A village with houses on a hillside, surrounded by trees and open fields.

Winster Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winster holiday rentals

A cozy living room with a black leather sofa, a wooden coffee table, and a bookshelf.

1. The Dell

The Dell
2.0 star property
Matlock
10.0 out of 10, Exceptional, (1 review)
"Went for a nice weekend away, took a little working out where it was located, for help, left at the green then left down the tracks :) House was in prestine condition was a lovely stay"
United Kingdom
Shane
The price is AU$693
includes taxes & fees
30 Oct - 31 Oct
The Dell
A stone house with a conservatory, a well-maintained lawn, and surrounding greenery.

2. Ivy Cottage

Ivy Cottage
3.5 star property
Matlock
The price is AU$883
includes taxes & fees
30 Oct - 31 Oct
Ivy Cottage
A stone building with multiple windows and a door, surrounded by stone walls and greenery.

3. Daisy Cottage

Daisy Cottage
3.5 star property
Matlock
The price is AU$953
includes taxes & fees
16 Oct - 17 Oct
Daisy Cottage
A stone building with a blue door labeled "The Hayloft."

4. The Hayloft

The Hayloft
3.5 star property
Matlock
The price is AU$623
includes taxes & fees
14 Oct - 15 Oct
The Hayloft
A living room with a sofa, a coffee table with croissants, a TV, and a staircase.

5. Gratton Grange Farm Holiday Cottage

Gratton Grange Farm Holiday Cottage
3.0 star property
Bakewell
9.4 out of 10, Exceptional, (63 reviews)
"Great peaceful location. Cottage has everything you need for an enjoyable stay."
United Kingdom
Richard
The price is AU$256
includes taxes & fees
12 Oct - 13 Oct
Gratton Grange Farm Holiday Cottage
A cozy living room with a leather sofa, a wooden table, and a red rug. There is a window with a stained glass design and a round skylight.

6. Andlestone

Andlestone
3.0 star property
Matlock
10.0 out of 10, Exceptional, (1 review)
"Would recommend - beautiful, spacious and clean."
United Kingdom
Rebecca
The price is AU$1,048
includes taxes & fees
30 Oct - 31 Oct
Andlestone
A stone house with a wooden bench in front, a car parked nearby, and a stone wall in the background.

7. Robin Hood Tower

Robin Hood Tower
3.0 star property
Matlock
10.0 out of 10, Exceptional, (15 reviews)
"This is a wonderfully quirky and unique place to stay. The accommodation is just perfect. Hosts Steve and Elaine have created a tranquil and idyllic tiny retreat at Robin Hood Tower. Comms were great and Steve showed us around, sharing local history and top tips for our trip. Canal side walks were glorious. A magical stay."
United Kingdom
Heidi
The price is AU$399
includes taxes & fees
12 Oct - 13 Oct
Robin Hood Tower
A room with a round wooden table, a lamp, and a vase with flowers.

8. Family Home | River Derwent | Hot tub | 10 guests

Family Home | River Derwent | Hot tub | 10 guests
Darley Bridge
9.8 out of 10, Exceptional, (50 reviews)
"A family get together so 9 of us and our dogs. The house is so spacious and in such an amazing location. We visited during the heatwave in May so we spent a lot of time in the river. There is everything you need and the beds are really comfy. Would highly recommend and would definitely revisit."
United States
Linda P.
The price is AU$1,820
includes taxes & fees
20 Oct - 21 Oct
Family Home | River Derwent | Hot tub | 10 guests
A four-poster bed with a wooden headboard, two bedside tables, and a window with curtains.

9. 3 bedroom accommodation in Hartington

3 bedroom accommodation in Hartington
Hartington
The price is AU$612
includes taxes & fees
29 Oct - 30 Oct
3 bedroom accommodation in Hartington
A stone building with a wooden picnic table and benches, surrounded by lush greenery and potted plants.

10. Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne

Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne
Ashbourne
9.6 out of 10, Exceptional, (181 reviews)
"A true gem! Thoroughly enjoyed our stay here and will definitely be booking again. Wonderful!"
United States
Debbie W.
The price is AU$409
includes taxes & fees
12 Oct - 13 Oct
Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne
A narrow gravel path flanked by lush greenery and stone buildings with blue shutters.

11. Rose Cottage - Cosy Cottage in Millers Dale

Rose Cottage - Cosy Cottage in Millers Dale
3.0 star property
Buxton
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place to stay. I will definitely come back in the future."
United States
HYERYEON
The price is AU$352
includes taxes & fees
15 Oct - 16 Oct
Rose Cottage - Cosy Cottage in Millers Dale
A window with a view of a rocky landscape and a flowing stream.

12. Historic Water Mill in the heart of the Peak District

Historic Water Mill in the heart of the Peak District
Millers Dale
10.0 out of 10, Exceptional, (14 reviews)
"Me and my friends had a lovely weekend in this gorgeous apartment. It is nestled in the most beautiful valley and has everything you need to be able to enjoy yourself completely Had a fabulous time"
United Kingdom
Lucy C.
The price is AU$418
includes taxes & fees
11 Oct - 12 Oct
Historic Water Mill in the heart of the Peak District
A modern hotel lobby with a reception desk, seating area, and a door leading to the lift, stairs, and locker room.

13. Rock Mill Retreat

Rock Mill Retreat
Stoney Middleton
10.0 out of 10, Exceptional, (1 review)
"Amazing retreat in the heart of the Peak District. Spotless clean, highest quality kitchen appliances, wellness tech, sauna for private use. Quiet and modern. Loved it!"
United Kingdom
Daniel
The price is AU$343
includes taxes & fees
5 Nov - 6 Nov
Rock Mill Retreat
A patio with a stone table and chairs, surrounded by a wooden fence and potted plants.

14. Tranquil Period Cottage On The Edge Of Tideswell, 5 mins stroll to centre.

Tranquil Period Cottage On The Edge Of Tideswell, 5 mins stroll to centre.
Tideswell
8.8 out of 10, Excellent, (21 reviews)
"Perfect property for a family gathering. Lots of space inside and for dining. Parking was great outside the back of the house for all three cars each day."
United Kingdom
Alastair H.
The price is AU$619
includes taxes & fees
11 Oct - 12 Oct
Tranquil Period Cottage On The Edge Of Tideswell, 5 mins stroll to centre.
A modern kitchen with built-in appliances, a dining area with a wooden table and chairs, and a clock on the wall.

15. Brewers Cottage - sleeps 2 guests in 1 bedroom

Brewers Cottage - sleeps 2 guests in 1 bedroom
Foolow
10.0 out of 10, Exceptional, (6 reviews)
"Ideal for us on a short visit to family with fog in tow. Foolow a lovely village with great pub and stunning views"
United States
marcus s.
The price is AU$262
includes taxes & fees
11 Oct - 12 Oct
Brewers Cottage - sleeps 2 guests in 1 bedroom
A white metal bench with a tray table and a bottle of wine, placed against a stone wall with a window.

16. The Hill

The Hill
3.0 star property
Matlock
9.4 out of 10, Exceptional, (6 reviews)
"Cute little cottage perfect for a couple looking to explore the Peak District. "
United Kingdom
India
The price is AU$527
includes taxes & fees
14 Oct - 15 Oct
The Hill
A house with a brick exterior, a glass door, and a small balcony.

17. Hayeswood Lodge Luxury Accommodation

Hayeswood Lodge Luxury Accommodation
3.5 star property
Ilkeston
10.0 out of 10, Exceptional, (35 reviews)
"Great place - very clean and a lovely little breakfast"
United Kingdom
Ian
The price is AU$282
includes taxes & fees
19 Oct - 20 Oct
Hayeswood Lodge Luxury Accommodation
A cozy cabin interior with a bed, a sofa, a fireplace, and a window.

18. Bertie's Retreat - sleeps 2 guests in 1 bedroom

Bertie's Retreat - sleeps 2 guests in 1 bedroom
Foolow
9.2 out of 10, Wonderful, (5 reviews)
"Had fabulous stay at Bertie’s retreat …hot tub was amazing too . Only thing I missed was an oven ! "
United Kingdom
Julia H.
The price is AU$253
includes taxes & fees
11 Oct - 12 Oct
Bertie's Retreat - sleeps 2 guests in 1 bedroom
A compact kitchen with a microwave, sink, and dark cabinets. There's a wooden door leading to another room and a sofa in the corner.

19. Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom

Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom
Foolow
10.0 out of 10, Exceptional, (5 reviews)
"Enjoyable stay"
United Kingdom
Michael
The price is AU$218
includes taxes & fees
12 Oct - 13 Oct
Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom
A dining table with plates, croissants, wine glasses, and a vase with yellow flowers.

20. Britannia Chambers

Britannia Chambers
3.0 star property
Leek
8.4 out of 10, Very good, (15 reviews)
"The property was cold and the device to set the temperature seemed to be out of battery. It was somewhat hard to find, and when we entered there was a vacuum cleaner sitting in the hallway. Parking can be hard to find, and the owners' emails seemed to be automatic and not responsive."
Canada
Andrew
The price is AU$291
includes taxes & fees
12 Oct - 13 Oct
Britannia Chambers
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winster Hotel Reviews

easyHotel Sheffield

easyHotel Sheffield

10/10 Excellent
"Small room but clean & comfortable. Excellent location in city centre, right next to a tram stop, supermarkets & wetherspoons!"
merrick 3-night trip
Posted 1 hour ago
easyHotel Sheffield

Find out more about Winster

Everything you need to know about Winster holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winster holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winster holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winster holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winster. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winster holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winster holiday rentals we have selected for you start as low as AU$106 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winster rentals

At Expedia, we put the best Winster holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winster rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winster holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winster. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winster?

Yes, there are holiday rentals close to the most popular sights in Winster, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winster has to offer?

Old Nags Head: This holiday home rental outside of Winster comes with free WiFi so that you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave and kitchenware.

How many holiday rentals are there in Winster?

Choose from 7 Expedia holiday rentals in Winster for a memorable holiday.

What can I see and do in Winster?

Explore the area and family-friendly sights such as Gulliver's Kingdom, or get out into nature at a spot like Peak District National Park. Heights of Abraham Cable Car Station and Peak District Mining Museum & Temple Mine are a couple of places you'll find in the wider area.

What are holiday rentals like in Winster?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winster. Holiday rentals offer amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.