Chesterfield cottages
We found 440 cottages — enter your dates for availability
Explore Chesterfield cottage rentals
Countryside cottage on the edge of the Peak District
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
CUCKOO NEST, with a garden in Ashover
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
HIGHVIEW STABLES, pet friendly, with hot tub in Chesterfield
Sleeps 4 · 1 bedroom · 1 bathroom
Charming Croft Cottage on the doorstep of the Peak District near Barlow
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
THE RUMBLINGS 1, pet friendly, character holiday cottage in Barlow
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
THE TACK ROOM COTTAGE, pet friendly, with a garden in Ashover
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated cottage rentals - Chesterfield
Cosy cottage
1010 out of 10
Exceptionalexceptional
200 reviews(200 reviews)
Gorgeous cottage, clean, comfortable and quiet. Lots of places around to visit and lots of lovely restaurants. Bakewell is a lovely town, lots of shops and eateries. Highly recommend Chatsworth house, the gardens are amazing. Had gorgeous meals at the Derbyshire arms, just a short walk from cottage and the Chakra lounge, a beautiful vegan/vegetarian Indian with gluten free options in Bakewell.
Samantha G.
Stayed Jul 2025
Good Walking Base
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
We had a lovely 9 night stay in Kingfisher Cottage, it is ideally situated for walking with lots of routes from outside the front door. the cottage is comfortable and extremely well equipped with plenty of crockery, utensils etc enabling you to prepare meals, couple of good pubs in the village which serve meals. We loved the area and are planning on returning in the future.
Elizabeth L.
Stayed May 2025
Brilliant weekend
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Cottage lovely, very clean it had everything we needed.the bottle of wine was appreciated also the doggy towels,loved matlock,recommend the red lion for the carvery will definitely book again
Ruth L.
Stayed Apr 2025
Relaxing cosy cottage
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
A lovely cosy cottage in a beautiful rural area. The cottage is very well equipped and comfortable. The milk, biscuits and wine on arrival were a very welcome tou.ch
Karen D.
Stayed Feb 2025
Short break
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The property is ideal for a couple or small family group. The property is in one of the prime locations in Sheffield and as such is ideally located for any visit to the city or surrounding areas.
Gary M.
Stayed Nov 2024
Lovely stay
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Lovely cottage, great area, we really enjoyed a few days there.
Fiona J.
Stayed Oct 2024
Clara cottage
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Overall excellent experience, property well presented, clean & comfortable. Welcoming pack much appreciated & unexpected. Highly recommend though quite isolated.
William H.
Stayed Aug 2024
Lovely stone cottage
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Beautiful location and charming cottage.
John M.
Stayed Jun 2024
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Frequently asked questions
Are there any cottage rentals in Chesterfield?
Check out our 440 cottage rentals and start making plans for your trip to Chesterfield. Whether you'd like to be in Spital, Hasland, Wingerworth or another well-known neighbourhood, Vrbo's charming and cosy cottages offer more room to move compared to a hotel.
How much does it cost to stay in a cottage rental in Chesterfield?
Prices vary according to length of stay, season and property location, so enter your trip details to browse what's available. Whatever your plans or budget, Vrbo has cottage rentals in Chesterfield suited to guests of every type.
When is the best time to rent a cottage in Chesterfield?
It all comes down to your budget, your ideal weather and if you prefer the liveliness of the busy season or a more relaxing atmosphere. Located in Derbyshire, February attracts the most visitors to Chesterfield, when temperatures average between 1ºC (34ºF) and 6ºC (43ºF). Browse the availability of Vrbo's cottage rentals year-round and then pick your favourite.
Where can I rent a Chesterfield holiday cottage with great views?
Let your stresses drift away as you kick back and gaze at the views of historic areas from your inviting cottage rental in Chesterfield. Use our filters to search for cottages with outdoor areas, such as a deck or patio, so you can appreciate your surroundings even more.
Does Chesterfield have any lakeside cottages?
For a welcome change of scenery, you can't top our lakeside cottage rentals. Try our "Location" filter and then check the box marked "Lake" to see if you can find any cosy cottages that'll put you close to the water in Chesterfield. Spend your days chasing adventures or just enjoy seeing gorgeous sunrises and sunsets shimmering across the lake.
What are the top things to do in Chesterfield?
Ponds Forge International Sports Centre, Peace Gardens and Millennium Gallery are terrific attractions that'll keep the whole family occupied in Chesterfield. There's nothing like travel to bring everyone together, so browse our cottage rentals in this vibrant destination.
Why should I book my holiday cottage with Vrbo?
With Vrbo you'll never have to share your cottage rental with others, whether you're searching for a rustic stay in the countryside or an upmarket pad by the beach. Another awesome reason to book with us? You can filter your search by amenities, your budget and more to find a cottage rental that matches your needs and style. Also, our One Key™ rewards programme lets you earn and redeem OneKeyCash™* on eligible bookings made through Vrbo. Plus, our flexible cancellation policies and first-rate customer support also ensure a stress-free trip. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.