Holiday rentals in Flagg

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Top-rated holiday rentals in Flagg

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Top guest favourite
A charming stone cottage is enclosed by a wooden gate, featuring a gravel pathway leading to the entrance. The structure showcases a pitched roof and large windows, blending harmoniously with the surrounding countryside.
Cottage
5 out of 5 average rating, 135 reviews

The Milking Parlour, 1 bedroom luxury cottage

A stunning award-winning one bed cottage, perfect for a romantic getaway. Stunning views from the living room stretch right across the Peak District; no exaggeration, you can see most of the Peak District from here. This luxury retreat is located on an upland sheep farm and offers character, charm, and convenience. Only a short walk to the village pub, close to all the main Peak District attractions. One well behaved dog allowed. Ideal retreat for honeymoon, romantic break or special occasion.

Top guest favourite
A spacious detached house is surrounded by lush greenery and landscaped grounds. The exterior features a stone facade, slate roof, and charming gardens with flowering plants. Free-roaming chickens are visible, adding a rural charm to the serene setting under a clear blue sky.
Home
5 out of 5 average rating, 245 reviews

The Stables House, Lomberdale Hall. 4 to 7 guests

Spacious detached private house, 3,000 sq ft/ 275 sq m. Own drive. 3 acres of grounds. Log burner (fuel provided) Front, back and garden doors; Entrance hall, sweeping staircase, beautiful sitting room, library stuffed with books, 3 large bedrooms (Vispring beds) plus 3 fab bathrooms with baths & separate showers - plus a single bed downstairs. Warm kitchen, utility room & larder. Antique furniture, lovely curtains. Perfect for families, couples, groups. Walking galore! 3 Pubs in the village.

Top guest favourite
The Tower emerges from a lush green landscape, surrounded by tall trees and manicured grass. The building's robust concrete structure is accented by its original window designs, reflecting the natural beauty of the outdoors in a tranquil setting.
Tower
5 out of 5 average rating, 239 reviews

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.

Top guest favourite
An aerial view showcases a traditional stone barn along with a historic residence surrounded by lush greenery. A well-maintained garden is visible, and the tranquil village landscape extends into the background. Nearby stone buildings and open fields complete the scenic view.
Barn
4.98 out of 5 average rating, 130 reviews

The Shippon at Manor House Farm

Renovated traditional barn in the picturesque village of Monyash, on the edge of the dramatic Lathkill Dale, in the very heart of the Peak District. Minutes from Bakewell and Buxton. The Shippon has 3 large double bedrooms, a flexi-room that can be used as a bedroom or TV-room depending on guest needs; two full bathrooms, a great kitchen linked to dining room, and a separate lounge with OLED TV, and Sonos speakers throughout. Courtyard and paddock gardens with seating. Parking is on-site.

Top guest favourite
A small round table is set in front of a stone cottage, adorned with a potted plant and a tea set. Two metal chairs are positioned around the table. The window above features a grid pattern with decorative items visible inside.
Cottage
4.97 out of 5 average rating, 286 reviews

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.

Guest favourite
A cozy interior of the shepherd’s hut is presented with wooden accents and a functional kitchenette. Natural light enters from a window, illuminating the spacious bed with soft linens. A bathroom area is visible in the background, featuring a freestanding bath, creating a peaceful retreat ambiance.
Shepherd’s hut
4.83 out of 5 average rating, 246 reviews

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.

Top guest favourite
The spacious room features a king-size bed with a floral duvet cover and a mirrored vanity. A round table and chair provide seating, while bi-fold doors open onto a covered decking area. The outdoor space is surrounded by lush greenery, adding a serene touch.
Guest suite
5 out of 5 average rating, 694 reviews

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.

Top guest favourite
The charming cottage exterior is enveloped in lush greenery, featuring stone walls and a vibrant green door. A well-maintained pathway leads to the entrance, bordered by a variety of colorful plants and bushes, set against a backdrop of a clear blue sky.
Cottage
4.99 out of 5 average rating, 330 reviews

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.

Guest favourite
A charming stone cottage is surrounded by lush greenery, with flowering plants in the foreground. The cottage features a welcoming entrance with a light green door and multiple windows that allow natural light to fill the interior.
Cottage
4.92 out of 5 average rating, 159 reviews

Sleeps 4 cosy cottage near Buxton & Bakewell

Rose Cottage has been sympathetically restored to create a cosy and secluded cottage, in the pretty village of Chelmorton, with fabulous outdoor space. Located between Buxton and Bakewell and with a fantastic village pub within walking distance, this is a great countryside bolthole from which to explore the Peak District. Perfect for couples or families with small children, dog friendly and cycle friendly. We can accept 2 dogs and a fee of £30.00 per dog is payable.

Top guest favourite
Barn
4.98 out of 5 average rating, 249 reviews

Curlew Cottage - Rural Cottage escape.

Curlew Cottage Rural Cottage Escape - is a detached, tastefully decorated, rural cottage situated in the White Peak area of the Peak District Located between Bakewell and Buxton Perfect space for singles and couples to chill, walk, cycle exploring nature, unwind and get away from it all What to expect Fantastic views Animal, family and farm sounds Black starry skies Changeable weather Snow in winter No public transport Slow WiFi Sketchy mobile Wildlife noises

Top guest favourite
The living area features two comfortable sofas positioned around a central wooden coffee table. A decorative console cabinet is present against the wall, accompanied by a small plant. Light enters through a nearby window, while a log burner is set within a stone hearth.
Home
4.99 out of 5 average rating, 167 reviews

White Peak Cottage

Newly renovated, this cosy yet modern cottage is located in a quiet village in the heart of the Peak District. Within walking distance of the village pub and within a short drive of beautiful Bakewell it is ideally located for you to enjoy all the Peak District has to offer. Ideally suited to couples or friends we also welcome families and allow two well behaved dogs. Check in days are Monday, Friday and Saturday, discounts on weekdays and for seven day breaks.

Top guest favourite
The green and black exterior of the converted railway goods van is highlighted by large, open doors. A tan canopy provides shade over the entrance, while a wooden chair is positioned nearby. Natural surroundings and a gravel area create a peaceful outdoor setting.
Shepherd’s hut
4.99 out of 5 average rating, 322 reviews

“The Goods Van” at Stoop Farm

Relax in total comfort, in our converted 1950s railway goods van. Once common place on farms around the Peak District this little gem is far removed from the animal shelter it once was! Fitted out to the highest quality, featuring a king sized bed, comfy sofa, kitchen, log burner and smart TV, etc. Something quite special, situated in its own secluded area, a few steps away from the magnificent views of Chrome hill and the Dove valley beyond.

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