Vacation rentals in Grassmoor

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Top-rated vacation rentals in Grassmoor

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Guest favorite

Guest suite in New Tupton

4.85 out of 5 average rating, 255 reviews

Studio Annexe on the Edge of the Peak District

A bright and airy ground floor annexe, used solely for guests. With its own entrance, a comfortable double bed, fully equipped kitchen and outdoor patio area, you are guaranteed a relaxing and private stay. Nestled away in the village of Tupton on the edge of the Peak District, we hope that you can find a place to relax, eat and explore. If you're with us for work, moving house or to see family, then we have everything you need from pots and pans to a washing machine as well as a space to park.

Oct 9 – 16

R1,374 ZAR per night

Guest favorite

Cottage in Chesterfield

4.92 out of 5 average rating, 223 reviews

Chatsworth Cottage

Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

Aug 9 – 16

R2,756 ZAR per night

Guest favorite

Condo in Holymoorside

4.98 out of 5 average rating, 101 reviews

Dog Friendly, Cosy, Peaceful, Walks, Peak District

The Spinney is our super dog-friendly ground floor self-catering accommodation! We've designed it so that you & your dog have a great holiday! Part of a traditional stone barn conversion located in the Peak District & Derbyshire Dales, the Spinney offers space as well as the comfort of modern living. With cosy underfloor heating throughout, and everything you need for you and your furry friend, we are sure you will have a great time here! Peaceful setting, close to popular visitor attractions!

Apr 11 – 18

R2,036 ZAR per night

Guest favorite

Home in Wingerworth

4.9 out of 5 average rating, 199 reviews

Oakdale - Our Quest retreat

Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

Sep 12 – 19

R1,806 ZAR per night

Guest favorite

Guest suite in Ashover

4.97 out of 5 average rating, 276 reviews

Hunger Hill Farm Studio - Derbyshire Dales

Set in the glorious Peak District in a rural location is our lovely self contained studio. Glorious views over rolling countryside and very close to Chatsworth House and Stanedge Golf Club, you are guaranteed a peaceful stay here. With a lovely country pub, the very popular wedding venue of the Peak Edge Hotel within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here.

Jan 16 – 23

R1,900 ZAR per night

Guest favorite

Loft in Ashover

4.97 out of 5 average rating, 150 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 with a drink or two in one of the friendly local pubs.

Nov 30 – Dec 7

R1,958 ZAR per night

Guest favorite

Cottage in Clay Cross

4.94 out of 5 average rating, 163 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.

Nov 28 – Dec 5

R2,123 ZAR per night

Guest favorite

Cottage in Holymoorside

4.97 out of 5 average rating, 219 reviews

Wasp Nest Cottage, Peak District

Sitting on the edge of the Peak District, a stone’s throw from open fields, woodland and moors - sits a 19th Century cosy mill worker’s cottage. Two pubs and a shop are within easy walking distance and Chatsworth House is a beautiful 7 mile wander over the hill. Marvel at the lovely centuries old tree slice, coffee table and huge slice of elm breakfast bar, enjoy chopping boards, pottery and soft furnishings from the local artisans - just some of the magic the Peak District has to offer.

Feb 7 – 14

R2,837 ZAR per night

Guest favorite

Guesthouse in Tansley

5.0 out of 5 average rating, 137 reviews

Oaks Edge View, Tansley, Matlock, Derbyshire

Oaks Edge View is a modern airy holiday home including Satellite TV, Wi-Fi, Large bedroom with a King-size bed and separate comfortable sofa bed. The bedroom can be set up to be used as a twin bedroom on request with a separate toilet upstairs. There is a well equipped kitchen, dining area, bathroom with a shower. A lockable lean to drying room for putting wet clothes and bicycles. There is off road parking and a garage available to store motor bikes. Oaks Edge View is 2 miles from Matlock.

Jun 13 – 20

R1,836 ZAR per night

Guest favorite

Cottage in Tibshelf

4.98 out of 5 average rating, 130 reviews

Lane End Cottage - cosy cottage with large garden.

16th century cosy stone cottage with large private garden, includes lounge, kitchen and separate dining room. Pretty sun room ideal for morning coffees. Two bedrooms, one twin, and one king size. Shower and toilet upstairs. Bed settee is in the dining room. Will easily sleep 6 but seating is limited in the lounge. The main bath and shower room is downstairs. There is a large lawn to the front of the property with off road parking, the rear garden is private and has use of a BBQ in summer.

Jul 30 – Aug 6

R3,047 ZAR per night

Guest favorite

Guest suite in Wingerworth

4.93 out of 5 average rating, 192 reviews

The Garden Room

The Annexe is self contained in the garden of our home in Wingerworth. Private entrance through small conservatory . Shower room , fridge, kettle, toaster , microwave. Cereals, bread, butter and preserves provided. Close to countryside and Peak District National Park . On drive parking. Bus stops nearby to Chesterfield and Derby with links by bus/train from Chesterfield Rail Station. Good local walks and Chatsworth Estate 20 minutes drive. Excellent Pub/Restaurant 5 minutes walk away.

Sep 25 – Oct 2

R1,021 ZAR per night

Guest favorite

Guest suite in Derbyshire

4.83 out of 5 average rating, 121 reviews

Annexe accommodation in Chesterfield

We have refreshed and given the Annexe a make over. The entrance has been spruced up and the bathroom given a new shower. Leading into the living area all newly painted and new accessories. The kitchen again given a new updated paint , the drawers under the hob replaced. A new styled bedroom with new wallpaper , and accessories an added freezer hidden in the wardrobe. Outside you have your own courtyard, which can be made private. Refurbished and private ready for you to enjoy.

Jan 4 – 11

R1,780 ZAR per night