Vacation rentals in Flagg

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.

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

This two bed cottage is in an idyllic rural location with breath-taking views. Walk through fields onto a footpath down to the picturesque village of Ashford-in-the-Water or uphill to the drama of Monsal Head. *Please note - bathroom refurbishment (completed 1st March 2026) The Coach House will still offer one full family bathroom for guests to share (with sink, loo, shower-over-bath). The new en-suite ‘dressing room’ will contain a sink, toilet and vanity area but no longer a separate shower.

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.

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.

Boulder Field Cabin and Hot Tub

Nestled amongst the boulders in 5 acres at the top of Eagle Tor this beautifully hand crafted cabin is the ultimate romantic getaway. Relax and get back to nature in the gorgeous wood fired hot tub set on a boulder looking out across the valley, followed by an outdoor shower nestled amongst the rocks. In the cabin soak up the gorgeous 180 degree views from your cosy bed, not to mention the glass roof for star gazing! A covered outdoor kitchen/eating area and a firepit to toast marshmallows.

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.

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

Litton Mill Retreat, Luxury Converted Mill

Nestled in the heart of the Peak District National Park, Litton Mill is a beautifully converted former watermill just minutes from the Monsal Trail. Recently renovated, the large apartment is 1,400 sqft & features a stunning open plan living, dining and kitchen space filled with natural light. Two spacious en suite bedrooms offer super king beds (or twins), each with an additional pull-out single bed, making it ideal for couples, families or groups.

“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.

Hawthorn Cottage - Romantic Getaway with Hot Tub

Step back in time to 1672 with a romantic stay at Hawthorn Cottage, a charming thatched retreat full of character. Original low beams, an inglenook fireplace, and a cranked staircase blend with modern comforts including underfloor heating, a fully equipped kitchen, and a bathroom with bathtub. Outside, enjoy countryside views, an enclosed garden, and your own private hot tub.