Pet-friendly vacation rentals in Cheltenham

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Top-rated pet-friendly home rentals in Cheltenham

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Guest favorite

Home in Gloucestershire

4.87 out of 5 average rating, 107 reviews

Unique luxury boutique Cheltenham town centre

Experience refined living at Milton House, a chic, 2-bedroom, 2-bath oasis in Lansdown Walk, Cheltenham. Enjoy an open-concept space with floor-to-ceiling doors leading to a stunning terrace, designed by top London and Cotswolds designers. The loft is furnished with high-quality decor, Egyptian cotton linens, and luxurious White Company toiletries. Steps away from upscale shopping, nightlife, and renowned festivals, Milton House also provides easy access to the picturesque Cotswolds countryside!

Apr 10 – 17

R6,855 ZAR per night

Guest favorite

Home in Boddington

4.98 out of 5 average rating, 100 reviews

Stunning Victorian Mill, 3 BDR

Oriri presents Boddington Mill, a stunning countryside retreat steeped in history and rural charm. Multiple levels intersect the original mill parts for a generous and sociable living space. A south-facing garden includes alfresco dining, wood-fired hot tub, and large lawn, home to fruit-bearing trees and wildlife. Bedrooms feature luxury bedding; vaulted, oak-beamed ceilings; and period windows. Guests will enjoy fine comforts, modern media, and a kitchen fit for the highest culinary ambitions.

Mar 29 – Apr 5

R12,850 ZAR per night

Guest favorite

Chalet in Cheltenham

4.95 out of 5 average rating, 193 reviews

Fantastic isolation Cotswolds hideaway Cleeve Hill

Self-contained apartment built-in full kitchen, Nespresso machine, Oven, Hob, Fridge, Freezer, Microwave Dishwasher, Washer-dryer etc. Luxury Travertine walk-in shower with overhead rain & hand-held sprays. It is 2.5 miles to the town centre and 1 mile to race course. Suits couples, business travellers, and furry friends (dogs by prior notice and fee). Bose bluetooth speaker, super fast internet and large Sony smart TV with chrome cast. Very quiet and remote in gated grounds of up to an acre.

Nov 9 – 16

R2,514 ZAR per night

Guest favorite

Apartment in Gloucestershire

4.93 out of 5 average rating, 161 reviews

spacious, stylish, central, child friendly

Fully self contained flat in central Cheltenham ideal for family’s. This freshly painted, furnished apartment is in a great location to walk into Cheltenham. John Lewis on the High Street is just a 7 min walk. Cheltenham Racecourse is 10-15 min walk. Surrounded by parks and beautiful town of Cheltenham with all its festivals and night life. The Cotswolds are just a short drive away. Two luxurious large bedrooms. Master with double bed. Second bedroom two singles beds and a fun bunk bed room.

Dec 9 – 16

R2,514 ZAR per night

Guest favorite

Condo in Gloucestershire

4.9 out of 5 average rating, 175 reviews

Period 1 bed apartment in the heart of Cheltenham

Beautiful period 1st floor one bedroom apartment has just been fully refurbished right in the middle of Cheltenham town center. Ideal for 3/4 people the apartment comprises of open plan large lounge/kitchen/diner, complete with a sofa bed, new shower room and a double bedroom. Brand new kitchen is fully equipped with integrated appliances like an induction hob, fridge/freezer, oven, dishwasher and microwave. Nespresso coffee machine. The apartment has everything you need for a relaxing stay.

Jul 25 – Aug 1

R3,351 ZAR per night

Guest favorite

Tiny home in Witcombe

4.88 out of 5 average rating, 481 reviews

Little Knapp on the Cotswold Way

Snug space ideal for relaxing getaways. Set in area of outstanding natural beauty. Perfect for couples keen to explore the Cotswolds with direct access to the Cotswold way. It's a quirky small space. Intended as a great escape, there is WiFi but no TV. Dogs: As space limited 1 w-behaved dog welcome (+ £10). Sofabed: Please request bedding (+£10 charge) or bring own for free. NB Bathroom space is limited, stairs may be tricky for less mobile, roof terrace is private but overlooked by our house.

Oct 15 – 22

R2,063 ZAR per night

Guest favorite

Condo in Gloucestershire

4.87 out of 5 average rating, 163 reviews

Intriguing Apartment in Regency Villa

An intriguing designed and modern 91 square metre apartment in a Regency Villa. With designer furnishings, and stunning limestone flooring. The apartment has been renovated to a pristine standard with feature lighting. Located on the prestigious Montpellier Terrace, the apartment looks onto the famous Cheltenham festivals in Montpellier gardens, and is within a small walking distance to all the Restaurants and Bars that the central and stylish Montpellier district of Cheltenham has to offer.

Oct 17 – 24

R3,060 ZAR per night

Guest favorite

Guest suite in Sheepscombe

5.0 out of 5 average rating, 211 reviews

Idyllic rural location in Sheepscombe village

A self contained annexe on a working small holding which has recently been refurbished to a high standard. It is overlooking the unique village of Sheepscombe with fantastic panoramic views over the village and surrounding National Trust beechwoods. This rural retreat is a walkers paradise, dog friendly with close access into the woods behind and near to the Laurie Lee way in the Slad Valley. Stroud, Cheltenham, Cirencester and Gloucester are a short drive away. An idyllic quiet get away.

Aug 16 – 23

R2,705 ZAR per night

Guest favorite

Cottage in Bank Farm Barns

4.99 out of 5 average rating, 403 reviews

Idyllic Dog Friendly Barn , Summerhouse / Paddock

“Hare Barn” is self contained original barn conversion We offer guests on B & B basis the perfect place to relax and unwind. Many character features including romantic bedroom, private patio and access to my paddock offering spectacular views towards Bredon Hill and countryside. Use of The Stables Summerhouse with sheltered seating., BBQ, Firepit & Fridge. Extensive network of footpaths perfect for dog lovers and ramblers, leading direct from barn. Up to 3 dogs stay free

Feb 17 – 24

R2,866 ZAR per night

Guest favorite

Guesthouse in Worcestershire

4.95 out of 5 average rating, 183 reviews

Cleeve Cottage (The Studio)

A small detached studio/annex, in the picturesque village of Bushley, ideal location for anyone looking to have a short break in the countryside just 1.5 miles from the old market town of Tewkesbury and only 20 minutes from Cheltenham so perfect for a weekend at the races. Plenty of stunning rural locations to be explored nearby, with easy access to the beautiful Malvern hills, fantastic for cycling and hiking

Sep 25 – Oct 2

R1,979 ZAR per night

Guest favorite

Cottage in Cheltenham

4.94 out of 5 average rating, 111 reviews

The Stables - Luxury Central Cheltenham Bolthole

Gorgeous converted stables located in the heart of Cheltenham originally belonging to a Georgian Villa, this is the ideal place to stay for a long weekend or mid week break in the Cotswolds. Perfectly located within walking distance of the bars and restaurants of the Suffolk's and Montpellier, and all that Cheltenham has to offer, be that one of the many the festivals or of course the races .

Nov 27 – Dec 4

R3,705 ZAR per night

Guest favorite

Chalet in Berrow, Worcestershire

4.98 out of 5 average rating, 184 reviews

The stables ,rural location and dog friendly

The Stables is a self contained single storey property with a private garden on our smallholding, dog friendly but please read house rules/ additional rules regarding pets. we are ideally situated for weddings at Birtsmorton court (less than 5 minutes away) and Eastnor Castle ( 10 minutes away) for exploring Malvern Hills Cotswolds Forest of dean The wye valley and Herefordshire Cheltenham

Nov 29 – Dec 6

R2,842 ZAR per night