Winster Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Winster holiday rentals

Property grounds
The Dell

The Dell

The Dell
2.0 star property
Matlock
10.0 out of 10, Exceptional, (1)
"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 HK$3,830
HK$3,830 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Dell
Property grounds
Hill Cottage

Hill Cottage

Hill Cottage
3.5 star property
Matlock
The price is HK$4,387
HK$5,264 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hill Cottage
Interior
Ivy Cottage

Ivy Cottage

Ivy Cottage
3.5 star property
Matlock
The price is HK$4,066
HK$4,879 total
includes taxes & fees
5 Jan - 6 Jan 2026
Ivy Cottage
Interior
Daisy Cottage

Daisy Cottage

Daisy Cottage
3.5 star property
Matlock
The price is HK$4,119
HK$4,943 total
includes taxes & fees
5 Jan - 6 Jan 2026
Daisy Cottage
Private kitchen
The Hayloft

The Hayloft

The Hayloft
3.5 star property
Matlock
The price is HK$2,867
HK$3,440 total
includes taxes & fees
10 Jan - 11 Jan 2026
The Hayloft
Fridge, electric kettle, toaster, cookware/dishes/utensils
East Bank Cottage

East Bank Cottage

East Bank Cottage
2.5 star property
Matlock
The price is HK$3,174
HK$3,809 total
includes taxes & fees
2 Jan - 3 Jan 2026
East Bank Cottage
Lounge
Houseboat Hotels

Houseboat Hotels

Houseboat Hotels
3.0 star property
Sheffield
9.4 out of 10, Exceptional, (61)
"Another excellent trip on the houseboat. Love this hotel - great location, fabulous accommodation. Why stay in a regular hotel when you can stay here!"
United Kingdom
Wendy
The price is HK$1,267
HK$1,521 total
includes taxes & fees
20 Jan - 21 Jan 2026
Houseboat Hotels
Interior
Ash House

Ash House

Ash House
3.5 star property
Stoke-on-Trent
10.0 out of 10, Exceptional, (6)
"Can't fault anything about the stay. The cottage, the facilities, the cleanliness, the communication and the value were all absolutely impeccable."
United Kingdom
Andrew
The price is HK$5,037
HK$6,045 total
includes taxes & fees
3 Jan - 4 Jan 2026
Ash House
Private kitchen
2-bed House in Chesterfield Free Parking Garden

2-bed House in Chesterfield Free Parking Garden

2-bed House in Chesterfield Free Parking Garden
2.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
The price is HK$908
HK$1,216 total
includes taxes & fees
1 Jan - 2 Jan 2026
2-bed House in Chesterfield Free Parking Garden
Exterior
Hayeswood Lodge Luxury Accommodation

Hayeswood Lodge Luxury Accommodation

Hayeswood Lodge Luxury Accommodation
3.5 star property
Ilkeston
10.0 out of 10, Exceptional, (34)
"Really friendly and helpful hosts and the chalets are finished to a very high standard. Lovely and peaceful with a really comfy bed. Didn’t find fault with anything during my stay and would definitely recommend to others and stay again if I’m in the area. 10/10"
United Kingdom
Nick
The price is HK$1,197
HK$1,437 total
includes taxes & fees
12 Jan - 13 Jan 2026
Hayeswood Lodge Luxury Accommodation
Exterior
Hidden Gem of Sheffield

Hidden Gem of Sheffield

Hidden Gem of Sheffield
2.5 star property
Nether Edge
7.0 out of 10, Good, (2)
"The property itself was ok but it is joined to a building site and all you hear is stihl saws loud music and shouting and swearing from the builders. The 9 pm noise curfew is a joke, bangra until the early hours. Stay Angels were no help at the point of complaint, nothing we can do was their mantra."
United Kingdom
Neil
The price is HK$754
HK$1,522 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hidden Gem of Sheffield
Private kitchen
Field House

Field House

Field House
3.5 star property
Alfreton
10.0 out of 10, Exceptional, (3)
"Good location for visiting Derbyshire and the Peak District "
United Kingdom
john
Field House
37-inch Smart TV with cable channels, TV
Spacesavers

Spacesavers

Spacesavers
3.5 star property
Sheffield City Centre
8.2 out of 10, Very good, (55)
"Property was brilliant and spacious, great for a couple get away."
United Kingdom
Cameron
The price is HK$551
HK$662 total
includes taxes & fees
5 Jan - 6 Jan 2026
Spacesavers
Flat-screen TV
Britannia Chambers

Britannia Chambers

Britannia Chambers
3.0 star property
Leek
8.4 out of 10, Very good, (15)
"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 HK$1,613
HK$1,935 total
includes taxes & fees
1 Jan - 2 Jan 2026
Britannia Chambers
Desk, laptop workspace, soundproofing, free WiFi
Three Cranes Serviced Apartments

Three Cranes Serviced Apartments

Three Cranes Serviced Apartments
3.5 star property
Sheffield City Centre
8.4 out of 10, Very good, (127)
"Great place to stay"
United Kingdom
Graham
Three Cranes Serviced Apartments
Private kitchen
The Nest

The Nest

The Nest
3.5 star property
Sheffield City Centre
6.8 out of 10, (16)
"Excellent location, specious flat, will definitely book again!"
United Kingdom
Magdalena
The Nest
Shared kitchen
Robin Hood Tower

Robin Hood Tower

Robin Hood Tower
3.0 star property
Matlock
10.0 out of 10, Exceptional, (11)
"Lovely location with everything we needed for a very peaceful vacation. The hosts were very welcoming and gave us a little tour of the grounds and lots of information about the area."
United Kingdom
Judith
The price is HK$1,836
HK$2,203 total
includes taxes & fees
8 Jan - 9 Jan 2026
Robin Hood Tower
Private kitchen
Arbourfield Lodge

Arbourfield Lodge

Arbourfield Lodge
2.5 star property
Derby
8.0 out of 10, Very good, (3)
"Lovely accommodation! Very clean and excellently equiped ! "
United Kingdom
Elaine
Arbourfield Lodge
Terrace/patio
Derby City Centre Apartment With Roof Top Hot Tub

Derby City Centre Apartment With Roof Top Hot Tub

Derby City Centre Apartment With Roof Top Hot Tub
3.0 star property
Derby
10.0 out of 10, Exceptional, (2)
"Lovely stay again xx"
United Kingdom
Susan
The price is HK$1,705
HK$2,235 total
includes taxes & fees
1 Jan - 2 Jan 2026
Derby City Centre Apartment With Roof Top Hot Tub
Interior
3 Old Hall Cottages

3 Old Hall Cottages

3 Old Hall Cottages
3.5 star property
Bakewell
10.0 out of 10, Exceptional, (1)
"Beautiful property, everything you could want or need is provided for you. Very comfortable & cozy. Nice location for a few days away thank you will come again "
United Kingdom
Derek
The price is HK$3,749
HK$4,499 total
includes taxes & fees
3 Jan - 4 Jan 2026
3 Old Hall Cottages
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

DoubleTree by Hilton Sheffield City

DoubleTree by Hilton Sheffield City

10/10 Excellent
"Spacious roooms, comfy beds, nice clean bathroom"
Rebecca 1-night trip
Posted 5 days ago
DoubleTree by Hilton Sheffield City

Find out more about Winster

Search for holiday rentals in Winster on Expedia! You can easily find your home rentals, villas, holiday apartments in Winster using one of the methods below:

  • View our selection of featured holiday rentals in Winster
  • Use the map to find apartments and other holiday homes in the Winster neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winster while they last

Look no further and take a look at our great range of rental properties in Winster!

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?

Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly: This holiday home rental outside of Winster offers a private balcony, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Winster?

Choose from 5 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 The Grand Pavilion, Matlock Bath 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.