Holiday houses in Winster

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Top-rated holiday rentals in Winster

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Top Guest favourite
Cottage in Winster
4.95 out of 5 average rating, 449 reviews

Gorgeous romantic cosy cottage retreat with views

Welcome to Lancaster Cottage, Winster - the perfect luxury escape for couples in the Peak District. ~ Ideal cosy hideaway for a romantic escape for 2 ~ Secluded, off-road & immersed in nature with secret garden & log cabin ~Fabulous walks from the doorstep ~Lovely pubs within a few minutes walk ~Oozes character - built in 1701 & Grade II Listed ~ Cosy woodburner fireplace & beams ~Huge sink-in settee & a dreamy, romantic bedroom with king-sized comfy bed with stunning views ~Dog-friendly

Top Guest favourite
Cottage in Bakewell
4.99 out of 5 average rating, 239 reviews

Rocking Stone Cottage - Idyllic Rural Retreat

Perfect for two couples or a family an immaculate contemporary cottage in the Peak National Park, a stones throw from Chatsworth. A perfect spot to get away, relax and explore the stunning countryside right from the door. The cottage features beautiful outdoor spaces, a large stone fireplace with woodburning stove, wooden shutters, exposed beams, a fully fitted hand made kitchen, walk in rain showers and romantic roll top bath. BBQ on one of the two terraces or just relax and take in the view.

Top Guest favourite
The charming exterior of the cottage is adorned with a flowering wisteria, adding a touch of natural beauty. The stone facade features large windows and French doors that open into the courtyard, complemented by a small seating area with two chairs.
Cottage in Winster
4.99 out of 5 average rating, 134 reviews

Anvil Cottage, lovely cottage in the Peak District

Anvil Cottage sits within its own private courtyard and is a light and airy detached barn conversion, full of charm and character. Over 200 years old, the cottage has been refurbished in 2022. Sleeps 3 in 2 bedrooms, pet free, and ideally situated in the heart of the historic village of Winster for walking and touring the beautiful countryside of the Peak District National Park. A short stroll to the friendly local community shop and pubs. Within easy reach of Matlock, Bakewell and Chatsworth.

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 Youlgreave
5 out of 5 average rating, 240 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, 274 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 modern detached bungalow showcases a stone exterior, complemented by well-maintained gardens. The expansive driveway accommodates multiple vehicles, while lush greenery in the background enhances the tranquil setting. Large windows invite natural light into the living space.
Bungalow in Bakewell
4.99 out of 5 average rating, 149 reviews

Modern bungalow with two bedrooms: king and double

Modern detached bungalow with king and double bedrooms, set in a quiet street just a 10-minute flat walk to the heart of Bakewell. The property offers a spacious lounge and conservatory looking out onto a mature garden, a well-equipped kitchen and ample driveway parking. An ideal base for exploring the Peak District, with Chatsworth House, Haddon Hall, and scenic country walks. Bakewell offers a range of restaurants, cafés, traditional pubs, independent shops, supermarkets and weekly market.

Top Guest favourite
The entrance to the stone cottage is framed by weathered stonework, featuring a light-colored door with three clear panes at the top. Potted flowers in vibrant colors sit on either side, adding a welcoming touch to the doorway.
Cottage in Winster
4.98 out of 5 average rating, 110 reviews

Picturesque Rose Cottage in Winster

Relax in this pretty stone cottage. The cottage is perfect for a romantic break or a base for exploring the local countryside. Ideally located in the pretty village of Winster, in the Derbyshire Peak District, between Matlock and Bakewell. Winster is surrounded by beautiful rolling hills, characterised by the limestone cliffs and drystone walls typical of the White Peak. There are very many walks and cycle routes starting and ending in the village, and the whole area is well worth exploring.

Top Guest favourite
A stone exterior of the building is highlighted, featuring a prominent navy-blue door framed by two windows. Soft lighting enhances the entrance, surrounded by a neatly landscaped area with low shrubs and pavers leading to the door.
Cottage in Matlock
4.99 out of 5 average rating, 271 reviews

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.

Top Guest favourite
A rustic Japanese whirlpool bath made from cedar wood is displayed in the private garden. Water cascades from two ornate taps into the inviting bath, surrounded by natural greenery and wooden slats for added privacy.
Farm stay in Winster
5 out of 5 average rating, 231 reviews

Courtyard Cottage -With Japanese Whirlpool Bath

Welcome to the charming Courtyard Cottage, a luxurious escape on a small working farm in the rolling hills of the Peak District National Park. Surrounded by breathtaking views in every direction, this beautiful holiday cottage is the perfect base to explore one of England’s most picturesque regions. Whether you're seeking a romantic weekend away or a quiet rural break, Courtyard Cottage offers an outdoor Japanese whirlpool bath, panoramic views, and cosy interiors for an unforgettable stay.

Top Guest favourite
The Dutch Barn is viewed from the lawned area, showcasing its modern design with large glass panels. A flight of stairs leads to the entrance, while surrounding trees and a manicured grassy area enhance the serene setting.
Barn in Wensley
4.96 out of 5 average rating, 224 reviews

Converted Dutch Barn, Wensley

Situated in the quiet village of Wensley is The Dutch Barn which probably boasts the best views across the dale towards Riber Castle in the Peak District National Park, walks from the doorstep too. It is a spacious but cosy, bright, open plan building which sleeps 2 and has a modern bathroom. It is situated near Matlock and just 7 miles from the lovely town of Bakewell and the famous Chatsworth house. It offers a tranquil stay with secure off road parking and garage facilities too.

Top Guest favourite
A spacious outdoor seating area is highlighted by a large umbrella providing shade over a table with four chairs. The surrounding garden features a variety of colorful plants and flowers in pots, enhancing the natural setting. The stone barn wall is visible in the background.
Cottage in Winster
4.99 out of 5 average rating, 299 reviews

3 bed, 2 bath with off road parking for 2 cars

The Old Barn offers a character barn in a village location, off road parking for 2 cars, short stroll to local shop and pubs - all modern fittings including SkyTV, DVD, and wifi, 3 bedrooms (2 on ground floor, 1 on first floor) 2 bathrooms (1 on ground floor, one on first floor). Excellent and extensive walking from doorstep, outbuilding available for bike storage. All lovingly cleaned and maintained by owner Sharon. Newly refurbished for 2022

Top Guest favourite
An outdoor seating area features comfortable lounge chairs on a grassy patio, with a wooden deck extending towards a Japanese whirlpool bath. Large glass doors provide access to the interior, framed by wooden beams under a clear blue sky.
Cabin in Bakewell
4.92 out of 5 average rating, 478 reviews

Air conditioned Woodcutters ~ Romantic Retreat

✨ Romantic Air-Conditioned Cabin with Whirlpool Bath & Couples Spa 💖 Escape to Woodcutters Cabin — a luxury hideaway for two in the heart of the Peak District. Enjoy your private Japanese whirlpool bath with mood lighting, a plush super-king bed, and a secret shower-room door. Treat yourselves to candle-lit couples massages in our tranquil treatment room. A peaceful, baby, child-free, pet-free retreat made for romance and total relaxation.

Popular amenities for Winster holiday rentals

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