyards (11.1 mi / 17.9 km)

Exploring the natural landscape of Winchester

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Winchester is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Highland Lake (2.6 mi / 4.3 km)
  • Haystack Mountain State Park (6.9 mi / 11.1 km)
  • Satan's Kingdom State Recreation Area (9.5 mi / 15.4 km)
  • Woodridge Lake (11.5 mi / 18.6 km)
  • Mohawk Mountain State Forest (12.2 mi / 19.6 km)
  • Litchfield Town Green (13.6 mi / 22 km)

How to get to and around Winchester

Fly into Hartford, CT (BDL-Bradley Intl.), the closest airport, located 21.9 mi (35.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Winchester?

Houses are the most popular kind of holiday home in Winchester, according to our data. Even if you have a different idea about what you want, Bookabach has holiday homes in a variety of sizes and shapes. Explore our options to find your ideal fit.

How much does it cost to rent a holiday home in Winchester?

Several factors influence how much you'll pay for a holiday home in Winchester, like the season, type of property and length of stay. But, all our holiday homes have something in common — amazing value. Simply enter your travel dates to find your perfect fit.

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 will depend on when you'll be there and the type and size of property you want. You can find prices easily and quickly on Bookabach by entering your dates of travel. Then use the handy filter tool to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.

Are there pet-friendly holiday homes in Winchester?

Happily, yes. You'll find eight holiday homes that welcome pets in Winchester on Bookabach. Our cuddly best friends also deserve a little time out, so simply use our search function for pet-friendly holiday homes to book a perfect pad where Rover can join the fun.

What are popular home amenities in Winchester?

Some of the most popular home amenities people are looking for in Winchester include a lake view, nearby museums and a nearby waterfront. Whether you're travelling with family, your besties or even pets, Bookabach holiday homes have the best amenities for making new memories with the people who matter most.

Are there large group holiday homes in Winchester?

With six Winchester properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal get-together or a birthday party, we'll help you book the ideal space for the occasion.

Are there holiday homes in Winchester that welcome kids?

With eight family-friendly holiday properties available in Winchester, now is a superb time to introduce the kids to the joys of travel. Simply click on our "Properties good for families" filter box to search for stays that come with conveniences ideal for holidaying families, such as living rooms, patios, hot tubs and bunk beds.

What are the top attractions for families in Winchester?

Keep the kids amused at these leading family-friendly attractions in Winchester:

  • Winchester Historical Society
  • Laurel Lanes
  • Highland Lake

Can I find two-bedroom holiday homes in Winchester?

Gather your nearest and dearest and experience complete comfort and privacy in one of the three two-bedroom holiday homes Winchester has to offer.

Are there holiday homes with WiFi in Winchester?

You can choose from six holiday homes with WiFi in Winchester. If you'd like to disconnect from the world while on holiday, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Bookabach.

How can I find holiday homes with air conditioning in Winchester?

Pick from eight Bookabach holiday homes with air conditioning in Winchester offering that cool, cool breeze and extra touch of comfort. Simply enter your travel dates and then make use of our filters to look for stays with air conditioning.

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

Age restrictions can differ between properties on Bookabach, so check the rules of the holiday home in Winchester you want. But in general, it's 16, 18 or 21.

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