Holiday houses in Wessington

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Top-rated holiday rentals in Wessington

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Top Guest favourite
The exterior of a beautifully renovated stone cottage is depicted, featuring a hot tub on a wooden deck. Large windows reflect natural light, while a manicured lawn surrounds the cottage, enhancing the inviting ambiance of the tranquil setting.
Cottage in Alton Towers
4.99 out of 5 average rating, 154 reviews

Luxury Cottage Green Cottage, Peak District

Unwind in luxury. This renovated cottage is nestled on the outskirts of the Peak District and is the perfect contemporary getaway for anyone looking for serenity. Enjoy the evenings in the garden with the hot tub, spacious patio, and fire pit at the back garden. The Green Cottage encompasses laid-back luxury to the highest standard and is sure to make your stay one to remember. It's a sanctuary for nature lovers, perfect for families, couples, and friends. Alton Towers is only 15 minutes away.

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 Middleton-by-Youlgrave
5 out of 5 average rating, 236 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, 268 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 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 out of 5 average rating, 215 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.

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, 265 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.

Guest favourite
A spacious lounge area features a modern sectional sofa, complete with decorative pillows. Soft light is provided by a standing lamp, highlighting the room's neutral tones. An archway leads towards a dining space that includes stylish pendant lighting, creating an inviting atmosphere.
Cottage in Derbyshire
4.91 out of 5 average rating, 262 reviews

Lizzy’s Luxury Cottage

Welcome to Lizzy’s Cottage! Nestled in the heart of the Peak District, Lizzy’s Cottage offers a luxurious escape for couples and families. Surrounded by breathtaking countryside, the cottage provides a peaceful retreat, while being just a short drive from popular destinations such as Bakewell, Chatsworth, Matlock, and Matlock Bath. At Knabb Farm, we offer private parking for all guests, and our 7 acres of private land provide plenty of space to explore and enjoy the stunning surroundings.

Top Guest favourite
The exterior of a rustic stone barn is shown, featuring a sloped roof and four skylight windows. A side door leads to the interior, while a gravel driveway extends toward the entrance. Surrounding greenery hints at the rural setting and privacy.
Barn in Stretton
5 out of 5 average rating, 145 reviews

Barn conversion in Derbyshire

300 year old barn converted into a two-bedroomed property set on the owner's 5-acre small holding with goats and chickens. Wake up in the morning with a curious goat overlooking the courtyard waiting for a cracker or two. Set next door to the owner's farmhouse but with complete privacy. Located 8 miles out of Matlock on the edge of the Peak District. Pub within walking distance. The nearest town is Clay Cross. The maximum capacity is 4 including children/infants. All fees are included.

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
4.89 out of 5 average rating, 139 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

Top Guest favourite
A modern hut is set on a gravel patio, surrounded by manicured grass. Large glass doors provide views of the interior, complemented by wooden paneling on the exterior. Potted flowers are placed at the entrance, and a seating area is visible in the outdoor space.
Cabin in Derbyshire
4.99 out of 5 average rating, 152 reviews

The Willows Hut - with hot tub - Hillside Huts

The Willows - Hillside Huts - *brand-new August 2025* Our charming, The Willows Hut, is our latest addition, joining The Oaks Hut on our smallholding in rural Derbyshire. With a shared driveway, its own dedicated parking & private enclosed garden, it is situated in a secluded spot enjoying stunning countryside views. Enjoy the most magnificent sunsets as you kick back and relax in this calm, stylish space. Bring your wellies! There are many countryside walks from the from the doorstep!

Top Guest favourite
A spacious wooden deck is highlighted, featuring a dining table and chairs set for outdoor meals. Lush greenery surrounds the area, with distant hills visible under a cloudy sky. Large glass doors lead into the lodge, allowing natural light to enter.
Cabin in South Wingfield
4.98 out of 5 average rating, 290 reviews

Hazel Lodge luxury log cabin

Hazel Lodge is new to Sam’s Derbyshire cottage. This beautiful lodge is set on a working farm between south wingfield and crich. The lodge has 2 bedrooms 1 double and twin rooms, the bathroom is spacious with a shower over the bath. The open plan living kitchen and dinning area is great for entertaining with a 40” smart tv. The hot tub is very private with looks down the valley great for star gazing! There is a big decking area with table and chairs for long nights sat outside.

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 Derbyshire
4.97 out of 5 average rating, 237 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.

Guest favourite
Condo in South Wingfield
4.91 out of 5 average rating, 132 reviews

The Conkers Country Cottage Self Catering Retreat

The Conkers is in the picturesque Hamlet of Moorwood Moor on of the edge of the Peak District. There are many walks from the door and 150 yards along the lane is The White Hart Inn where you will experience good food or just enjoy a well-deserved glass of wine. The Conkers delightful garden and orchard area provides a lovely spot for a relaxing drink, or perhaps some alfresco dining after a busy day exploring. There is ample off road secure parking behind automated gates.

Popular amenities for Wessington holiday rentals

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