Holiday rentals in Flagg

Modern bungalow with two bedrooms: king and double

Modern detached bungalow with king and double bedrooms, set in a quiet street just a 10-minute flat walk to the heart of Bakewell. The property offers a spacious lounge and conservatory looking out onto a mature garden, a well-equipped kitchen and ample driveway parking. An ideal base for exploring the Peak District, with Chatsworth House, Haddon Hall, and scenic country walks. Bakewell offers a range of restaurants, cafés, traditional pubs, independent shops, supermarkets and weekly market.

The Tower

The Tower is the perfect romantic high-end getaway for couples who want to get away from it all in a secluded location and fancy just something different. The Tower has recently been converted for use as a holiday let which was previously an unused ancillary building adjacent to The Water Works, an old water treatment plant near Bolsover, converted to domestic use in 2002 and featured on the Channel 4 programme Grand Designs. Available for single night stays. Discounts on 3+ nights bookings.

The Carriage at The Old Station

Step back in time with our lovingly restored 1895 GWR carriage, one of few situated at a Victorian Station. Enjoy a beautifully furnished living space, bathroom, kitchenette, and a comfy bed ensuring a restful night's sleep. Located in Saddleworth, renowned for its scenic walking routes and picturesque villages. Nearby, you'll find dining, drinking, and activities: including the world record-holding Old Bell Inn gin emporium. Book today to experience this unique, charming historical hideaway.

Heaven View Saddleworth

✨ Luxury Lodge for Two | Private Hot Tub | Incredible Views ✨ Escape the everyday in this exclusive lodge designed for those seeking relaxation and a little fun. Enjoy spectacular views of the Saddleworth Valley from your private hot tub, challenge each other on the pool table and the arcade machine. With private parking, scenic countryside walks from the doorstep, and a village pub close by, it's the perfect setting for a romantic getaway, anniversary, or peaceful break in the countryside.

Millstone Cottage - Cosy Peak District Cottage

This semi detached cosy cottage in the quiet village of Taddington, is perfect for small families who would like to immerse themselves in the beauty of the Peak District National Park . Located mid way between Buxton and Bakewell, this cottage makes a perfect base for which to explore the two towns and surrounding areas. There are many excellent picturesque places to visit, from the doorstep, nearby Monsal Dale and the famous trail, Millers Dale and Chee Dale only a short walk away.

Beautiful, private Shepherd's hut overlooking lake

Escape to our secluded shepherd’s hut overlooking a peaceful reservoir. This charming hideaway offers total privacy and stunning water views. Unwind in your own private log-fired Scandinavian hot tub, perfect for stargazing or relaxing after a day in nature. Inside, enjoy cozy comforts and rustic charm. Ideal for couples or solo travelers seeking tranquility and a break from the everyday. A true off-grid retreat. Please feel free to message us and enquire for more information.

Self contained annex - Peak District riverside

A private, self-contained, en-suite annex, next to the River Wye, in a tranquil setting. Direct access to covered decking area & shared garden so you can enjoy the water, wildlife and countryside. Food prep area with fridge, microwave, sink, kettle & toaster. Plenty of walks from the doorstep, cycle routes and climbing opportunities. Perfectly located to explore the Peak District. Car strongly recommended. The annexe is attached to our family home, but has its own entrance.

Cosy Grade ll listed cottage Central Peak District

Nestled in the picturesque village of Monyash, Mereview a Grade II listed stone cottage offers the perfect escape for couples or solo adventurers seeking peace, character, and countryside charm. Thoughtfully restored and beautifully presented, this historic home blends timeless elegance with modern comfort. Whether you’re walking the limestone dales, visiting nearby Bakewell or Chatsworth House, or simply curling up with a book by the fire, this cottage is a serene base.

Leaping Hare Barn - Rural Barn escape

Leaping Hare Barn is a rural, rustic semi off grid Barn situated between Bakewell and Buxton. A perfect space for single guests and couples to chill, walk, cycle, find peace, explore nature, unwind and get away from it all What to expect Fantastic views Animal, family and farm sounds Flies & bugs Starry skies Changeable weather Snow in winter No public transport No local amenities (shops/pubs) Slow or no WiFi Sketchy mobile signal - EE only Wildlife noises

Air conditioned Woodcutters ~ Romantic Retreat

✨ Romantic Air-Conditioned Cabin with Whirlpool Bath & Couples Spa 💖 Escape to Woodcutters Cabin — a luxury hideaway for two in the heart of the Peak District. Enjoy your private Japanese whirlpool bath with mood lighting, a plush super-king bed, and a secret shower-room door. Treat yourselves to candle-lit couples massages in our tranquil treatment room. A peaceful, baby, child-free, pet-free retreat made for romance and total relaxation.

Beautiful cosy cottage by a babbling brook

Wonderfully restored 350 year old country cottage in the picturesque hamlet of Hollinsclough. Breathtaking views of the Peak National Park, nestled under the stunning Chrome and Parkhouse hills. Ample private parking for 3 cars. Cosy log fire and a comfortable kitchen, dining & living area. Friendly and knowledgable hosts who can give great local advice including walking and cycling routes and places to visit and dine out.

Padley. A traditional shepherds hut on a farm.

Set deep within the heart of the beautiful Peak District on a working farm our traditional hand-crafted Shepherds hut is has everything for the perfect getaway. Whilst enjoying the romantic location with stunning panoramic views towards Lathkill Dale Padley provides the perfect base for exploring the peak District by offering some of the finest walks and cycle routes the Peak District has to offer straight from the door.