Holiday rentals in Flagg

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Flagg

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
The exterior of The Old Chapel is showcased, with its distinctive stone façade and original Gothic-style windows. Lush purple flowers border the pathway, while iron railings enhance the charming entrance. Sunlight filters softly, highlighting the architectural details and creating a serene ambiance.
Home in Ashford in the Water
4.99 out of 5 average rating, 141 reviews

The Old Chapel Luxury Retreat

Introducing The Old Chapel: Following the success and glowing reviews of the Old Bank Bakewell, we embarked on a quest for another unique stay. Enter The Old Chapel, a labor of love renovation resulting in a charming three-bedroom, all-ensuite stay unlike any other. Perfect for short getaways or week-long stays. Enjoy peaceful nights in king-sized beds fitted with luxurious 500-thread-count sheets. Each en-suite features spacious dual showers, fluffy robes, and slippers for ultimate relaxation.

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 in Middleton-by-Youlgrave
5 out of 5 average rating, 236 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
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 Derbyshire
5 out of 5 average rating, 270 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 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 in Bolsover
5 out of 5 average rating, 216 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
A cabin is perched among large boulders, surrounded by lush greenery and distant rolling hills. The exterior features wooden siding and a sloped roof, complemented by a small deck with chairs. The scene highlights a tranquil, nature-focused setting under a cloudy sky.
Hut in Birchover
4.98 out of 5 average rating, 188 reviews

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.

Top guest favourite
A charming stone exterior of the Coach House is highlighted, featuring a large arched entrance and a row of windows. The surrounding trees and blue sky create a serene environment, while the pathway leading to the entrance is flanked by stone walls and greenery.
Home in Bakewell
5 out of 5 average rating, 151 reviews

The Entire Coach House at Middleton Hall

Relax in this peaceful unique country home, either warm yourself by the wood burner or relax out in the garden, taking in the beautiful surroundings of the private Middleton Hall estate. The Coach House has been refurbished , with designer furniture, wall paper, hand painted murals on the walls, marble shower room, hypnos beds and an American fridge freezer. The attractions are wildlife, walking and cycling. Also visiting stately houses like Chatsworth and Haddon. coach-house-middleton.

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 in Taddington
4.97 out of 5 average rating, 273 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 favourite
A spacious open plan kitchen and dining area features a wooden table with rustic metal legs surrounded by six matching benches. Counters are finished in neutral tones with modern appliances, and natural light fills the room through a window, highlighting the stone floor and exposed ceiling beams.
Cottage in Earl Sterndale
4.99 out of 5 average rating, 169 reviews

Hilldale - Stunning renovated cottage in the Peaks

A chic but traditional 17th century recently renovated, into a spacious three bedroom cottage with an abundance of character and unique touches. Located in the White Peak limestone village of Earl Sterndale with stunning views of the distinctive hills of Chrome, Parkhouse and High Wheeldon and the Derbyshire Dales. Hilldale Cottage is perfect for families, friends and couples alike seeking an escape within the Derbyshire Dales. The cottage has a south facing garden with Summerhouse.

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 in Shebdon
4.82 out of 5 average rating, 228 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 in Cressbrook
5 out of 5 average rating, 681 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
Cottage in Monyash
5 out of 5 average rating, 318 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 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 in Taddington
4.99 out of 5 average rating, 157 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.

Popular amenities for Flagg holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Derbyshire
  5. Flagg