Photo by Donny Campos

Winchester holiday homes

We found 292 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Take in the lakeside beauty of Winchester

The lake and forests provide a pleasant backdrop to your holiday home in Winchester. This city is relaxing and scenic, recognised for its canoeing, boating and kayaking. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Winchester

Are you searching for top things to see and do in the city? Venture out of your holiday home and experience everything that makes Winchester a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Northfield Mountain Recreation Center (12 mi / 19.3 km)
  • Brattleboro Country Club (12.2 mi / 19.6 km)
  • Brentwood Golf Course (14.9 mi / 23.9 km)
  • Monadnock State Park (15.8 mi / 25.4 km)
  • Shattuck Golf Course (16.4 mi / 26.5 km)
  • Friendly Farm (17.6 mi / 28.3 km)

Exploring the natural features in Winchester

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Winchester is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Madame Sherri Forest (9.3 mi / 15 km)
  • Madame Sherris Castle Ruins (9.4 mi / 15.1 km)
  • Chesterfield Gorge Natural Area (9.8 mi / 15.8 km)
  • Spofford Lake (10 mi / 16.1 km)
  • Brattleboro Common (10.7 mi / 17.2 km)
  • Laurel Lake (11.9 mi / 19.2 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Winchester?
Based on our data, apartments are the most in-demand property type in Winchester. But as you know, everyone’s idea of the perfect trip can vary. Bookabach has holiday homes with every shape, size and budget in mind, so you’re sure to find the perfect fit.
How much does it cost to rent a holiday home in Winchester?
Property type, length of stay and time of year are some of the conditions that can affect the price of a holiday home. Simply click on your dates of travel to find your dream escape. From cosy chalets to expansive villas, all Bookabach holiday homes offer terrific value.
How much does it cost to rent a beach house in Winchester?
The average price for a holiday home near the beach in Winchester will depend on when you’re going and the size and style of property you’re searching for. Find prices easily and quickly on Bookabach by entering your preferred travel dates. Then use the handy filter tool to pick the number of bedrooms and amenities that you need, like WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Winchester?
Yes. There are. You’ll have your pick of seven holiday homes that allow pets in Winchester. Plenty of our pet-friendly holiday homes even have space outdoors for your fur baby to run around in, special dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find your pawfect digs on Bookabach.
What are popular home amenities in Winchester?
The most popular home amenities people look for in Winchester are a firepit, a water view and nearby museums. Whether you’re going on holiday with family, friends or even pets, Bookabach holiday homes come with the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday homes in Winchester?
With four Winchester properties that can sleep five or more people, you can bring a few extra buddies or family members along. Whether you’re planning a casual get-together or a celebratory event, Bookabach will help you book a comfy space to match the occasion.
Are there holiday homes in Winchester that welcome kids?
Winchester has seven family-friendly holiday homes. And finding a stay that welcomes kids is easy with Bookabach’s “Properties good for families” filter. On top of having the whole place to yourselves, you’ll enjoy access to perks and amenities such as multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Winchester?
There are plenty of cool things to see and do with the family in Winchester, such as:

  • Birch Point
  • Pisgah State Park
  • Little Monadnock Mountain

Are there one-bedroom holiday homes in Winchester?
Winchester has two one-bedroom homes on offer. Often positioned in prime areas thanks to their compact size, a one-bedroom holiday property is great if you’re getting away with a friend or your partner. And with plenty of home comforts like kitchens and more privacy than a standard hotel, you’ll be able to chill out while enjoying this amazing destination.
Can I find two-bedroom holiday homes in Winchester?
Gather your family and enjoy total privacy and comfort in one of the five two-bedroom holiday homes Winchester has to offer.
Are there holiday homes with WiFi in Winchester?
Whether you’d like to keep up to date with the news, check emails or post a pic to social media, there are five holiday homes with WiFi in Winchester. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Winchester?
You’ll have a choice of seven holiday homes with air conditioning in Winchester providing that gentle, cool breeze and extra touch of comfort. Just enter your chosen travel dates and then take advantage of our filters to help you locate properties 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 be sure to look at the rules of the holiday home in Winchester you want to book. But usually, it’s 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
How long you can rent a holiday home in Winchester differs according to the property. Simply enter your preferred travel dates to look at a list of options offering extended stays. With loads of amenities like air conditioning and laundries, as well as some offering weekly or monthly discounts, you’re sure to get a terrific place to call your home away from home in Winchester.

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