Vacation rentals in Chesterfield

4.84 out of 5 average rating, 122 reviews

A stone cottage is framed by lush greenery and vibrant flowers. A small white bistro table with ornate chairs is positioned on a natural stone path, inviting leisurely outdoor moments. The building's rustic exterior and climbing plants enhance the charming countryside atmosphere.

Cottage in Youlgreave

Riverdale View - birds bees river & trees +garden

"Superb location, beautiful cottage" down the cobbled footpath towards the river. Private terrace & garden, heritage decor, hi speed Broadband. Soak in the roll top bath gazing at the fossil wall. Pull off your walking boots & rest on the church pew. Dim the lights, snuggle up with a glass of wine & cosy fire. Outdoor bistro table with nature all around. River 30 steps down for walks & swim! 3 pubs serve food & grocery shops nearby “undoubtedly the most lovely, wonderful place we have stayed at”

A peaceful scene depicts the still water reflecting the nearby stone buildings and lush greenery. Tall grasses line the banks, enhancing the natural tranquility of the environment. The stone pathway is visible, leading toward a residential area in the background.

4.94 out of 5 average rating, 365 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.

4.97 out of 5 average rating, 171 reviews

A wooden table with matching chairs is set on a gravel area, surrounded by greenery. The view showcases expansive fields under a partly cloudy sky, with blue hues dominating the landscape, creating a serene outdoor space for relaxation.

Home in Alton

Quiet cottage with beautiful surroundings

Welcome to Honeysuckle cottage located in Alton, Staffordshire. Surrounded by green countryside and picturesque walks, our cottage is in nice quiet part of the village and is the perfect rural escape. A short stroll away from the village shops and pubs and a 10 minute drive from the local ice rink, cinema and polar bear experience. With ample free off road parking the cottage is great for families couples or meeting up with friends for a get together. 2 double bedrooms and one single 2 lounges

A charming stone cottage is surrounded by lush greenery and manicured lawns, with neatly trimmed hedges framing the entrance. A gravel driveway leads to the front, complemented by mature trees and landscaped areas, providing a serene and inviting outdoor space.

5 out of 5 average rating, 211 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

4.9 out of 5 average rating, 121 reviews

A scenic landscape features rolling hills adorned with vibrant purple heather under a colorful sky at sunset. The backdrop showcases distant valleys, while large boulders in the foreground highlight the natural beauty of the area.

Townhouse in Derbyshire

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.

4.77 out of 5 average rating, 114 reviews

A patio area features a round wooden table surrounded by six folding chairs. A wooden fence encloses the space, with shrubbery and a large tree visible in the background. A relaxing atmosphere is suggested by the openness of the surroundings and the light blue sky.

Home in Alton

The Alders Cottage - Stunning views!

Beautiful stone built cottage in the heart of rural Staffordshire with stunning views of the rolling English countryside and just five minutes’ drive from Alton Towers! This stylishly renovated cottage in the lovely village of Alton is bright and airy with Wifi, TV, street parking and a sun trap patio garden. Sleeping six and with country walks, cycle trails and popular pubs nearby Felicity’s Cottage is the ideal cosy base for thrill-seekers and Peak District explorers. Easy self check in!

A small terrace area features a gravel surface surrounded by greenery. Two metal chairs and a round table are set against the backdrop of the cottage and rolling hills, providing a serene space for outdoor relaxation.

4.97 out of 5 average rating, 159 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.

A charming stone cottage exterior is adorned with lush climbing roses, showcasing vibrant red blooms. The front door is set within a natural stone archway, accompanied by blooming flowers in a welcoming garden. The windows feature a classic design with divided panes.

4.92 out of 5 average rating, 106 reviews

Stylish cottage inc. breakfast, sleeps 4

FREE Breakfast at the Old Original Bakewell pudding shop Welcome basket on arrival - Loaf of Bakewell Bakery bread, Pint of milk, bottle of Wine, bottle of local beer and the Old Original Bakewell Pudding Within a minuet’s walk of the shops, restaurants, pubs, cafes and the river Wye and large car parks *Walking, climbing and cycling on your door step *Outdoor area for al fresco dining *Cosy log burner in the living area *One parking space included *free WI-FI *Small dogs allowed

4.95 out of 5 average rating, 311 reviews

Cottage in Tideswell

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.

4.95 out of 5 average rating, 153 reviews

The entrance to No. 3 Club Cottages is highlighted by charming stone walls and a light blue front door. A small welcome light fixture is mounted beside the door, and the property number is displayed on a stone plaque next to it. Green foliage frames the entryway.

Cottage in Biggin

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.

4.8 out of 5 average rating, 217 reviews

Cottage in Carsington

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)

4.96 out of 5 average rating, 285 reviews

An outdoor patio area is featured, with a comfortable seating arrangement and a fire pit on a gravel surface. Lush green grass extends to the horizon, framed by scenic countryside views beneath a partly cloudy sky.

Hut in Derbyshire

Hillside Hut - with hot tub & private garden

Hillside Hut is our charming, newly developed, hut located in a secluded position on our smallholding in rural Derbyshire. With its own driveway and dedicated parking, it is situated in a very private spot enjoying stunning countryside views. Enjoy the most magnificent sunsets as you kick back and relax in this calm, stylish space. Bring your wellies! There are many countryside walks from the front door and fantastic dog-friendly village pubs within walking distance.

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What guests are saying

Clover Cottage - Hot tub, Sauna & Beautiful Views

4.82 out of 5 average rating, 303 reviews6 days ago

We had a fantastic time at Clover Cottage. The space was perfect for a short break, with the added luxury of a hot-tub. The host was responsive to our questions and provided a comprehensive ‘check-in’ walkthrough on arrival. Great location too for the peaks.

Farm stay in Derbyshire

What guests are saying

17th century cottage in Matlock

4.95 out of 5 average rating, 390 reviews2 weeks ago

We had a wonderful stay. It was a very comfortable and cosy cottage, both attractive and functional. We felt immediately relaxed there. Thank you to Jane - she went beyond expectations, providing items beyond what was listed in the description. Also, the decor made it a very homely and appealing place to be. There were DVDs, board games and books to use which we enjoyed. We would thoroughly recommend this place.

Cottage in Matlock

What guests are saying

Riverside Cottage Alstonefield Peak District

5 out of 5 average rating, 44 reviews4 days ago

Totally faultless. Everything you need and more. Every extra touch provided - including very generous welcome hamper and Easter tasteful decorations. Everything for a pet, or a picnic, staying in or going out. Modern technology including iMac, WiFi and sky. Nothing missing from the kitchen for any cook. Bedrooms and bathrooms (linen, towels, robes, toiletries) had the feel of a five star hotel. Charming hosts. I could go on. I had high expectations as is rated 10, but we were all astounded at how incredibly tasteful and well equipped it was, and to a high decorative standard. Thank you.

Cottage in Alstonefield

What guests are saying

Delightful 1 Bedroom Cottage

4.99 out of 5 average rating, 176 reviews5 days ago

The wife and I spent Easter weekend at Soozeys home and had to say it was a clean, immaculate home and as shown in the photos. It was lovely, warm and quiet too with a big bathroom which was nice along with clean towels etc.. very good. The bed was comfy with a thick quilt, which kept us toasty while we stayed. The house is on a narrow side street with only one way in and out. As mentioned in listing it's best to reverse into the street to get parked outside the house. We weren't able to park in the street for 2 out of the 3 nights we stayed as other cars were there but we're able to park on Market St at the end of the road for free, so no problem really... one thing to be aware of is that it can be a tight turning from Oddfellows St onto Market St due to the amount of parked cars. Definitely would stay again 😁

Home in Derbyshire

What guests are saying

The Perfect Romantic Bolthole

4.97 out of 5 average rating, 353 reviews5 days ago

We had an absolutely lovely week, so pretty and lots of lovely walks and things to do. Super clean and tidy, lovely host, and had everything we needed, even some snacks and basics! Instructions were clear and helpful. Local pub was great with tasty food too! Would highly recommend!

Home in Brassington

What guests are saying

Arraslea (2) Two Person Cabin with private Hot Tub

4.97 out of 5 average rating, 318 reviews1 day ago

We had. Wonderful stay in the cabin and used the hot tub everyday . The cabin was perfect for the two of us and the view from the cabin was amazing. We visited Chatsworth , Bakewell and Matlock . Guests get 10% off if you visit the bear inn , food was lovely nice choices would recommend . It’s a 4 min drive from cabin or 25 min walk .

Cabin in Derbyshire

What guests are saying

Cosy Grade ll listed cottage Central Peak District

5 out of 5 average rating, 240 reviews1 week ago

I have stayed in a quite a few Airbnbs and found Mereview cottage to be absolutely outstanding! The location is idyllic with amazing views of the mere and a local pub that provides great food. The cafe (a converted smithy) also deserves a shout out with top notch all day breakfasts!! Mereview cottage was beautiful and tastefully decorated with a lot of thoughtful additions including a selection of teas and a Bakewell pudding on arrival! I cannot wait to come back and spend more time in beautiful Derbyshire, especially from such a stunning base ! Thank you to such great hosts !

Cottage in Monyash

What guests are saying

Sweet & Dreamy Damson pod NEW - 3Trees Glamping

5 out of 5 average rating, 6 reviews6 days ago

Our stay in the Damson Pod with Sarah and family was perfect. The pod itself was lovely, beautifully clean and had all the amenities we needed. The view from the full glass front was spectacular and could be enjoyed while sitting in bed or on the outside seating areas. The land surrounding the pods was beautifully maintained and had space for sitting, BBQ's and a lovely dedicated space for the children to play with the provided toys. One evening we met Sarah in the adjoining field and had the opportunity to feed the Alpacas. We were kept well informed of the arrangements and details for arrival. We very much enjoyed our stay and have already recommended it to friends.

Cabin in Wirksworth

What guests are saying

Arraslea (1) Four Person Cabin with private HotTub

4.9 out of 5 average rating, 131 reviews1 week ago

Wonderfully peaceful surroundings and a great base to explore the local area for a few days. The cabin was just as described and our two boys loved waking up and just watching the animals (as did our dog). Would highly recommend if you’re looking for a relaxing (hot tub was again a big hit with the kids) break while there are also beautiful walks and things to do close by.

Cabin in Alderwasley

What guests are saying

Thors @ Hall Farm - Stunning views and playbarn

4.86 out of 5 average rating, 118 reviews2 months ago

Surprisingly easy to find, Emily's cottage is a lovely place with beautiful views. It was fully prepared for our arrival. We arrived very late due to delays but the contactless check in was smooth and the lovely hosts stayed in touch all the while. The property sleeps five but it felt cosy for our party of four (2 adults and 2 teenagers), but should be fine for a single family with little ones or couples. The location of the property is really good for walks and close to Thor's cave, but given the terrain the roads are narrow and you wouldn't want to be driving to and fro many times a day. This is true for most areas in the peak district. The was plenty of information available at be the property and the hosts were extremely responsive so guests won't be stuck for anything. All in all, it was a really nice stay!

Cottage in Derbyshire

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Popular amenities for Chesterfield vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Gym

BBQ grill

Stay near Chesterfield's top sights

Cineworld Cinema Chesterfield19 locals recommend

Linacre Reservoirs16 locals recommend

The Peacock At Barlow14 locals recommend

Chesterfield Market8 locals recommend

Nonnas Chesterfield7 locals recommend

The Tickled Trout7 locals recommend

Dog friendly vacation rentals in Chesterfield

4.98 out of 5 average rating, 107 reviews

A cozy lounge area features a pink armchair positioned next to a wood-burning stove, with a stack of logs visible below. A modern television is mounted above the fireplace, and natural light enters through two window panes with shutters. A lantern and small decorative elements complete the space.

Home in Tideswell

A chic retreat in the Peaks

4.8 out of 5 average rating, 207 reviews

An entrance pathway leads through a wooden exterior to a welcoming doorway. Large windows offer natural light, while a wrought iron gate introduces a secure outdoor area. The stone wall complements the rustic design of the lodge, enhancing the natural surroundings.

Cottage in Chelmorton

Cheedale Lodge

4.87 out of 5 average rating, 175 reviews

A scenic view captures rolling green fields dotted with sheep, extending towards a distant stone farm building surrounded by hills. The landscape is characterized by rustic stone walls and a serene, open sky, evoking a peaceful rural atmosphere.

Cottage in Buxton

Cosy Little Cottage in the Peak District

4.87 out of 5 average rating, 160 reviews

The exterior of a rustic stone cottage is presented, featuring two windows with white curtains and a green door that provides access inside. Flower pots with vibrant blooms are positioned in front of the cottage, complemented by a bright blue sky overhead.

Cottage in Castleton

Harry Eyre Cottage, Castleton, Peak District

4.95 out of 5 average rating, 198 reviews

A modern kitchen is illuminated by pendant lights, featuring wooden cabinetry and slate flooring. A dining table is set with plates and glassware, ready for a meal. Large windows allow for natural light, showcasing views of the garden and surrounding landscape.

Home in Harpur Hill

Dog & Cycle friendly house with enclosed garden

5 out of 5 average rating, 102 reviews

An outdoor patio area is visible, featuring a rustic wooden table surrounded by scattered chairs. Potted flowers add vibrant color to the space, while nearby stone walls complement the natural setting. Beyond the patio, greenery and distant hills enhance the tranquil atmosphere.

Barn in Castleton

Dog Friendly Speedwell Stable at Speedwell House

4.99 out of 5 average rating, 107 reviews

A tranquil bedroom is presented with two spacious beds adorned with soft white linens and elegant gray throw pillows. Fluffy towels are neatly rolled at the foot of each bed, while natural light illuminates the room, highlighting minimalist decor and a stylish vanity area.

Cottage in Tideswell

The Old Toffee Shop

4.98 out of 5 average rating, 133 reviews

A serene pond is surrounded by lush green foliage and trees. Water lilies float on the surface, reflecting the natural beauty of the garden. A wooden structure can be seen in the background, blending with the landscape.

Condo in Derbyshire

Spacious, dog friendly, one level accommodation.

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Other great vacation rentals in Chesterfield

4.99 out of 5 average rating, 108 reviews

Rowan Tree Cottage

4.96 out of 5 average rating, 168 reviews

Farm stay in Derbyshire

Luxury newly converted oak cottage

5 out of 5 average rating, 210 reviews

Cottage in Bakewell

Rocking Stone Cottage - Idyllic Rural Retreat

4.99 out of 5 average rating, 258 reviews

A private garden area is surrounded by tall fences and lush greenery. A gravel pathway leads toward the cabin, which features large windows. A seating area is visible, offering a serene view of the landscaped yard, with gentle sunlight filtering through the trees.

Guesthouse in Derbyshire

The cabin @ white cottage

Cottage in Earl Sterndale

An inviting entrance to Critchlow Cottage is framed by lush green ivy climbing the stone exterior. A wrought iron gate leads to a pathway surrounded by well-maintained hedges and grass, providing access to the front door.

5 out of 5 average rating, 9 reviews

Dog-friendly Critchlow Cottage in Earl Sterndale

4.99 out of 5 average rating, 83 reviews

A round glass table is set on a wooden deck, surrounded by a dark wicker seating arrangement. The expansive views of rolling hills and greenery in the distance are visible beyond the railing, providing a serene backdrop.

Farm stay in Cauldon

Escape to the country

4.96 out of 5 average rating, 211 reviews

Home in Ashbourne

Gag Barn Nr Thorpe (Peak District/Dovedale)