Vacation rentals in Flagg

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Top-rated vacation rentals in Flagg

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Top guest favorite

Cottage in Monyash

4.94 out of 5 average rating, 154 reviews

17th Century Peak District Cottage

Mount Pleasant Cottage was built in the 1600s and is the oldest residential property in the picturesque village of Monyash. This peaceful Peak District getaway is full of character including original oak beams, a wood-burning stove and stunning views of the surrounding countryside as well as a library of fascinating books from around the world. The cottage is just a few minutes walk from the Bulls Head pub and Old Smithy cafe. The cottage lies at the beginning of the stunning Lathkill Dale walk.

Top guest favorite

The shepherd's hut is presented in a tranquil outdoor setting, featuring a wooden staircase leading to the entrance. Surrounding flower pots and a gravel pathway complement the scenery, while lush green hills and distant village buildings create a serene backdrop.

Shepherd’s hut in England

4.97 out of 5 average rating, 312 reviews

Delightful 1-bed shepherd's hut with log burner

Reconnect with nature at this unforgettable escape in the heart of the Peak District. This brand new well equipped Shepherds hut is nestled just outside the village of Cressbrook and boasts stunning views and sunsets over the Wye Valley. The location offers a perfect base for exploring the Peak District with a wide choice of walks or cycle routes from the door. Access to the Monsal Trail is just a 10 minutes walk away, and the villages of Litton and Tideswell are also easily accessible by foot.

Top guest favorite

A spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.

Cottage in Darnall

5 out of 5 average rating, 228 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

Top guest favorite

The charming stone cottage features a warm facade with a mix of natural stone and timber elements. A patio area is visible at the front, bordered by the greenery of the surrounding village. The slate roof and simple window designs enhance the traditional character of the building.

Home in Taddington

4.97 out of 5 average rating, 125 reviews

Romantic Cottage in the Peaks

Romantic characterful stone cottage in lovely Peak District village. Two bedrooms, sleeps four in luxury. Ideal for one or two couples, families with children, and dogs. Perfect for walkers, cyclists and anyone who wants to visit the Derbyshire Dales Family shower room, romantic bath in main bedroom and en-suite shower room in twin bedroom. Centrally heated, large wood burner, beautifully refurbished with quirky interior design. Well equipped kitchen and utility. Outside terrace sitting area.

Top guest favorite

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 in Monyash

4.97 out of 5 average rating, 105 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 favorite

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 in Taddington

4.97 out of 5 average rating, 258 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.

Top guest favorite

The exterior of Leaping Hare Barn is depicted, showcasing rustic stone walls and a staircase leading to the entrance. Potted plants and greenery adorn the patio area, enhancing the natural setting. A gravel pathway leads to the barn, framed by additional landscaping elements.

Barn in Flag

4.98 out of 5 average rating, 507 reviews

Leaping Hare Barn - Rural Barn escape

Leaping Hare Barn is a peaceful, 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 Peace and tranquility Animal 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

Top guest favorite

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 in Bakewell

5 out of 5 average rating, 126 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; with no exaggeration, you really 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, and close to all the main Peak District attractions. Ideal retreat for honeymoon, romantic break or special occasion.

Top guest favorite

The exterior of the cottage features natural stone walls and a pitched roof under a clear blue sky. Two large roof windows provide natural light to the upper floor. A well-maintained lawn is bordered by a quaint stone wall, with a wooden gate allowing entry.

Cottage in Derbyshire

4.98 out of 5 average rating, 277 reviews

Idyllic, The Coach House, Ashford-in-the-Water

A beautiful, recently converted, barn which was originally a Coach House. Totally newly renovated in 2018 this two bed, two bath cottage is set in an idyllic rural location with breath-taking views and direct access across the owners' field to a footpath which leads either down to the famously picturesque village of Ashford-in-the-Water or uphill to the drama of Monsal Head. Separately available is Groom's Cottage, next door, also brand new and sleeping 2 people in equal style.

Top guest favorite

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 in Cressbrook

5 out of 5 average rating, 634 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 favorite

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 in Monyash

5 out of 5 average rating, 275 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.

Top guest favorite

A scenic view captures rolling green hills under a colorful sky at sunset. A tranquil river flows through the valley, with a quaint white building nestled among the trees. A signpost directs visitors towards Monsal Dale, indicating nearby walking paths.

Home in Bakewell

4.97 out of 5 average rating, 117 reviews

Monsal View Cottage

A beautiful space with exquisite views set at the iconic viewpoint of Monsal Head. This is the perfect base to really enjoy all that the Peak District has to offer- including the most epic view of all at Monsal Head and the Headstone Viaduct. Located at Hobb’s Cafe so you have a quaint little cafe right next door! Enjoy breathtaking views all to yourself in the mornings and evenings. Please check out Hobb’s Cafe online to fully see the location of this cottage.