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- 3rd Sep 2025
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48 hours in Windermere: A local’s insider guide to the ultimate Lake District Weekend at The Penn
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If you’re planning a weekend in the Lake District and searching for the best hotels in Windermere, you’ll soon realise there are plenty to choose from.
But among them all, there’s one that feels like a true hidden gem – the kind of secret you almost don’t want to share.
Welcome to The Penn Windermere.
Tucked between the leafy streets of Windermere village and nearby Bowness-on-Windermere, this ivy-clad townhouse is a luxury four-star boutique hotel that feels like a private hideaway. With chic interiors, individually designed rooms and thoughtful touches from the family who runs it, The Penn is intimate, welcoming and quietly luxurious.
Framed by rolling fells and shimmering lake views, Windermere is one of the Lake District’s most iconic destinations. You can hike to breathtaking viewpoints in the morning, sail across England’s largest lake by afternoon and settle into a cosy pub at night.
Whatever your plans, The Penn is the kind of place you’ll want to return to again and again. We caught up with family owners Harry, Madeleine, and Juliette to get their insider recommendations on how to make the most of your stay…
DAY ONE: ARRIVAL, LAKESIDE STROLLS AND PIZZA IN BOWNESS
That first drive into the Windermere never fails to impress – rolling fells, stone cottages, drystone walls and glimpses of shimmery lake water. Pulling up at The Penn Windermere, you’re greeted by a 19th-century townhouse draped in ivy and flowers. It’s the kind of place you almost want to keep secret.
With parking spaces right outside and fuss-free self-check-in, arrival is simple. Each of the 14 rooms has its own personality with six types of suites to choose from…
THE PERSONAL TOUCHES
What sets The Penn apart are the little details. You’ll receive a welcome book full of local recommendations. And if you’re celebrating a special occasion, let them know, you may find a bottle of fizz and a handwritten note waiting in your room. There’s also a complimentary sweet treat from The Toffee Shop in Penrith, plus the radio playing softly – instantly creating a home-away-from-home feel.
Need more tips during your stay? The Penn team are just a text or phone call away, always happy to help within the hour.
Once you’ve settled in, take a 25-minute stroll (or quick £3 bus ride) down to Bowness-on-Windermere. You’ll love the waterfront atmosphere – boats bobbing gently while visitors soak up the lakeside air. For dinner, locals love Base Pizza (walk-ins only, so go early). Afterwards, order a cocktail at The Fizzy Tarté or sip a glass of wine at Lake View Garden Bar, perfect for people-watching as the sun sets.
Head back to The Penn for a cosy night wrapped in soft sheets on your comfy king-sized bed, with the gentle sounds of Windermere village outside your window.
DAY TWO: HIKING, BRUNCH AND SUNSET ON THE LAKE
Start the morning with a Lakeland classic: Orrest Head. Just 20 minutes from The Penn, this short walk offers one of the most iconic views in the Lakes – Windermere stretching below with peaks rolling into the distance. Want more of a challenge? Try Wansfell Pike from Troutbeck – a three-hour loop with sweeping panoramas.
After your hike, brunch is essential – you’ve earned it. Head to Homeground Coffee + Kitchen in Windermere, known for artisan coffee and standout dishes like shakshuka, the biggest French toast you’ve seen and fluffy pancakes.
In the afternoon, it’s your chance to get out on the water. From Bowness Pier, you can join a relaxed Windermere Lake Cruise or book something more adventurous with Wake on the Bay – from wakesurfing to private yacht charters. However you do it, seeing Windermere from the lake is unforgettable.
For dinner, the Lake District’s country pubs shine. The Hare & Hounds at Bowland Bridge is a cosy choice for hearty Cumbrian cuisine, while The Brown Horse Inn at Winster offers roaring fires and traditional pub classics. If you’d rather stay close to home, The Tilly Bar & Kitchen in Windermere serves pizzas, burgers and cocktails just a short walk from The Penn.
Round off the night by working your way through the cocktail menu at Brown Sugar, then head to The Crafty Baa Windermere – a quirky little bar full of character and craft ales (don’t miss the toffee apple beer).
Head back to The Penn, sink into the bathtub or unwind with luxury handmade keratin hair and bath products from Pure Lakes – the perfect end to a day in the Lakes.
DAY THREE: COFFEE, ANTIQUES AND FAREWELL FELL VIEWS
Check-out at The Penn is at 10am, giving your plenty of time to explore Windermere before heading home. Start with speciality coffee and toasted sandwiches at Toast Windermere, ideal for a quick breakfast.
If you’re in no rush, drive to Chesters by the River near Skelwith Bridge. With its riverside terrace, vegetarian-friendly menu and legendary cakes, it’s a must-visit. There’s also a gentle riverside walk here – a lovely way to stretch your legs before heading home. For something a little different, stop by Yew Tree Barn in High Newton, where antiques, coffee and hearty food all come together under one roof.
WHY WE’LL BE CHOOSING THE PENN WINDERMERE OVER AND OVER AGAIN
What makes The Penn Windermere stand out among hotels in Windermere? It’s that rare blend of boutique style, prime location and genuine hospitality. Run by Harry, Madeleine, and Juliette – a family who’ve poured their love of the Lakes into every detail – The Penn feels warm, stylish and personal.
From its peaceful yet central spot, you’re just minutes from Windermere village and Bowness, with endless walks, pubs and independent shops on your doorstep. Whether you’re here for a romantic escape, a solo recharge, or a family weekend, The Penn isn’t just a place to stay – it’s the ultimate base for your own Lake District adventure which makes you feel like you’re living like a local.
Rachael Ellis
Head of Content
After gaining a first in her BA Media and Journalism degree at Northumbria University, Rachael worked at Newcastle’s leading regional newspaper with her stories being picked up in national and global newspapers. She spent two very successful years giving a voice to those communities across the North East who otherwise…
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