Chesterfield District Vacation Rentals from CA $125: Short-Term Rentals for 2026

A town square with a prominent church steeple, a clock tower, and traditional half-timbered buildings.

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Our top choices for Chesterfield District vacation rentals

1. The Old School House

Brimington

CA $326 total

includes taxes & fees

Oct 20 - Oct 21

A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

2. Cedar Cottage

Chesterfield

CA $746 total

includes taxes & fees

Oct 30 - Oct 31

A sunlit room with a large window, a sofa, a table, and a potted plant.

3. Overton

Chesterfield

CA $1,082 total

includes taxes & fees

Nov 1 - Nov 2

A hot tub under a wooden pergola with a stone wall and greenery in the background.

4. Cherry Tree Cottage

Chesterfield

Lorraine

CA $1,230 total

includes taxes & fees

Oct 24 - Oct 25

A living room with a sofa, a coffee table with croissants, a TV, and a staircase.

5. Gratton Grange Farm Holiday Cottage

Bakewell

Irene

CA $254 total

includes taxes & fees

Oct 20 - Oct 21

A modern kitchen with white cabinets, a stainless steel range hood, a washing machine, and a dining area with a glass table set for two.

6. No2

Mansfield

J M

CA $300 total

includes taxes & fees

Oct 25 - Oct 26

A man holding a wine glass at a table with various bottles and glasses of wine.

7. Rock Mill Retreat

Stoney Middleton

Daniel

CA $331 total

includes taxes & fees

Nov 17 - Nov 18

A room with exposed wooden beams, a flat-screen TV mounted on the wall, and three hanging light bulbs.

8. Three Cranes Serviced Apartments

Sheffield City Centre

Graham

CA $125 total

includes taxes & fees

Nov 19 - Nov 20

A dining area with a wooden table set for four, two candles, and a view of the kitchen and living area.

9. 2 Car Parking Spaces, Pet Friendly, Central Bakewell In The Peak District

Bakewell

AKBAR

CA $603 total

includes taxes & fees

Oct 23 - Oct 24

A stone building with a sign reading "Kingfisher Lodge."

10. Stone built self-catering lodge in stunning location

Froggatt

Michelle C.

CA $209 total

includes taxes & fees

Oct 20 - Oct 21

A hotel room with a bed, a window with curtains, a radiator, and a door leading to a bathroom.

11. Kingfield Boutique Hotel

Nether Edge

Caroline

CA $136 total

includes taxes & fees

Oct 21 - Oct 22

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.

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

Foolow

Michael

CA $216 total

includes taxes & fees

Oct 21 - Oct 22

A narrow gravel path flanked by lush greenery and stone buildings with blue shutters.

13. Rose Cottage - Cosy Cottage in Millers Dale

Buxton

HYERYEON

CA $349 total

includes taxes & fees

Nov 3 - Nov 4

A stone building with a sloped roof, a paved driveway, and a bench outside.

14. The Rumblings 1

Dronfield

" Country road unamed , Speeders 50 / 60 mph plus used as a rat run . Not safe for walking out with dog or young child . Property nice but dog has to go too up side of road as no garden . Too fast traffic passing , Settees 2 seaters too small not comfortable and I’m a size 14 , this has been mentioned in comments book a few years ago . Info leaflets over 2/3 yrs old so prices out of date . For pub menus need binned despite Everyone does not go on the internet looking for everything on it your...

Joy

CA $659 total

includes taxes & fees

Nov 1 - Nov 2

A cozy room with a bed, a sofa, a desk, and a window with curtains.

15. Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom

Foolow

Michael

CA $218 total

includes taxes & fees

Oct 20 - Oct 21

A modern living room with a glass dining table, black and white chairs, a black sofa with teal cushions, and a yellow rug.

16. No 11

Mansfield

CA $300 total

includes taxes & fees

Nov 1 - Nov 2

17. Old Nags Head

Hope Valley

Kai

CA $267 total

includes taxes & fees

Nov 4 - Nov 5

A modern kitchen with built-in appliances, a dining area with a wooden table and chairs, and a clock on the wall.

18. Brewers Cottage - sleeps 2 guests in 1 bedroom

Foolow

marcus s.

CA $260 total

includes taxes & fees

Oct 25 - Oct 26

A spacious dining area with multiple tables and chairs, large windows, and a potted plant.

19. Sheffield Metropolitan by Belvilla - Standard Double Room

Sheffield

CA $73 total

includes taxes & fees

Oct 29 - Oct 30

A small, modern bedroom with a single bed, a small table, and a window with a view of a building.

20. Spacious 5BR Sheffield Home | City Access & WiFi

Sheffield

CA $944 total

includes taxes & fees

Nov 4 - Nov 5

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Top Chesterfield District Hotel Reviews

voco Sheffield by IHG

8/10 Good

"Hotel room nice size and clean. The hotel location is perfect and central plus a short walk to the train station. Dining area being renovated so breakfast was at piccolino for £16 a head but not loads of choice. Not many Tea bags or coffee put in room and even though moisturiser was asked to be topped up twice it never was."

Leonardo Hotel Sheffield

8/10 Good

"We had a two day stay in a family room. Very clean and was ready ahead of check in . Very good customer service at desk. We didn’t manage to get hotel parking but there were plenty of car parking facilities very close to hotel. Breakfast was more than adequate and seemed to cater for all tastes. Overall a very good stay"

Novotel Sheffield Centre

10/10 Excellent

"We had a 2 night stay at the Sheffield Novotel and really enjoyed our stay. Staff were helpful, room was clean and large. We accidentally booked an accessible room so the shower was not positioned as it would be in a regular room. We had breakfast one morning and the lady in charge helped me with the gluten free items. We used the pool and steam room for an hour during our stay which was a pleasant addition. The hotel is literally at the back of the Wingter gardens so we could easily access the city centre. It is also a very short walk from the railway station too."

Radisson Blu Hotel, Sheffield

8/10 Good

"The receptionist I dealt with was charming - she created a great first impression. The roof top restaurant and bar was ok the menus were a bit battered and in need of replacing. The room was a good size, clean with some nice extras like the shoe shine sponge, and grooming kit. Location was excellent and Sheffield is probably my favourite big city. I would stay there again."

Find out more about Chesterfield District

Everything you need to know about Chesterfield District vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield District vacation rental for you. At Expedia, you can take your pick from private vacation 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 Chesterfield District vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield District vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield District. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield District vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield District vacation rentals we have selected for you start as low as CA $125 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield District rentals

At Expedia, we put the best Chesterfield District vacation 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 Chesterfield District 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 Chesterfield District vacation.

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

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Chesterfield District vacation rentals

1. The Old School House

2. Cedar Cottage

3. Overton

4. Cherry Tree Cottage

5. Gratton Grange Farm Holiday Cottage

6. No2

7. Rock Mill Retreat

8. Three Cranes Serviced Apartments

9. 2 Car Parking Spaces, Pet Friendly, Central Bakewell In The Peak District

10. Stone built self-catering lodge in stunning location

11. Kingfield Boutique Hotel

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

13. Rose Cottage - Cosy Cottage in Millers Dale

14. The Rumblings 1

15. Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom

16. No 11

17. Old Nags Head

18. Brewers Cottage - sleeps 2 guests in 1 bedroom

19. Sheffield Metropolitan by Belvilla - Standard Double Room

20. Spacious 5BR Sheffield Home | City Access & WiFi

Find vacation rentals that suit your style

Top Chesterfield District Hotel Reviews

voco Sheffield by IHG

Buxton Crescent

Courtyard By Marriott Sheffield

Leonardo Hotel Sheffield

ibis Budget Sheffield Centre St Marys Gate

Novotel Sheffield Centre

Radisson Blu Hotel, Sheffield

Old Hall Hotel

Eastwood Hall

Find out more about Chesterfield District