Pet-friendly vacation rentals in Chesterfield

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Chesterfield

  • Total vacation rentals

    Explore 50 vacation rentals in Chesterfield

  • Nightly prices starting at

    Chesterfield vacation rentals start at G$8,366 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chesterfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

  • 4.9 Average rating

    Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Chesterfield

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

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Top guest favorite
A traditional stone barn conversion is visible, showcasing a well-maintained exterior with multiple windows and doors. The surrounding gravel driveway leads to a serene countryside setting, highlighted by greenery in the background and a clear blue sky above.
Condo in Holymoorside
4.98 out of 5 average rating, 228 reviews

Dog Friendly, Cosy, Peaceful, Walks, Peak District

The Spinney is our super dog-friendly ground floor self-catering accommodation! We've designed it so that you & your dog have a great holiday! Part of a traditional stone barn conversion located in the Peak District & Derbyshire Dales, the Spinney offers space as well as the comfort of modern living. With cosy underfloor heating throughout, and everything you need for you and your furry friend, we are sure you will have a great time here! Peaceful setting, close to popular visitor attractions!

Top guest favorite
A well-maintained pathway leads to a beautifully designed cottage surrounded by lush greenery. The property features manicured hedges and trees, with a clear blue sky overhead, creating a welcoming entrance to the private garden area.
Guesthouse in Derbyshire
4.99 out of 5 average rating, 192 reviews

Springwood Cottage Private and Unique

Springwood Cottage is ideally situated in a beautiful location on the edge of Derbyshire is completely self contained with its own entrance and private garden area with parking outside. The Cottage is completely newly built in 2020 and designed to the highest standard. Well behaved Dogs welcome, we are happy to accommodate 2 dogs, please request if you have more than 2. A deluxe super kingsized bed (6 x6 foot) with the most up to date memory foam mattress and a comfortable sofa bed in the lounge

Top guest favorite
A cosy living room features comfortable seating on two plush sofas, arranged around a central ottoman. A stone fireplace with a woodburner creates a focal point. Exposed beams highlight the ceiling, while the space is adorned with floral cushions and a decorative area rug.
Cottage in Baslow
4.94 out of 5 average rating, 336 reviews

Characterful 2 bed cottage in excellent location

A charming cottage overlooking a babbling, nature-rich brook. Full of character, this peaceful cottage boasts a cosy living room complete with woodburner, underfloor heating and exposed beams, a fabulous kitchen and a stylish bathroom. The cottage is in a superb location with top-class restaurants, the magnificent Chatsworth Estate and truly stunning local walks right on the doorstep. Bikes can be stored in the rear yard making this cottage an ideal base for foodies, cyclists and walkers alike.

Top guest favorite
A spacious lawn leads to a charming stone cottage, surrounded by well-maintained greenery. The bright blue sky and scattered clouds enhance the inviting atmosphere, while the driveway provides access to the property and its scenic surroundings.
Cottage in Derbyshire
5 out of 5 average rating, 279 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

Top guest favorite
A stone exterior of the building is highlighted, featuring a prominent navy-blue door framed by two windows. Soft lighting enhances the entrance, surrounded by a neatly landscaped area with low shrubs and pavers leading to the door.
Cottage in Matlock
4.99 out of 5 average rating, 278 reviews

The Kennels

Kick off your walking boots, wash down your bike or just park up the car, this freshly converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

Top guest favorite
A spacious studio is seen, featuring a wooden double bed and a breakfast bar with stools. Comfy chairs are positioned near a large television. Soft carpeted flooring complements the pastel-colored walls, and kitchen appliances are visible in the background, providing functional living space.
Apartment in Chesterfield
4.96 out of 5 average rating, 293 reviews

Cosy studio apartment close to Peak District

Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

Guest favorite
A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.
Home in Chesterfield
4.96 out of 5 average rating, 347 reviews

The Long Hall 2 bed ground floor annexed apartment

Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

Top guest favorite
Barn in Holymoorside
4.99 out of 5 average rating, 188 reviews

Charming grade II listed cottage with hot tub

Chander Hill Cottage is a stylish 3-bedroom barn conversion nestled above the village of Holymoorside, on the edge of the Peak District. This cosy cottage is a perfect base for exploring the countryside, with numerous walks from the door and two pubs just a mile away in the village. Relax in our hot tub with stunning views or warm up by the wood burning stove after a winter walk. The enclosed cottage garden has a patio where you can enjoy a BBQ in the summer. Dogs welcome!

Top guest favorite
Guest suite in Ashover
4.98 out of 5 average rating, 385 reviews

Cosy self contained studio - Peak District

Set in the glorious Peak District in a rural and peaceful location is our lovely self contained studio. Glorious views and walks over rolling countryside. Close to Chatsworth House and Haddon Hall. With the popular wedding venue (Peak Edge Hotel ) within walking distance and the beautiful market towns of Bakewell, Matlock and Chesterfield (with its famous crooked spire) close by you can easily explore the Peak District from here. Perfect for the Chatsworth Christmas market.

Guest favorite
A wooden hot tub is positioned outdoors, surrounded by tranquil countryside. Rolling hills form a scenic backdrop, and a wooden ladder leads to the tub. A peaceful atmosphere is enhanced by the natural setting and distant trees.
Tent in Edale
4.87 out of 5 average rating, 574 reviews

Cozy Couples Glamping - Private Hot Tub

**Updated for 2026** Escapism at its finest. Find yourself rested and renewed at our idyllic glamping site nestled amongst the rolling hills of the Peak District. Updated and improved for Spring - Summer 2026! - We specialise in couples experiences; Birthdays, Anniversaries, Engagements, reach out to us to discuss how we can help make your occasion special. We guarantee that here, you can truly experience the meaning of a retreat.

Top guest favorite
The kitchen features a rustic design with shaker-style cabinetry and wooden countertops. A farmhouse sink is positioned under a window, complemented by modern appliances. A wooden dining table and chairs offer a cozy dining space, illuminated by warm lighting and natural materials.
Barn in Eyam
4.97 out of 5 average rating, 153 reviews

Jacobs Barn, Eyam

Jacob's Barn, entire home in the Village of Eyam, Peak District National Park UK Up to 4 guests, 2 bedrooms 2 beds, 1 bathroom There is going to be much to love about your stay at Jacob’s Barn! Nestled in the pretty historic village of Eyam, (The Plague village), it is perfectly positioned to make the most of the hilly green valleys of the surrounding Peak District National park.

Top guest favorite
A spacious interior features a warm wood-burning stove adjacent to a comfortable sleeping area. Two inviting armchairs are placed upon a soft area rug. Natural light streams in through the skylight and window, illuminating the simple, yet elegant decor.
Barn in Ashover
5 out of 5 average rating, 156 reviews

Beautiful barn conversion.

Reconnect with nature at this unforgettable escape on the edge of the Peak District. Beautifully finished barn conversion. King sized bed, tv with full Sky package. Log burner. Bathroom with freestanding bath and separate shower. Fully equipped kitchen. Outside seating/bbq area. Village and pubs within walking distance. Fantastic walking area. Stunning views. Plenty of parking.

Popular amenities for Chesterfield pet-friendly home rentals

When is the best time to visit Chesterfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$24,470 GYDG$24,261 GYDG$24,679 GYDG$23,215 GYDG$23,634 GYDG$24,470 GYDG$26,353 GYDG$27,398 GYDG$24,679 GYDG$24,889 GYDG$23,425 GYDG$24,679 GYD
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