Family-friendly vacation rentals in Chesterfield

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Top-rated family-friendly rentals in Chesterfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Tibshelf

4.97 out of 5 average rating, 286 reviews

Hunters Cottage. Wheatsheaf Mews

Our cottage is situated directly on the Five Pits Trail, which provides miles of trails for walkers, bike and horse riders, there are also fishing ponds 500m along the trail. It's a beautiful character cottage newly renovated to a high standard. It is ideally situated, with Hardwick Hall 5 minutes drive away and the Peak District on our doorstep. Matlock, Crich Tramway Village, Chatsworth House and Haddon Hall within half an hour. We also have a hottub for you to relax in at the end of your day.

Sep. 3 – 10

$273 CAD per night

Guest favourite

Barn in Youlgreave

4.98 out of 5 average rating, 455 reviews

Immaculate Studio - Heart of the Peak District.

New Build in the heart of the Peak District - Youlgrave, nr Bakewell. Plenty of private parking. (No pets - sorry). 200 yards from the Limestone Way. A walk in any direction is beautiful. 3 pubs within 10 mins walk all serve food. Peak feast bakery for cakes, bread, coffee, homity pies and delicious vegetarian food. A well-stocked village shop with cafe for all other needs, a licensed post office, a park and playing fields are all 5 mins walk away. Fantastic views from your 'studio' bedroom.

Apr. 22 – 29

$131 CAD per night

Guest favourite

Cottage in Derbyshire

4.99 out of 5 average rating, 149 reviews

2 En-suite rural luxury cottage Ashover Derbyshire

Rural luxury 2 bedroomed en-suite cottage with kingsize bed & twin or superking. Both bedrooms have en-suite facilities one with walk in rain shower and twin with shower over bath. Ideally situated for the Peak District, Bakewell, & Chatsworth. Underfloor heating throughout and looks out onto its own woodland with picnic bench plus 2 more seating areas ideal for 2 couples. BBQ & table & chairs with cushions. Perfect for chilling out with views and walks from the doorstep. Pub 10 minute walk.

Feb. 14 – 21

$302 CAD per night

Guest favourite

Apartment in Sheffield

4.98 out of 5 average rating, 444 reviews

The Hollies - Luxury self contained apartment

This garden flat with separate access is located in the heart of Sheffield's academic and healthcare hubs. Nestled between Broomhill, Ecclesall road and 2 miles away from the city centre. Close to Botanical Gardens, Endcliffe park and a short walk to a variety of restaurants and pubs. With an en-suite bathroom, well equipped kitchen and small private patio this apartment is perfect for everything Sheffield has to offer! We have 2 friendly dogs and a cat. We also have free overnight parking.

Sep. 4 – 11

$149 CAD per night

Guest favourite

Home in Derbyshire

4.92 out of 5 average rating, 212 reviews

Charming, converted Grade II listed Chapel (1838)

My place is surrounded by breathtaking scenery. Family activities are close at hand. You’ll love my place because of its homely feel - lots of guests have commented that they feel at home in Chapel House, its fabulous aspect and its magical character. My place is perfect for couples and families. Its open-plan design cultivates holiday togetherness. Relaxation comes easily here. My village has two lovely pubs. The Gate was awarded 'Most Unspoilt Pub in England 2017' by The Good Pub Guide.

Jun. 4 – 11

$232 CAD per night

Guest favourite

Home in Eyam

4.97 out of 5 average rating, 289 reviews

Beautiful home with Stunning views and log fire

Come and escape to this relaxing slice of paradise. Surrounded by lush green countryside and stunning scenery, Longcroft View is the perfect getaway to put your feet up and relax or explore all the beauty the Peak District has to offer. With two large bedrooms both (en-suite) and a fully stocked country style kitchen it's the perfect choice for family or friends to stay. The incredibly cosy lounge houses a 3 piece suite, log burning fire, games for all ages and a 55" 4K smart TV.

Feb. 15 – 22

$172 CAD per night

Guest favourite

Apartment in Derbyshire

4.98 out of 5 average rating, 388 reviews

1 Dalebrook View, Stoney Middleton

A spacious modern apartment in the heart of the Peak District surrounded by beautiful countryside. Great for families and for groups of friends that might want a walking holiday. Two of the bedrooms can be made up as twin beds or superkingsize. The third bedroom has a double bed. There is also a cot and high chair in the apartment. Stoney Middleton has a friendly pub, village chip shop and a curry cottage with a cave! Chatsworth, Bakewell, Eyam and Grindleford are all nearby.

Mar. 8 – 15

$179 CAD per night

Guest favourite

Home in Baslow

4.93 out of 5 average rating, 332 reviews

Comfortable cottage on the Chatsworth Estate

Yeldwood Farm Cottage is a beautiful barn conversion on our farm, just outside Baslow. The self-catering cottage sleeps 2 guests, in a Super-King size (or Twin) master bedroom. The cottage comprises a fully equipped kitchen, dining room, sitting room and bathroom with a large bath and shower. We are ideally situated on the Chatsworth Estate within the Peak District, close to Chatsworth House itself, Haddon Hall, Bakewell, Eyam, Matlock, Castleton, Buxton and Sheffield.

Sep. 12 – 19

$172 CAD per night

Guest favourite

Home in Sheffield

4.92 out of 5 average rating, 473 reviews

Old Coach House. 5*. Parking. UltraFast Wi-Fi

“Loved staying here”. It’s your own little house! Perfectly located in leafy Nether Edge village, 10 minutes from city centre and Peak District. Near to local shops, pubs, cafés and restaurants. Everything you need for the perfect stay: Private off-street parking: Yes. Big comfortable beds: Yes. Powerful shower: Yes. Washing machine: Yes. New kitchen: Yes. Spotlessly clean: Yes. Ultra-fast 1GB fibre optic broadband/Wi-Fi: Yes. Charm, character, history? Yes. Yes. Yes!

Nov. 23 – 30

$178 CAD per night

Guest favourite

Cottage in Derbyshire

4.96 out of 5 average rating, 170 reviews

The Hayloft - in the Peak District near Ashbourne.

The Hayloft is a spacious studio apartment surrounded by beautiful Derbyshire scenery in the tranquil village of Bradley near Ashbourne. There could hardly be a more peaceful setting, surrounded by fields and with Mill Dam Lake on the opposite side of the road. The surrounding area is ideal for walking, cycling and outdoor pursuits with the Tissington Trail, Dove Dale & major attractions like Chatsworth House & Alton Towers within easy reach.

Jan. 16 – 23

$184 CAD per night

Guest favourite

Guesthouse in Tansley

4.97 out of 5 average rating, 439 reviews

Beautiful Self Contained Cottage in Derbyshire

Stunning Derbyshire Village self contained Cottage set within 1/2 acre of gardens in the picturesque village of Tansley. 1 mile from Matlock, 9 miles from Bakewell and Chatsworth. large double bedroom, open plan kitchen, dining and living area and separate bathroom with electric shower. Egyptian Cotton Bedlinen M&S Luxury Towels Self serve Continental breakfast included in price. Milk orange bread, fruit, cereals etc

Jul. 5 – 12

$160 CAD per night

Guest favourite

Cottage in Barlow

4.85 out of 5 average rating, 217 reviews

Old Barn Conversion close to the Peak District

This beautiful detached barn conversion has been charmingly renovated, retaining and working with many original features where possible. Tastefully furnished to a very good standard throughout, the open-plan living space has a small/compact kitchen area with a combi/microwave oven and hob. Its stunning beamed vaulted ceiling creates a warm and cosy social environment.

Oct. 23 – 30

$174 CAD per night