Holiday rentals in Osmaston

4.95 out of 5 average rating, 347 reviews

Cottage in Fenny Bentley

Luxury Peak District Home - 2 miles from Ashbourne

Curl up on the massive leather sofa in front of the log burning stove or chill by the outdoor heated pool (June, July, Aug only). Relax in rural peace or explore local Georgian gem Ashbourne, just 2 miles away. Walk directly to Tissington, Dovedale and The Stepping Stones and beyond from your back door. Chatsworth House is only 30 mins away. Antiques, books, games, dvd's, pure cotton linen. 5 acre garden with Wendy House and croquet. Award-winning Callow Hall is just 5 mins away. Fibre Optic

4.99 out of 5 average rating, 157 reviews

Barn in Derbyshire

The Stables- Stunning contemporary barn conversion

Stunning contemporary retreat for two in a converted stable building. Enjoying a fantastic location, nestled at the bottom of Thorpe Cloud in the Peak District. From the door step you will discover a wealth of country walks and cycle trails for all abilities to enjoy in the magnificent surroundings of the Peak District. An area of outstanding natural beauty, close to Ashbourne, within easy reach of Bakewell, Buxton, and for a fun filled day out, Alton Towers. Excellent Pub 5 mins walk away!

4.92 out of 5 average rating, 170 reviews

Home in Shirley

The Long Shed Livery & AirB&B

Based in the Gateway to the magnificent Peak District we are offering our freshly renovated lodge style annex guest house. Only 5 Min drive from the beautiful market town of Ashbourne we have everything here from relaxation and peaceful breaks to white knuckle Theme parks like Alton Towers or maybe for those ramblers out there we have the best of the best within a 20 minutes drive, or peaceful woodlands and rolling hills at the end of our private driveway. Our local pub (The Saracens) is a MUST

5 out of 5 average rating, 218 reviews

Cottage in Darnall

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

5 out of 5 average rating, 221 reviews

Atlow Mill - award winning 5 bed accommodation

** Winners of Self-Catering Accommodation of the Year 2025! ** On the edge of the Peak District, in it's own private valley, Atlow Mill is a 17th century water mill, full of character. Sympathetically renovated throughout, The Mill offers 5 bedrooms, 3 bathrooms, a log burner, large kitchen, and a private garden with hot tub, gas BBQ and wood fired pizza oven. It is surrounded by rolling hills, a pretty brook and secluded woodland, and The Red Lion pub is just half an hour's walk away.

5 out of 5 average rating, 110 reviews

Barn in Bradbourne

The Old Cattle Barn, Peak District - Valley View

A beautifully renovated stone barn, set in the grounds of a Grade 2* listed farm dating back to 1640. Meticulously transformed from the original cattle stalls into a modern, perfectly rustic two-bed, two-bath cottage in 2023, it retains the history and character of the original building. From this idyllic rural location on the Peak District National Park boundary, there are breathtaking valley views across Bradbourne Brook, and yet the barn is only a 10-minute drive into Ashbourne.

4.94 out of 5 average rating, 221 reviews

Cottage in Mayfield

Cheerful period cottage overlooking the River Dove

A cosy and happy place, restored from a farmers terrace cottage situated on the Staffordshire Derbyshire border looking over the River Dove. Ideally located in the historic village of Mayfield close to the market town of Ashbourne, gateway to Dovedale and the Peak District. Convenient off road parking and a great location from which to walk, cycle and explore beautiful middle England. With Carsington Water and Alton Towers near by and convenient pubs, restaurants and coffee bars.

4.87 out of 5 average rating, 321 reviews

Country Cottage Close to Alton Towers. Ashbourne

Strawberry Cottage is located in the parish of Clifton on the outskirts of the Peak District National Park and set amidst stunning scenery only a short distance from the lovely market town of Ashbourne with its interesting streets and cobbled alleys. Excellent location for those loving the outdoors guests will find an abundance of activities. This wonderful property has comfy beds, cosy living area with log burner and smart TV with full access to Netflix and wifi connection.

4.99 out of 5 average rating, 269 reviews

Beautiful barn near Dovedale.

Welcome to Rickyard Barn! This barn is located perfectly to explore the stunning Peak District and surrounding areas. Under 1 mile away from the Dovedale Stepping Stones, 1.5 miles away from the beautiful Tissington estate, 500 yards from the Tissington trail bridleway, footpath and cycleway, Under 4 miles to the market town of Ashbourne and just 25 mins away from Alton Towers resort. Private Parking &Outdoor space, Excellent Pub 100 yards away! Thankyou

4.99 out of 5 average rating, 489 reviews

Cottage in Clifton

Cottage near to Alton Towers and the Peak District

Welcome to Flower Gardens! This idyllic little chocolate box cottage lies in the beautiful, peaceful village of Clifton, a mere 15 - 20 minute drive from Alton Towers and a leisurely 15 minute walk to the beautiful market town of Ashbourne, gateway to the Peak Dristrict. Nestling on a quiet road, surrounded by doorstep walks and overlooking the church, this little home from home offers everything you could desire for your well deserved break.

4.96 out of 5 average rating, 205 reviews

The Hayloft - in the Peak District near Ashbourne.

The Hayloft is a spacious studio apartment surrounded by beautiful Derbyshire scenery in the tranquil village of Bradley near Ashbourne. There could hardly be a more peaceful setting, surrounded by fields and with Mill Dam Lake on the opposite side of the road. The surrounding area is ideal for walking, cycling and outdoor pursuits with the Tissington Trail, Dove Dale & major attractions like Chatsworth House & Alton Towers within easy reach.

4.96 out of 5 average rating, 180 reviews

Flat in Bournville

Station Street Town Apartment

A delightful spacious one bedroom self-catering apartment on the ground floor. This apartment is perfect for those wanting to experience a relaxing break or an adventure packed one. This modern apartment is in the town centre which makes it a perfect place to stay for those who want to explore the bustling market town of Ashbourne. There's locked outdoor shed for bicycles.

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Other great holiday rentals in Osmaston

5 out of 5 average rating, 53 reviews

Apartment in Derbyshire

Grade 2 listed Coach House Apartment Sleeps 4

CarolineRating, 5 stars6 days ago

We had a fantastic stay, loved every minute. Geraldine is a lovely host - she and her family were friendly and welcoming - we were very well looked after during our stay. The house is in a gorgeous location - the village is beautiful and peaceful but is still in easy reach of nearby towns and local amenities if needed. We had some lovely walks during our week - the countryside is stunning. A fabulous property - full of character and has the most lovely feel to it. The furnishings are of a high quality and the house is very well equipped - we were so comfortable and we had everything we needed for our stay. We will absolutely definitely be back - very soon we hope!

Guest house in Derbyshire

4.99 out of 5 average rating, 282 reviews

The cabin @ white cottage

AbhishekRating, 5 stars5 days ago

This place was magical. Had amazing view from the garden, private space like we wanted, cosy stay. Hannah was quick & responsive, prepared the hot tub and organised everything for us. Worth every penny. Highly recommend.

Guest house in Bournville

4.99 out of 5 average rating, 117 reviews

The Stables, Ashbourne

KatRating, 5 stars2 weeks ago

Thank you, Barbara, for a wonderful weekend away! 🐶 The Stables is simply stunning, with a generous living space, beautifully finished with plenty of lovely personal touches - some bakewell tarts awaited on arrival, alongside some butter and milk in the fridge and bread on the side. Barbara was a wonderfully friendly and attentive host, who gave me a tour of the space when I arrived and showed me how to use everything. My dog, Charlie, and I felt right at home in this cosy space, with beautiful views right on the doorstep. There is so much to explore nearby and The Stables was a wonderful 'basecamp' to return to after a long walk, to relax and unwind. We'll definitely be back!

4.86 out of 5 average rating, 215 reviews

Cottage in Staffordshire

Dove Cottage, only 3 miles from Alton Towers

ThrenoRating, 5 stars2 weeks ago

I had a wonderful stay here—it truly felt like a home away from home. The atmosphere is warm and welcoming. The place is neat, clean, and well-maintained. The host is extremely friendly and supportive, making the stay even more comfortable. Highly recommended for anyone looking for a cozy and pleasant place to stay.

4.94 out of 5 average rating, 32 reviews

Home in Bournville

Homelea 2 Bed Bungalow Ashbourne

StevenRating, 5 stars1 month ago

Had a lovely few days in Ashbourne. Bungalow lovely with a large sitting room/dining room with open plan kitchen. Large back garden that we were able to enjoy having had beautiful weather. 15 min walk into town down hill - but meant 15 min walk uphill - we caught a bus once. 😀

4.88 out of 5 average rating, 492 reviews

Cottage in Wirksworth

Quaint 2 bed cottage, ideally located for walking

MathewRating, 5 stars2 weeks ago

The Old Chapel is a perfect escape from the busy pace of life. It’s cozy, full of character, and surrounded by beautiful, peaceful gardens that make you feel right at home. We planned to explore the Peak District but ended up spending two relaxing days just enjoying the cottage and its surroundings. Host Sarah’s artistic touch is evident in every corner. Well-equipped and welcoming—highly recommended for couples and families.

5 out of 5 average rating, 331 reviews

Cabin in Anslow

Tilly Lodge

MichaelRating, 5 stars2 days ago

My wife and I stayed at Tilly lodge for our 'mini-moon'. What can I say, the lodge was incredible. Everything about our stay was of the highest quality. You can tell home much thought and consideration to guests is given by Sam. Lots of little touches to make our stay unique and memorable. We opted to include a luxury package which made our stay even more special. On arrival we had lovely decorations as well as prosecco and a freshly baked cake waiting for us. The hot tub was so relaxing and the beautiful countryside was so peaceful. We would highly recommend Tilly Lodge and look forward to returning!