Holiday houses in Woolley Moor

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Top-rated holiday rentals in Woolley Moor

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

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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

5.0 out of 5 average rating, 247 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.

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Guest favourite

A modern kitchen diner features wooden cabinetry and a spacious table with room for six. A bouquet of flowers sits at the center of the table. Appliances include a refrigerator, microwave, and dishwasher, while tiled walls display a mix of earthy colors.

Cottage in Clay Cross

4.91 out of 5 average rating, 292 reviews

Holly Cottage a great place for a country break

Holly Cottage is a stylish contemporary barn conversion combining cottage charm with spacious accommodation and excellent modern facilities in a lovely rural setting. Set in the grounds of a small farm and private stables with lovely views of the of the surrounding countryside. Ideally situated for exploring the Peak District and local area. Holly Cottage offers a spacious modern Kitchen diner, a cosy sitting room with TV also two good size double bedrooms, modern bathroom and outside space.

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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

5.0 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

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Top Guest favourite

An inviting outdoor terrace features a wooden hot tub adjacent to a well-placed seating area, which includes a coffee table and decorative plants. Lush greenery is visible in the background, while sunlight brightens the space, creating a serene atmosphere.

Cabin in Anslow

4.99 out of 5 average rating, 542 reviews

Tilly Lodge

Unwind in luxury in this brand-new converted lodge. With a hot tub and seating area overlooking some fantastic views alongside a gorgeous modern interior. This getaway is perfect for couples, families and friends. Built by my wonderful talented husband Tilly Lodge is a self contained luxury getaway surrounded by so many local attractions some being just a stones throw away. Tilly Lodge is set in a beautiful village with a lovely pub, fabulous garden and great food just a 4 minute walk away.

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Top Guest favourite

The exterior of the detached garage features a two-story design with a red tiled roof and large garage doors. A gravel driveway leads to the entrance, while an outdoor staircase provides access to the apartment above. Lush greenery surrounds the property, enhancing the rural setting.

Guest suite in Derbyshire

4.9 out of 5 average rating, 155 reviews

Ford Farm Annex, Ogston, Higham, Derbyshire

The private apartment is situated above our 3 bay detached garage, within the grounds of our home. We live down a quiet country lane giving the feeling of a rural location, but within a few miles of Matlock. It offers the freedom of modest self-catering accommodation, ideal for short breaks, the minimum stay is 2 nights. Ford Farm is good for couples and solo or business travellers, but limited to two peopIe. It is an ideal base for walking, cycling and exploring the Peak National Park

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Top Guest favourite

A serene sleeping area features a wooden bed dressed with a yellow patterned throw, complemented by fluffy towels. A cozy armchair provides additional seating. Large windows frame the view, allowing natural light to illuminate the space, while warm tones create a peaceful ambiance.

Guest suite in Ashover

4.98 out of 5 average rating, 254 reviews

Self-contained studio in amazing rural location

This comfortable studio with amazing views, lots of outdoor space, walks from the doorstep and pubs with good food nearby is perfect for couples looking to re-charge their batteries in a rural location. It has a well-equipped kitchen, including dishwasher, White Company linen, underfloor heating with independent controls, it's own combi-bolier for hot water, tv and wi-fi. It is on the edge of the Peak District with many local attractions, such as Chatsworth and Hardwick Hall.

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Top Guest favourite

A modern open-plan living area features a well-equipped kitchen with a marble countertop and dark cabinetry. A vase with fresh roses sits on the counter. A comfortable sofa is observed in the background, alongside a decorative wall with framed artwork and a television.

Loft in Ashover

4.98 out of 5 average rating, 238 reviews

Fairfield Loft, Ashover - Village hideaway for two

Fairfield Loft is in the heart of the lovely village of Ashover with the beautiful Derbyshire Dales and Peak District National Park right on the doorstep. Tucked away behind Stamp, our coffee shop and village post office, the space was renovated in 2021 with comfort and quality in mind. There's lots to see and do in the area but if you simply want to relax then spend the days exploring the many beautiful local walks and maybe wind down in one of the friendly local pubs.

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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 charming stone cottage is visible, framed by lush greenery and flowering plants. The two-story structure features a sloped roof and a chimney, with a pathway leading to the entrance. Rolling hills are seen in the background, under a partly cloudy sky.

Home in Ashover

4.98 out of 5 average rating, 133 reviews

Country Cottage with great outside space & views

Relax in our stunning two-bedroom slice of Derbyshire heaven! Amazing walks and local pubs >1 mile away. Large terrace with fabulous views over the valley & a range of seating. 2 double bedrooms, 1 then & large family bathroom. Significant renovations recently & has a highly specified kitchen inc. range. Log burner in living room & Smart TVs in Kitchen, Living room & main bedroom. WIFI & office to keep in touch with work whilst relaxing in comfort & style.

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Guest favourite

A charming stone cottage with a slate roof is set among gravel landscaping. A vibrant green door, adorned with diamond-shaped glass, is framed by neatly trimmed boxwood hedges. A small potted tree adds a touch of greenery to the inviting entrance.

Barn in Clay Cross

4.85 out of 5 average rating, 577 reviews

Stretton Hall Farm - The Annex

Our holiday cottages & glamping pods are located on our 100 acre farm on the edge of the Peak District. The Annex is a modern barn conversion with a luxurious interior, designed to make it feel like a home away from home. Secluded down a 1/4 mile private driveway in a courtyard with the other cottages, the Annex has a quiet feel to it where you can truly relax. We are contractor friendly, please message us for work stays that are Monday to Friday.

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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.

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Superhost

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, 598 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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