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Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Barn in Ford, Leek

4.94 out of 5 average rating, 175 reviews

5* Stunning Secluded Luxurious Converted Barn

5* TRIP ADVISOR REVIEWS-STUNNING SECLUDED RURAL LOCATION-GROUND FLOOR BEDROOM-LOG BURNING STOVE-NO CLEANING FEES You will find it hard to find anywhere else as peaceful & secluded as Ford Wetley Cottage in the Peak District, a beautifully luxurious appointed converted dairy. This unique space is secluded & surrounded by fields, trees, streams, waterfalls, woodland. Peaceful & relaxing, log burning stove, outdoor BBQ & river view decking and heated cabin. 2 acre field for dogs to explore. EV

Cottage in Derbyshire

4.94 out of 5 average rating, 342 reviews

Millstream Cottage

A Charming Grade 2 listed stone built terraced cottage with an allocated parking space outside the property, conveniently located in the picturesque market town of Bakewell. Very quiet but ideally positioned to explore the beautiful Peak District. There is a bus stop nearby where you can access transport to Manchester and Sheffield. Ideal for families or couples. Highchair and travel cot available on request. A welcome pack will be provided on your arrival to get your stay of to a great start.

Cottage in Derbyshire

5 out of 5 average rating, 163 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

Townhouse in Derbyshire

4.91 out of 5 average rating, 106 reviews

Period town house, right in the Heart Of Bakewell

Fabulous loft style living right in the heart of beautiful Bakewell Shops, pubs, restaurants, River and amazing walks on your doorstep. Ideal to explore the stunning dales. Parking permit supplied for 1 vehicle. Sleeps 8 guests in 2 bedrooms & can sleep up to 12 with the use of sofa beds in the lounge area (£25 pppn on request) All in a modern and bright setting. Fully fitted and well equipped kitchen. Fast wi-fi Adaptable sleeping arrangements, to accommodate larger groups and families.

Cottage in Derbyshire

4.98 out of 5 average rating, 129 reviews

Swiss Cottage, a heritage cottage, stunning views

Overlooking the beautiful tree-lined Derwent valley, the South facing Swiss Cottage is uniquely situated to offer panoramic views of the entire gorge and the picture perfect village of Matlock Bath, complete with an array of pretty lights, below. It provides the seclusion of a mountain retreat and access to all the village has to offer by way of a range of eateries from vegan to seafood, excellent pubs and entertainment for children from the Heights of Abraham to rowing on the river.

Cottage in Tideswell

4.95 out of 5 average rating, 300 reviews

Lovely Lavender Cottage Tideswell, Buxton

A cosy cottage in a thriving village. Pretty walled garden with garden furniture. Well equipped, with quality linen, towels. Bathroom with separate bath and great power shower. Bedroom one has a double bed and bedroom two has two singles which can be zipped together to make a king size. Great Wi-Fi signal. Family friendly, cot and high chair available. Sorry no pets. Two minute walk into the village situated away from the main road on the hillside. Self check in with key box.

Home in Derbyshire

4.84 out of 5 average rating, 261 reviews

Sunnyside Cottage, in the heart of Buxton

Situated in the heart of Buxton this cosy cottage is perfect for couples, friends and small families wanting to get away & unwind. Featuring 2 bedrooms, one king size, reclining sofas, gas logburner, Netflix, super fibre WiFi, this cottage offers an ideal blend of character & comfort! A short walk takes you to independent retailers, cafes and restaurants that fill quirky period buildings, Buxton Opera House, the tranquil Pavilion Gardens, and the magnificent Devonshire Dome.

Cottage in Litton

4.88 out of 5 average rating, 102 reviews

Peaceful cottage Peak District, nr Bakewell

Beautiful, peaceful cottage, ideal as a relaxing couples getaway in the heart of The Peak District close to Chatsworth House, Tideswell (Cathedral of the Peaks) Bakewell. Buxton. Fabulous walking from your doorstep. Wonderful pubs in the area. Private parking, private garden with a garden room. Stunning kitchen. Wood burning stove. Some wood supplied. Bathroom with freestanding bath, separate shower King size bed. Plus a double bedroom Perfect for a week of relaxation !

Cottage in Biggin

4.95 out of 5 average rating, 124 reviews

Cosy Traditional Peak District Cottage

A traditional Cottage in the idyllic village of Biggin in the beautiful Peak District. No3 Club Cottages is within walking distance of a popular village pub, Biggin Hall, and children’s play area. With plenty of footpaths, cycle trails and bridleways within walking distance, including the famous Tissington Trail. The Cottage has great views of the countryside, an enclosed garden/courtyard front & rear with seating areas, it also has a log burner for those colder evenings.

Cottage in Carsington

4.79 out of 5 average rating, 198 reviews

Luxury SC Cottage Lake views 6-8 Guests

FULLY REFURBISHED -Fabulous Lakeside cottage with unrivalled views over Carsington Water. The property is South facing, set in over an acre of garden. Beautiful walks, cycling, water & outdoor activities on your doorstep. Fantastic village gastro pub - The Miners Arms (2 min walk) central to over 100 attractions. A Hot tub can be hired in ready for use on arrival (extra charge) Please ask for details. Weekend breaks (Friday-Monday) or Midweek breaks (Monday - Friday)

Cottage in Matlock

4.95 out of 5 average rating, 365 reviews

17th century cottage in Matlock

A very old stone cottage but newly renovated inside. The cottage was my home, my children were all brought up there. I now live in a barn at the top of the driveway which we tried to build in as energy saving way as we could. During the cottage renovation we have tried to make the space as 'green' as possible.

Cottage in Youlgreave

4.97 out of 5 average rating, 136 reviews

Peak District village cottage with stunning views

An 18th century cottage recently renovated to become the perfect space to relax and enjoy the Peak District. 🛏 Sleeps 4 (2 kings or 1 king and 2 singles) 🛁 2 bathrooms 🐕 Dog friendly 🌳 Enclosed garden with stunning views 📍 Ideal Peak District location 🚶🏼 Walking distance to various pubs & shops

Vacation rentals for every style

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Popular amenities for Chesterfield vacation rentals

Free parking on premises

Air conditioning

Stay near Chesterfield's top sights

Morrisons5 locals recommend

The Market Pub4 locals recommend

Chesterfield Parish Church16 locals recommend

Queens Park5 locals recommend

Cineworld Cinema Chesterfield19 locals recommend

Chesterfield Market8 locals recommend

Other great vacation rentals in Chesterfield

Farm stay in Staffordshire

4.92 out of 5 average rating, 170 reviews

Hot Tub, Swimming Pool & Hay Loft in Peak District

Farm stay in Derbyshire

4.95 out of 5 average rating, 146 reviews

Luxury newly converted oak cottage

Home in Woolley Moor

4.98 out of 5 average rating, 108 reviews

Oldfield House Woolley Moor, Ashover, Derbyshire

Home in Ashbourne

4.96 out of 5 average rating, 197 reviews

Gag Barn Nr Thorpe (Peak District/Dovedale)

Cottage in Denstone

4.92 out of 5 average rating, 231 reviews

Peacock Cottage, only 3 miles from Alton Towers

Farm stay in Sheffield

4.9 out of 5 average rating, 865 reviews

The Cart Shed at Moorwood

Home in Derbyshire

4.88 out of 5 average rating, 129 reviews

Cheerful 2-bedroom home with free offroad parking

Cottage in Buxton

4.98 out of 5 average rating, 137 reviews

The Wriggly Tin, Millers Dale

Quick stats about vacation rentals in Chesterfield

Total rentals
100 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
5.6K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 50 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Apartment Rentals in Chesterfield?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Chesterfield have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chesterfield?
Experience the best of Chesterfield with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesterfield have wifi?
Absolutely! We offer over 50 house rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Chesterfield?
Make yourself at home in Chesterfield by choosing from our most frequently booked neighborhoods. We have over 180 vacation rentals in Chesterfield, and over 180 vacation rentals in Brimington CP.

Destinations to explore