A five bedroom holiday cottage in Dorset is made for memorable group getaways, where space, comfort and togetherness matter most. Perfect for extended families, large groups of friends or multi-generational holidays, these impressive properties offer room for everyone to relax, celebrate and reconnect.
Often set in standout coastal or countryside locations, our five bedroom cottages provide generous living areas, large dining spaces and plenty of bedrooms for privacy and comfort. Whether you’re planning a special occasion, a festive break or a long-awaited reunion, these large cottages offer a truly special way to experience Dorset.
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Church Knowle, Nr Corfe Castle 
4.9/5
Church Knowle
4.8/5
Corfe Castle
5/5
There’s something magical about spending Christmas together in Dorset, and a five bedroom cottage gives everyone the space to enjoy it properly. Picture festive walks along the coast, cosy evenings by the fire, and long Christmas dinners enjoyed around a large table with all your favourite people.
Many of our larger cottages are ideal for festive stays, offering spacious kitchens for cooking, comfortable lounges for relaxing, and room for everyone to stay under one roof without feeling on top of one another. Explore our hand-picked Christmas holiday cottages in Dorset.
If you’re looking to ring in the New Year with friends or family, a five bedroom holiday cottage in Dorset makes the perfect base. With space for celebratory meals, games nights and relaxed mornings afterwards, these cottages are ideal for welcoming the year ahead together.
Dorset’s quieter winter coastline, peaceful countryside walks and welcoming local pubs provide a wonderful backdrop for a New Year escape, while a large cottage ensures you can celebrate in comfort and privacy. See more options in our collection of New Year holiday cottages in Dorset.
Beyond the festive season, five bedroom cottages are a fantastic choice for milestone birthdays, anniversaries, reunions and group holidays where space is key. With ample room for socialising and unwinding, these properties allow everyone to holiday at their own pace.
Many also benefit from large gardens, multiple bathrooms and flexible layouts, making them well suited to longer stays and groups with varying needs. Looking for even more group-friendly options? Browse our full range of large holiday cottages in Dorset.
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