Holiday houses in Winster

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Top-rated holiday rentals in Winster

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

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Top Guest favourite

Cottage in Winster

4.95 out of 5 average rating, 464 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

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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

4.98 out of 5 average rating, 145 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.

ValueLocationOutdoor spaces

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, 282 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

LocationFamilyTV

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, 119 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.

LocationFamilyTV

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, 245 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.

LocationFamilyIndoor spaces

Top Guest favourite

An expansive stone patio is set with a large wooden dining table surrounded by matching chairs. The area is bordered by greenery, with small ducklings walking across the stone surface. A rustic building is visible in the background under a partly cloudy sky.

Cottage in Derbyshire

4.97 out of 5 average rating, 391 reviews

The Barn @ Dale End House, Gratton nr Bakewell

One of just six farmhouses in the rural parish of Gratton, Dale End House is found on a quiet lane in the heart of the Peak District National Park. It enjoys unspoilt countryside, popular with walkers and mountain bikers alike yet is only six miles from Bakewell and Matlock. We discovered Dale End House whilst mountain biking through Gratton Dale and instantly fell in love with it. Surrounded by breath-taking views, and abundant wildlife - Gratton is one of Derbyshire’s best-kept secrets.

LocationFamilyCleanliness

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, 247 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.

FamilyLocationHiking

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, 196 reviews

Boulder Field Cabin and Hot Tub

In the Peak District National Park, nestled amongst the boulders in 5 acres of your own private woodland 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 looking out across the valley, followed by an outdoor shower with stunning views. In the cabin soak up the gorgeous 180 degree views from your cosy bed by the fire, not to mention the glass roof for star gazing!

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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, 304 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

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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, 489 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.

LocationFamilyBiking

Guest favourite

A wooden hot tub is positioned outdoors, surrounded by tranquil countryside. Rolling hills form a scenic backdrop, and a wooden ladder leads to the tub. A peaceful atmosphere is enhanced by the natural setting and distant trees.

Tent in Edale

4.86 out of 5 average rating, 597 reviews

Cozy Couples Glamping - Private Hot Tub

**Updated for 2026** Escapism at its finest. Find yourself rested and renewed at our idyllic glamping site nestled amongst the rolling hills of the Peak District. Updated and improved for Spring - Summer 2026! - We specialise in couples experiences; Birthdays, Anniversaries, Engagements, reach out to us to discuss how we can help make your occasion special. We guarantee that here, you can truly experience the meaning of a retreat.

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Superhost

The living area features a red upholstered chair beside a stone fireplace, which houses a wood stove. A small wooden table stands next to the chair, and a shelf lined with books adds to the cozy atmosphere. Natural light filters through a window dressed in orange curtains.

Cottage in Winster

4.83 out of 5 average rating, 169 reviews

Clover Cottage, Winster, Derbyshire, Peak District

Clover Cottage is a cosy holiday cottage located in the beautiful Derbyshire village of Winster. Full amenities are provided including kitchen, washing machine, towels, linen, fire place, central heating, fast wifi, large TV, DVD, and more. Whether you're exploring the Peak District, visiting friends or attending a wedding at some of the wonderful local venues we're sure you'll have a great stay.

LocationFamilyBathroom