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Self catering holiday cottages in Winster Derbyshire

Showing all properties across the UK. Select a destination from the list to refine your search.
33 holiday rentals
Family-Friendly
Viewed 20 times recently.
Winster 8 miles away

Hillside Croft,

Biggin, Ashbourne, Derbyshire, England
sleeps  16 sleeps 16
5 bedrooms 5 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

5 bedroom large holiday house with private hot tub, set on edge of Peak District National Park, close to both Ashbourne and Carsington Water.

ensuite bedroom(s) garden views
Facilities, Features & Awards:
smart TVdishwasher in kitchenmicrowave in kitchenoutdoor hot tub accessfree Wifienclosed gardenwood burning stovefireplaceBBQfirepitParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £2150
Next available: 04 Jan - 7 nights
Online Booking Available
Viewed 27 times recently.
Winster 3 miles away

Two Owls Lodge,

Two Dales, Derbyshire, England
sleeps  3 sleeps 3
2 bedrooms 2 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

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.

valley views near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifiPatio Gardenwood burning stovefireplaceParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £595
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Online Booking Available
Viewed 30 times recently.
Winster 3 miles away

The Haven - Luxury Sheltered Hot Tub & Games Room,

Two Dales, Derbyshire, England
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
4 bathrooms 4 bathrooms
no dogs allowed No pets
family friendly family friendly

No pets 5 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.

ensuite bedroom(s) countryside views over fields and farmlands
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree Wifienclosed gardenBBQParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £2200
Next available: 20 Dec - 3 nights
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Online Booking Available
Viewed 26 times recently.
Winster 3 miles away

The Escape,

Two Dales, Derbyshire, England
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
4 bathrooms 4 bathrooms
no dogs allowed No pets
family friendly family friendly

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

ensuite bedroom(s) countryside views over fields and farmlands
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accessfree WifigardenBBQParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £2200
Next available: 03 Jan - 7 nights
book online online booking
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Family-Friendly
Viewed 32 times recently.
Winster 12 miles away

Ebenezer Chapel,

Milford, Derbyshire, England
sleeps  20 sleeps 20
8 bedrooms 8 bedrooms
5 bathrooms 5 bathrooms
 1 dog welcome  1 dog allowed
family friendly family friendly

With a riverside location and river views, this unique chapel conversion in Milford could be the ideal place to holiday with friends or family close to the Peak District, and the on site sauna suite helps to make it a great place to relax and unwind too.

ground floor bedroom river views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchensaunafree Wifigardenwood burning stoveBBQ
Sorry, this owner/agency has not provided availability information.
7 nights from £1695
Special Offer: 09 Jan - 3 nights
Online Booking Available
Viewed 26 times recently.
Winster 12 miles away

Hagg Hill Hall,

Chesterfield, Derbyshire, England
sleeps  22 sleeps 22
8 bedrooms 8 bedrooms
6 bathrooms 6 bathrooms
 2 dogs welcome  2 dogs welcome
family friendly family friendly

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.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomoutdoor hot tub accesssaunaonsite heated poolfree Wifienclosed gardenfireplaceBBQParking
Sorry, this owner/agency has not provided availability information.
7 nights from £4700
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Online Booking Available
Viewed 15 times recently.
Winster 9 miles away

Turpins Cottage,

Belper, Derbyshire, England
sleeps  20 sleeps 20
9 bedrooms 9 bedrooms
5 bathrooms 5 bathrooms
 2 dogs welcome  2 dogs welcome
family friendly family friendly

Sleeps 20, 9 Bedroom Rural Holiday House with Games Room with Pool Table, near Belper and the Peak District Turpins cottage could be a stunning location for your next holiday, situated on a pretty farm setting, where you can escape from busy city or town life with your friends and family.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomfree WifigardenBBQParking
Sorry, this owner/agency has not provided availability and full price information.
7 nights from £2100
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Winster 12 miles away

The Barn at Hill House,

Leek, Staffordshire, England
sleeps  8 sleeps 8
4 bedrooms 4 bedrooms
3 bathrooms 3 bathrooms
 1 dog welcome  1 dog allowed
family friendly family friendly

Beautiful 4 bedroom dog-friendly barn conversion with stunning country views, ideal for exploring the Peak District National Park.

near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenBBQParking
7 nights from £914
Next available: 13 Feb - 7 nights
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Winster 11 miles away

Manor House,

Chesterfield, Derbyshire, England
sleeps  10 sleeps 10
5 bedrooms 5 bedrooms
5 bathrooms 5 bathrooms
no dogs allowed No pets
family friendly family friendly

Discover luxurious living at Manor House, a dog-friendly, detached cottage in Chesterfield, Derbyshire, sleeping ten with a private gym, woodburning stove, and children's play area; perfect for exploring the stunning Peak District's natural beauty.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenfireplaceParking
7 nights from £2038
Next available: 04 Jan - 7 nights
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Online Booking Available
Viewed 18 times recently.
Winster 2 miles away

Cow Barn, Peak District National Park,

Alport, Derbyshire, England
sleeps  8 sleeps 8
4 bedrooms 4 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

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 & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree Wifigardenwood burning stovefireplaceParking
7 nights from £821
Next available: 30 Jan - 7 nights
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Winster 0 miles away

Winster Hall,

Matlock, Derbyshire, England
sleeps  10 sleeps 10
7 bedrooms 7 bedrooms
5 bathrooms 5 bathrooms
 dog-friendly cottage
family friendly family friendly

Winster Hall in Derbyshire's Peak District is a dog-friendly, Grade II listed retreat sleeping 16, featuring original architectural beauty, expansive gardens, and convenient access to Matlock and Bakewell, with captivating village street views.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenfireplaceBBQParking
7 nights from £2278
Next available: 16 Jan - 7 nights
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Online Booking Available
Viewed 27 times recently.
Winster 8 miles away

Church Barn, Peak District ,

Fenny Bentley, Derbyshire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
no dogs allowed No pets

Romantic barn conversion with tranquil views, set in the Peak District National Park, close to Ashbourne, the Tissington Trail and Dovedale.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVmicrowave in kitchenfree Wifigardenwood burning stoveParking
7 nights from £359
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Online Booking Available
Viewed 17 times recently.
Winster 10 miles away

Manifold Cottage,

Leek, Staffordshire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
 dog-friendly cottage
family friendly family friendly

Charming Grindon cottage in Staffordshire, West Midlands, offering stunning Peak District countryside views, sleeps two, features a cosy open-plan living area, and a serene enclosed garden – perfect for walkers and cyclists; sorry, no pets.

ground floor bedroom near local pub
Facilities, Features & Awards:
Parkinggarden
7 nights from £338
Next available: 29 Dec - 7 nights
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Online Booking Available
Viewed 30 times recently.
Winster 5 miles away

Orchard View Dogs-Welcome Cottage, Peak District National Park,

Parwich, Derbyshire, England
sleeps  9 sleeps 9
4 bedrooms 4 bedrooms
3 bathrooms 3 bathrooms
 1 dog welcome  1 dog allowed
family friendly family friendly

Idyllic 4 bedroom English country cottage with exposed wooden beams, wood-burning stove and a very comfortable interior and a pet-friendly policy, also features a romantic four poster bed in one of the bedrooms, as well as a superb location within the Peak District National Park and a Wendy House for keeping younger visitors entertained.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomfree Wifigardenwood burning stovefireplaceParking
7 nights from £657
Next available: 20 Dec - 7 nights
book online online booking
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Winster 17 miles away

Midfeather Cottage,

Edale, Derbyshire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
no dogs allowed No pets
family friendly family friendly

Nestled in Derbyshire's stunning Peak District, this charming, dog-friendly stone barn sleeps 4, offering breathtaking countryside views, original features, and a shared paddock, just a stroll from Edale village and the Pennine Way.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenfree WifigardenParking
7 nights from £485
Next available: 03 Jan - 7 nights
book online online booking
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* Price quoted is not inclusive of any applicable booking fees or local charges.

Located within the Peak District Park is the quaint village of Winster in Derbyshire. With stone-built cottages, tree lined streets and a setting by the hills of the Peak District this is a beautiful part of England with plenty to recommend it for country cottage holidays.


What Winster offers for Cottage Breaks

Britain’s National Parks are renowned for their beautiful greenery and generous open spaces and the Peak District is no exception to the rule. Comprised of the White Peak and the Dark Peak, which each has its own unique landscape, the Peak District draws in keen walkers and hikers season after season. It is also a great place for keen photographers with its wild natural beauty.

When it comes to relaxing and taking it easy whilst on a cottage break, the Peak District is dotted with numerous pretty towns and villages where you can stop for a reviving cup of tea or refreshing pint. Whatever takes your fancy, you can be assured that the Peak District caters for most tastes.

There are plenty of places to visit whilst enjoying a cottage holiday in Winster both within the national park and outside it.  The National Trust country estate and impressive mansion house of Chatsworth is less than 10 miles away and is a stunning place which offers amazing views over the local landscape. Entrance is of course free to National Trust members and with a pet-friendly policy applying to the grounds, this is a great place for those with dogs.

More stunning scenery can be found at the Heights of Abraham at Matlock Bath around 7 miles from Winster. With woodlands, caverns and amazing views on offer plus a ride on a cable car, the Heights of Abraham makes for a great day out whilst on a self-catering break.

All in all the Peak District has lots to recommend it whether you are planning a romantic getaway or a family holiday. For peace and tranquillity rural country cottages could be a great choice. Whatever you choose, Country Cottages Online features a fantastic collection of good quality cottages.

Whether you choose to book a holiday cottage in Winster, an apartment, a lodge or another type of self-catering holiday accommodation, we hope you have your best holiday yet in Derbyshire.

Frequently Asked Questions about Winster

The best places to stay depend on your preferences, interests and the type of accommodation that best suits you. Country Cottages Online features a great selection of good quality rentals.
See our selection of pet-friendly rentals in Winster, or use the filters to refine your search.
See our selection of lodges and cabins in Winster, Derbyshire.
Read the description of Winster to find out ideas and tips on the best things to see and do. Also see our area guides for more information on what Derbyshire has to offer for holidaymakers.

Winster Holiday Rental Searches