Holiday rentals in Wessington

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Top-rated holiday rentals in Wessington

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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
5 out of 5 average rating, 261 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
5 out of 5 average rating, 207 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 charming log cabin is seen from a pathway lined with autumn leaves, illuminated by warm string lights. The front door opens to a welcoming entrance, framed by lush greenery and decorative plants, suggesting a cozy and inviting atmosphere.
Tiny home
4.99 out of 5 average rating, 441 reviews

Hot tub, Peak District, Walks, Romantic, Cabin

Trickle Brook Cabin is a unique log cabin, a rustic converted shed, accessed via a bridge over a stream and nestled in a tranquil spot in the picturesque village of Wincle in the beautiful Peak District, tiny cabin with external measurements of 4 metres x 5 metres, cozy and very romantic. An excellent Short break, birthday, anniversary gift or wedding proposal or just a place to chill out and relax. A complimentary bottle of Prosecco awaits your arrival. See other listing for Brookside Cabin

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
4.91 out of 5 average rating, 255 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 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
4.89 out of 5 average rating, 138 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
5 out of 5 average rating, 134 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 charming country farmhouse is positioned among vibrant flowerbeds filled with sunflowers and colorful blooms. The home’s stone exterior is complemented by large windows reflecting the blue sky. Lush greenery frames the entrance, inviting guests to explore the surrounding gardens.
Holiday home
4.96 out of 5 average rating, 148 reviews

Peak District Country Farmhouse

Beautiful country farmhouse situated down a 250m private drive on the outskirts of the village of Tansley. On the hillside below Riber Castle the property is surrounded by horse pastures and farmland. There are stunning views from every window. The house has been completely renovated with the input of an interior architect to an extremely high standard. Many of the original Victorian features have been retained and stylishly combined with a super modern kitchen and bathrooms.

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
4.98 out of 5 average rating, 283 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
4.97 out of 5 average rating, 231 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
A comfortable living area features exposed wooden beams and a cozy sofa. A wooden coffee table sits in front, with a television mounted nearby. Natural light enters through a window adorned with soft blinds, creating an inviting space for relaxation.
Apartment
4.91 out of 5 average rating, 130 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.

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
4.85 out of 5 average rating, 538 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.

Top guest favourite
A spacious interior features a warm wood-burning stove adjacent to a comfortable sleeping area. Two inviting armchairs are placed upon a soft area rug. Natural light streams in through the skylight and window, illuminating the simple, yet elegant decor.
Barn
5 out of 5 average rating, 128 reviews

Beautiful barn conversion.

Reconnect with nature at this unforgettable escape on the edge of the Peak District. Beautifully finished barn conversion. King sized bed, tv with full Sky package. Log burner. Bathroom with freestanding bath and separate shower. Fully equipped kitchen. Outside seating/bbq area. Village and pubs within walking distance. Fantastic walking area. Stunning views. Plenty of parking.

Popular amenities for Wessington holiday rentals

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