Holiday rentals in Upper Town

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Top-rated holiday rentals in Upper Town

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Top guest favourite
Cottage in Winster
4.95 out of 5 average rating, 432 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

Superhost
Cottage in Bonsall
4.76 out of 5 average rating, 242 reviews

Peak District hideaway with hillisde terraces

Weavers Cottage is in the lovely village of Bonsall on the edge of the Peak District National Park. Numerous walks begin in the village; it's great for cyclists, climbers and canoeists. Two great pubs and a village shop mean you never have to leave. Extensive hillside garden with outdoor seating and lots to explore. Numerous attractions nearby ranging from historic (Chatsworth Hall, Haddon Hall, Bakewell...) to fun and games for kids in Matlock Bath (Gullivers Kingdom, Heights of Abraham)

Guest favourite
A charming limestone holiday home is positioned on a hillside, surrounded by vibrant wildflowers. The property features a private patio that opens up to the countryside. The natural landscape includes lush greenery and a variety of flowering plants, enhancing the outdoor setting.
Cottage in Bonsall
4.89 out of 5 average rating, 347 reviews

Countryside Retreat

Hillside is a recently built limestone self contained holiday let, on the edge of a pretty Derbyshire village. Hillside overlooks the village of Bonsall (near Matlock) offering beautiful views from the windows and private patio of the village and surrounding countryside. Bonsall offers an excellent pub, cafe and village shop. There are numerous walks from the doorstep - the Limestone Way passes through the village. Chatsworth, Bakewell, Dove Dale and the Monsal Trails are all a short drive away.

Top guest favourite
The stone exterior of the barn conversion is highlighted by its natural texture and warm tones. A large window with trim enhances the entrance, while vibrant lavender flowers border the pathway, offering a touch of color against the rustic backdrop.
Barn in Matlock Town
4.94 out of 5 average rating, 143 reviews

A contemporary, romantic hideaway in Derbyshire

Spacious, comfortable stone barn conversion with stunning views, private patio and parking situated close to Matlock. A great place to relax & unwind after exploring the Peak National Park. Watch Buzzards soar and the cows graze while the sun sets from the front terrace or cook up a feast on the BBQ. Explore all that the Peak District has to offer - walking, climbing, cycling, wild swimming & water sports at nearby Carsington. Chatsworth House, Haddon Hall, Bakewell are all a short drive away.

Guest favourite
The renovated stone barn features a tidy exterior with a porch and flower beds filled with colorful plants. A gravel driveway leads to the entrance, and a spacious lawn area is visible. The surrounding hills create a serene countryside backdrop.
Home in Middleton
4.9 out of 5 average rating, 187 reviews

Cheerful 2-bedroom home with free offroad parking

Explore all the peaks has to offer with this beautifully renovated field barn. Free offroad parking, garden area. Two bedrooms, two bathrooms. Open plan downstairs gives a airy homely feel. Within easy access of footpaths and trails close to the famous quarries of derbyshire dollermite and limestone. Secluded location yet within easy reach of Wirksworth the nearest town just 5 minutes away and the beautiful village of carsington just over the hill. 2.3m Wirksworth 5.8m Matlock 1.6m Carsington

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 Bonsall
5 out of 5 average rating, 259 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, 201 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 private patio area features a circular stone table surrounded by four metal chairs with fabric seats. A bottle of champagne and glasses are positioned on the table, while a wooden fence and flowering plants provide a backdrop.
Cottage in Bonsall
4.95 out of 5 average rating, 209 reviews

Study Farm Cottage - Sleeps 2 - Scenic location

The cottage which dates from 1845, is situated in Bonsall village, high above the wooded 'Via Gellia' gorge. Matlock Bath is 2 miles by car or a scenic walk through woodland. Superb walks from the door to the limestone moors above. Within easy driving distance of Chatsworth, Haddon Hall and Arkrights Mills. Crich Tramway Museum and Carsington Water. Bonsall has two pubs and a Tea Room a few minutes walk from the property. Bonsall Carnival week starts on the last Saturday of July every year.

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
5 out of 5 average rating, 483 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.

Top guest favourite
The lofted space features exposed wooden beams and rustic stone walls, creating a sense of historical charm. A potted plant is positioned near a low railing, overlooking the open area below, which includes cozy seating and ample natural light streaming through large windows.
Barn in Bonsall
4.91 out of 5 average rating, 188 reviews

Magical Historic Barn Conversion

This barn is not for everyone; it is no ordinary holiday cottage, but a retreat for the senses. A unique chance to step back in time, a place where time stands still. The antidote to the fast-pace of life, up here you will feel as though you’re in another world. This 17th century barn is a love note to its 1960s conversion, with all its quirky features still intact. There are no screens, the lighting is low and warm, you will not hear a sound apart from the birdsong. For some, it is heaven.

Guest favourite
A private terrace features a small table with two chairs, surrounded by stone walls. The stunning view showcases green hills and a partly cloudy sky. The rustic charm of the cottage's stone rooftop and chimneys adds to the peaceful ambiance.
Home in Bonsall
4.88 out of 5 average rating, 180 reviews

Pigeon Loft Cottage

This unique self contained peaceful cottage is 250 years old and set in the centre of the beautiful village of Bonsall in the Peak District and within easy reach of all amenities. The cottage was once a Pigeon loft and has been transformed and renovated into a simple characterful living space within the conservation area. Views from the cottage and outside private terrace are stunning. There are choices of walks from the door including 2 pubs and cafe within easy walking distance.

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, 209 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.

Popular amenities for Upper Town holiday rentals

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  4. Derbyshire
  5. Upper Town