Family-friendly vacation rentals in Bakewell

Stylish cottage inc breakfast, 4 adults 2 children

• FREE breakfast every day at The Old Original Bakewell Pudding Shop • Welcome basket on arrival: loaf of Bakewell Bakery bread, pint of milk, bottle of wine, bottle of Bakewell Best Bitter and an award-winning Original Bakewell Pudding • Within a minute’s walk of shops, pubs, cafes, the River Wye and a large park • Walking, climbing and cycling on the doorstep • Outdoor area for al fresco dining • Cosy log burner in the living area • One parking space included • Free WiFi • Dogs allowed

The Pudding Stop - Bakewell - Free Parking

Our beautiful and newly refurbished (2023) cottage is right in the heart of Bakewell, Derbyshire. The location could not be more convenient - it's a minute walk into the centre where you will find excellent pubs, restaurants, cafes and independent shops. We now also include free on-street parking. The Pudding Stop sleeps 2 guests (babies and dogs welcome too!) and is available for short breaks and week stays. This little hideaway is set within the garden of our 1830’s Grade II listed property.

Milford Cottage in Bakewell with parking

A beautiful one bedroom Grade II Listed cottage in a courtyard centrally-located in Bakewell with a parking space for a small to medium sized car directly in front of the cottage. Milford Cottage has been lovingly renovated to a high standard, a homely and comfortable retreat, ideal for couples. Perfectly located just a short stroll alongside Milford Stream into the beautiful town of Bakewell offering a great selection of shops, cafes, pubs & restaurants. Stunning walks from the doorstep.

Millstream Cottage

A Charming Grade 2 listed stone built terraced cottage with an allocated parking space outside the property, conveniently located in the picturesque market town of Bakewell. Very quiet but ideally positioned to explore the beautiful Peak District. There is a bus stop nearby where you can access transport to Manchester and Sheffield. Ideal for families or couples. Highchair and travel cot available on request. A welcome pack will be provided on your arrival to get your stay of to a great start.

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

The Kennels

Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

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. ** Pets allowed on request ** 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.

Luxury & Location! Bakewell Georgian Townhouse

LAST MINUTE AVAILABILITY NOVEMBER ‘25!! Enjoy the best of the best at this 70sqm luxury Georgian Heritage Listed Townhouse, The Haywood with free parking directly behind the property. Perfect location right in the heart of Bakewell with the River Wye, cafes, boutiques & pubs all within a few minutes walk, the property has just been entirely renovated by a team of local craftsmen & interior designers and is intended to provide a luxe, spacious & relaxing oasis for a short or longer break.

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

Jack's Cottage, Curbar

Sleeping on a cloud under Curbar Edge. Take it easy at Jack's Cottage, a boutique 17th century stone built luxurious cottage in the heart of the Peak District. Enjoy a soak in the hydrotherapy hot tub or cosy up in front of the log burner. Located next to the historic well in the centre of the village with a fully fenced private garden, bring your dog along to explore amazing walking and cycling from the doorstep. Secure alarmed bike store with wall anchor & charge for ebikes.

A beautiful barn in the heart of the Peak District

Bottom Cottage is nestled in the heart of the Peak District National Park. This cosy barn has been recently and sympathetically converted to a one bedroom, one bathroom detached annex, perfect for a weekend getaway. Situated in a delightful, quiet hillside village, the cottage is within walking distance to pubs, shops and beautiful hiking and cycling routes. Chatsworth House, Bakewell, Haddon Hall and the Monsal Trail are just some of the attractions in the area. Sleeps 2+2.

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.