
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$8,383 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.

Chatsworth Cottage
Situated on the edge of the Peak District Park, this is the ideal base for exploring Derbyshire. The Cottage is situated on Chatsworth Road just 10 minutes drive from the ‘Palace of the Peak District’. A short journey and you will discover other wonders of the Peak at places like Matlock, Bakewell, Castleton and Buxton. The historic market town of Chesterfield and the famous Crooked Spire is just a 20 minute walk down the Brampton Mile where you will find some great places to shop, eat & drink.

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

Gorgeous romantic cosy cottage retreat with views
Welcome to Lancaster Cottage, Winster - the perfect luxury escape for couples in the Peak District. ~ Ideal cosy hideaway for a romantic escape for 2 ~ Secluded, off-road & immersed in nature with secret garden & log cabin ~Fabulous walks from the doorstep ~Lovely pubs within a few minutes walk ~Oozes character - built in 1701 & Grade II Listed ~ Cosy woodburner fireplace & beams ~Huge sink-in settee & a dreamy, romantic bedroom with king-sized comfy bed with stunning views ~Dog-friendly

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!

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.

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

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.

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.

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

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!

The Little Lodge
Kick back and relax in this calm, stylish space. The Little Lodge is a brand new renovated annex attached to a charming Victorian Lodge from the 1800s. Situated in a picturesque and peaceful conservation area on a private road in the leafy suburb of Ranmoor Sheffield. The Little Lodge is only 15minutes away from Sheffield's main train station and sits of the foothills of South Yorkshire's famous Peak District. Ideal for a city break or a Rambler's retreat.

Stretton Hall Farm - The Annex
Our holiday cottages & glamping pods are located on our 100 acre farm on the edge of the Peak District. The Annex is a modern barn conversion with a luxurious interior, designed to make it feel like a home away from home. Secluded down a 1/4 mile private driveway in a courtyard with the other cottages, the Annex has a quiet feel to it where you can truly relax. We are contractor friendly, please message us for work stays that are Monday to Friday.
Popular amenities for Chesterfield pet-friendly home rentals
Pet-friendly house rentals

Country Cottage with great outside space & views

Chert Cottage, Great Longstone, Bakewell Peak Dist

Derbyshire Gem, Peak District

Bridgefoot Cottage - Wild Swimming & Hot Tub

Hugo’s Luxury Barn

Willow Cottage Newly renovated quaint cottage

Pear Tree Lodge with private HOT TUB and garden

Sleeps 6 | Views of Curbar Edge, near Chatsworth
Pet-friendly home rentals with a pool

Boutique Retreat, Summer Pool, Peak District

Luxury Shepherd's Retreat with Hot Tub

Romantic Peak District Spa Cottage •Hot Tub & Pool

Dog Friendly Retreat

Family Home Getaway - Hot Tub, Sauna & Swim Spa

Spacious Dog Friendly Cottage by Carsington Water

Loki’s Lodge@ Ashbourne Heights holiday park

The Tissington Retreat, Ashbourne Heights
Private, pet-friendly home rentals

Cozy Couples Glamping - Private Hot Tub

Jacobs Barn, Eyam

2 En-suite rural luxury cottage Ashover Derbyshire

The Willows Hut - with hot tub - Hillside Huts

20 Lacemarket Panorama

Exclusive & Beautiful Modern Studio Flat

Cosy cottage with private garden

Badgers Bottom - Luxury Lodge at Mill Barn
When is the best time to visit Chesterfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$24,519 GYD | G$24,310 GYD | G$24,729 GYD | G$27,244 GYD | G$27,453 GYD | G$29,130 GYD | G$26,406 GYD | G$27,453 GYD | G$24,729 GYD | G$24,939 GYD | G$23,472 GYD | G$24,729 GYD |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
Destinations to explore
- Peak District National Park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- Heaton Park
- Donington Park Circuit
- Didsbury Village
- Lincoln Castle
- AO Arena
- Harewood House
- Tatton Park
- Bowlers Exhibition Centre
- Yorkshire Wildlife Park
- Bramham Park
- University of Manchester
- Manchester Central Convention Complex
- University of Leeds
- Temple Newsam Park
- Mam Tor
- Belvoir Castle
- Royal Armouries Museum
- The Piece Hall
- Motorpoint Arena Nottingham
- Manchester Central Library





