Holiday cottage rentals near Chesterfield

15 rental properties match your search for Self-catering cottages and holiday accommodation in Chesterfield Derbyshire

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Price from £493
Next available 06/12 to 22/12/22
sleeps 2 - 4 guests 2 - 4
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1
5 star

2 bedroom Unique Self-Catering

Charming 2 bedroom pet-friendly chapel conversion near Carsington Water.

Facilities & Features: TV
1 of 400 listed cottages. See more properties from Sykes Cottages
Price from £3200
Next available 05/12 to 09/12/22
sleeps 7 - 14 guests 7 - 14
7 bedrooms 7
7 bathrooms 7
dog-friendly cottage, 2 dog(s) welcome2

7 bedroom Large Country House

Welcoming 7 en-suite bedroom holiday lodge with spacious and contemporary furnishings sleeping up to 14 adults (plus 2 children) and boasting a stunning location in the Peak District National Park with spectacular scenery and breath taking views over the Hope Valley.

Facilities & Features: Digital TVFree WifiGames room
Viewed 17 times recently.
Price from £655
Next available 02/01 to 07/01/23
sleeps 4 - 7 guests 4 - 7
3 bedrooms 3
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1
4 star

3 bedroom Farmstay

Family-friendly and pet-friendly holiday barn set next to stunning open countryside within the Peak District National Park and close to the town of Bakewell, this is a wonderfully relaxing place to stay which offers private use of both a hot tub and a sauna.

Facilities & Features: TVGames roomIndoor Hot TubSauna
1 of 400 listed cottages. See more properties from Sykes Cottages
Viewed 16 times recently.
Price from £387
Next available -
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
no dogs allowed
5 star

2 bedroom Barn Conversion

Lovely 2 bedroom stone-built barn conversion with a good quality interior and a location in a pretty little village close to Matlock and the Peak District National Park.

Facilities & Features: TV
1 of 400 listed cottages. See more properties from Sykes Cottages
Price from £1599
Next available -
sleeps 6 - 12 guests 6 - 12
6 bedrooms 6
6 bathrooms 6
no dogs allowed
3 star

6 bedroom Cottage

A former Bed & Breakfast, the fantastic detached house of Pig-Of-Lead rests at the foot of the village of Bonsall in Derbyshire.

Facilities & Features: TV
1 of 400 listed cottages. See more properties from Sykes Cottages
Price from £1450
Next available 05/12 to 09/12/22
sleeps 2 - 12 guests 2 - 12
6 bedrooms 6
5 bathrooms 5
dog-friendly cottage, 1 dog(s) welcome1
4 star

6 bedroom Large Country House

A fine holiday house in Matlock with views of nearby gardens, sleeping up to 12, ideal for large groups and special occasions, both family-friendly and pet-friendly.

Facilities & Features: Gold Award Winning CottageTVFree Wifi
Viewed 28 times recently.
Price from £180
Next available 30/12 to 16/01/23
no booking fee
sleeps 4 - 6 guests 4 - 6
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 2 dog(s) welcome2
5 star

2 bedroom Stone-Built Barn Conversion

Searching for a family cottage in the Peak District National Park? This charming pet-friendly cottage is ideal for family holidays, enjoys an idyllic setting next to fields and should be a hit with the kids with a garden with swings and sandpit where the children can play.

Facilities & Features: TVFree Wifi
Price from £4200
Next available 05/12 to 09/12/22
sleeps 10 - 22 guests 10 - 22
8 bedrooms 8
6 bathrooms 6
dog-friendly cottage, 2 dog(s) welcome2

8 bedroom Large Country House

8 bedroom country house with private swimming pool, hot tub, sauna, beautiful gardens and a BBQ lodge close to Matlock and the Peak District National Park, pet-friendly with 2 dogs welcome.

Facilities & Features: TVFree WifiGames roomOutdoor Hot TubSaunaHeated pool
1 of 5 listed cottages. See more properties from Derbyshire Holidays
Viewed 22 times recently.
Price from £806
Next available 06/12 to 16/12/22
sleeps 4 - 8 guests 4 - 8
4 bedrooms 4
2 bathrooms 2
no dogs allowed
5 star

4 bedroom Barn Conversion

This beautiful high quality 4 bedroom barn conversion lies within the gorgeous Peak District National Park and boasts a high quality interior and wonderful views over the surrounding Derbyshire countryside.

Facilities & Features: TV
1 of 400 listed cottages. See more properties from Sykes Cottages
Price from £527
Next available 09/12 to 23/12/22
sleeps 3 - 6 guests 3 - 6
3 bedrooms 3
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1
4 star

3 bedroom Cottage

Field House in Swanwick, Derbyshire is a remarkable, detached holiday home in attractive surroundings.

This owner/agency is showing availability but has not provided full pricing information.
Price from £1700
Next available 05/12 to 18/08/23
sleeps 2 - 10 guests 2 - 10
5 bedrooms 5
4 bathrooms 4
no dogs allowed

5 bedroom Large Holiday House to rent

Sleeps 10 holiday house with warm bubbly outdoor private hot tub and games room, just outside of the Peak District National Park.

Facilities & Features: TVFree WifiGames roomOutdoor Hot Tub
This owner/agency is showing availability but has not provided full pricing information.
Price from £2200
Next available 05/12 to 20/01/23
sleeps 4 - 10 guests 4 - 10
5 bedrooms 5
4 bathrooms 4
no dogs allowed

5 bedroom Stone-Built Cottage

No pets 4 bedroom holiday home in a tranquil village setting near Bakewell and the Peak District National Park, with the added luxury of a bubbly outdoor hot tub and games room.

Facilities & Features: TVFree WifiGames roomOutdoor Hot Tub
1 of 3 listed cottages. See more properties from Luxury Holiday Homes Derbyshire
Total maximum capacity across all listed cottages: 15 people.
Viewed 16 times recently.
This owner/agency is showing availability but has not provided full pricing information.
Price from £580
Next available 05/12 to 23/12/22
sleeps 1 - 3 guests 1 - 3
2 bedrooms 2
2 bathrooms 2
no dogs allowed

2 bedroom Rural Retreat

Idyllic sleeps 3 rural retreat in a superb country location and with beautiful views over the Derwent Valley, situated just outside of the Peak District National Park and close to Matlock.

Facilities & Features: Free Wifi
1 of 3 listed cottages. See more properties from Luxury Holiday Homes Derbyshire
Total maximum capacity across all listed cottages: 15 people.
Sorry, this owner/agency has not provided availability and full price information.
Price from £473
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 2 dog(s) welcome2
4 star

2 bedroom Bungalow

Comfortable 2 bedroom country cottage nestled in 3 acres of tranquil gardens, discover the best of Nottinghamshire close by with day trips to the riverside town of Newark-on-Trent, Clipstone Forest and Sherwood Forest to name just a few attractions.

Facilities & Features: TVFree Wifi
Viewed 9 times recently.
Sorry, this owner/agency has not provided availability and full price information.
Price from £350
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
dog-friendly cottage, 2 dog(s) welcome2

1 bedroom Romantic Retreat

Beautiful romantic retreat for 2, in the heart of Two Dales, just a short drive from the Peak District National Park.

Facilities & Features: TVFree Wifi
1 of 3 listed cottages. See more properties from Luxury Holiday Homes Derbyshire
Total maximum capacity across all listed cottages: 15 people.
* Price quoted is not inclusive of any applicable booking fees or local charges.

Please click on any images shown of self-catering holiday accommodation near Chesterfield, Derbyshire, to view details of the accommodation. The town of Chesterfield lies to the east of the Peak District and could be considered the eastern gateway to the national park via the Chatsworth Road. It is a sizeable market town with a good shopping centre. The town's crooked spire is one of the landmarks that signifies an approach to the national park.

Book a good quality country cottage near Chesterfield, just outside the borders of the national park in holiday rentals that should be at a lower rental price. There are plenty of things for people on holiday to do in Chesterfield and we all enjoy a little shopping, meals out and a night at the cinema.The Chatsworth Road leading west from Chesterfield takes you directly into the Chatsworth Park.

The holiday accommodation

A summary of the self-catering accommodation with about 5 miles of Chesterfield is shown. Pet-friendly cottages are marked if you plan to bring your dog. Click on the cottages that match your requirements to find out more about each one and a gallery of photographs.

Every holiday rental shown is managed by a genuine and professional company. All properties offer a high standard of attractive accommodation that would please most. Find budget holiday homes, also luxurious large houses with a swimming pool or tennis court that might appeal to bigger groups for a celebration or hen or stag weekend.

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