Vacation rentals in Cleeve Hill

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Top-rated vacation rentals in Cleeve Hill

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Guest favorite

Cottage in Cheltenham

4.9 out of 5 average rating, 416 reviews

The Bothy cottage in the Cotswolds

The Bothy is a conversion of a 17th Century Cotswold stone stable and a 20th Century kennel building. On the ground floor is the living room with a beautiful wood burning stove, a fully equipped kitchen, a comfortable double bedroom and a modern shower room. Whilst upstairs, which is accessed from a narrow oak staircase, you can find the twin bedroom. The living room has been fitted to retain all its original features and is furnished in period style. I have included many Georgian and Victorian pieces and have also included a large settee and two arm chairs, dining table and chairs for 4, corner cupboard and a dash of the 21st Century with a Sky television. The Bothy is beautifully situated in the Postlip Coombe on the leeward side of the Cotswolds highest hill and yet only minutes from Winchcombe, a classic Cotswold "wool" town, renowned for its excellent shops, restaurants and architecture.

Oct 17 – 24

R2,377 ZAR per night

Guest favorite

Shepherd’s hut in Winchcombe

4.97 out of 5 average rating, 124 reviews

Stunning Cotswold Views, Idyllic, En suite TV/WiFi

Scandinavian styled, ensuite, luxury Shepherd's Hut set in idyllic private countryside. Extensive hillside views. Perfectly located in an Area of Outstanding Natural Beauty (AONB) in The Cotswolds. National Walking Trails on the doorstep. Picturesque walk or e-bike to medieval Winchcombe; home to the fascinating & majestic Sudeley Castle, many interesting shops, excellent restaurants, superb cafés & pubs. Just one other beautiful Shepherd’s Hut is also available & both can be booked together.

May 27 – Jun 3

R2,333 ZAR per night

Guest favorite

Guest suite in Winchcombe

4.93 out of 5 average rating, 120 reviews

The Annex Self contained suite on a working farm

A self-contained annex on a working farm in the beautiful Cotswold town of Winchcombe. Sitting above the medieval town, the room has spectacular views of the surrounding cotswold hills. Situated 10 minutes walk from the centre of town with lots of pubs, shops and restaurants. Right on the Winchcombe Way and close to the Cotswold Way its ideal for walkers. Secure cycle storage is also available. Broadway, Stow-on-the Wold, Bourton-on-the -Water Cheltenham, Stratford and Oxford are all drivable

Sep 11 – 18

R1,910 ZAR per night

Guest favorite

Cottage in Prestbury

4.95 out of 5 average rating, 128 reviews

Luxury Thatched Cotswold Cottage, amazing location

Located in a historic village a stone's throw from Cheltenham's racecourse is our immaculately restored thatched cottage. A choice of 3 pubs, local shop and butcher can be found within walking distance. Ideal for 2 couples sharing or a family with accommodation on 2 floors. Featuring a master suite with roll-top bath and own sitting room which can be converted into a bedroom with a double sofa bed. Downstairs an accessible bedroom with its own separate shower w/c. Full kitchen diner with dog bed

Oct 11 – 18

R6,443 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.

Feb 21 – 28

R2,492 ZAR per night

Guest favorite

Home in Woodmancote

4.98 out of 5 average rating, 125 reviews

The Cotswold Holiday Home.

Innisfree was built in 1907 from local Cotswold stone, recently extended and renovated to a high standard with modern contemporary fittings making for a very warm and comfortable holiday home. Bedrooms have been fitted with new beds for flexible accommodation of singles and superking size doubles. A single child’s bed and travel cot may be added to the master suite. A double garage provides parking for two cars. The house has large enclosed gardens with outside furniture and BBQ fireplace.

Oct 12 – 19

R2,984 ZAR per night

Guest favorite

Guesthouse in Leigh

4.92 out of 5 average rating, 154 reviews

Cosy countryside retreat.

The Nest is a self contained detached annexe set in the peaceful Gloucestershire village of The Leigh. The property has been newly refurbished and is available for up to 2 people with access to a secluded garden space within our lovely orchard surroundings. The property has easy access and ample parking. Located within easy reach of Cheltenham, Tewkesbury, Gloucester, The Malverns, Cotswolds and M5, the accommodation is in a perfect position for exploring all that the area has to offer.

Oct 12 – 19

R2,076 ZAR per night

Guest favorite

Cottage in Stanley Pontlarge

4.99 out of 5 average rating, 158 reviews

Stunning Cotswold cottage, log burner, Winchcombe

Gorgeous romantic Cotswold cottage with direct access to walks. Up to 2 well behaved dogs welcome. The Old Mill House is a luxury retreat in Stanley Pontlarge, 2 miles to Winchcombe, 5 miles Cheltenham Racecourse, 9 miles central Cheltenham. Living room with TV and logburner, bedroom with kingsize bed, kitchen with microwave, dishwasher, induction hob, oven Nespresso machine, Smeg fridge/freezer. Shower room. Neal's Yard toiletries. Fast broadband. EV charging. Muddy paw pet washer.

Feb 25 – Mar 4

R3,576 ZAR per night

Guest favorite

Guesthouse in Withington

4.99 out of 5 average rating, 257 reviews

Stylish studio apartment with breakfast hamper.

Nestled in the Cotswold countryside, Pillars Loft offers a hideaway perfect for two, with stylish interiors, modern amenities and luxurious home comforts. Bordering the regency spa town of Cheltenham and the charming market town of Cirencester, Pillars is perfectly located for those looking to enjoy a spot of retail therapy, fine dining or festival scene that Cheltenham is renowned for while also catering for those looking for a peaceful rural retreat.

Mar 6 – 13

R2,921 ZAR per night

Guest favorite

Condo in Gloucestershire

4.97 out of 5 average rating, 149 reviews

Stylish apartment in the heart of Cheltenham

A chic stylish one bedroom apartment in a Victorian townhouse in the centre of Cheltenham with FREE PARKING. Perfectly located to experience all Cheltenham has to offer. A short walking distance to festival locations and the most popular bars and restaurants in Montpellier, The Suffolks, Bath Road and the Promenade. The racecourse is a 25 minute walk or 10 minutes by road. An ideal base for those travelling for business or pleasure.

Aug 8 – 15

R1,867 ZAR per night

Guest favorite

Apartment in Cheltenham

4.83 out of 5 average rating, 291 reviews

Self contained studio apartment close to town

This self contained studio flat is close to the town centre, racecourse, restaurants, nightlife, and countryside. There is off road private parking, a small but fully equipped kitchen and a shower-bathroom. It is ideal for couples, solo adventurers, and business travellers, especially those working on contracts in the area. I provide tea,coffee, milk etc there are also all the basics. Iron and hairdryer are also provided.

Oct 4 – 11

R922 ZAR per night

Guest favorite

Cottage in Withington

5.0 out of 5 average rating, 191 reviews

Boutique 1 bedroom Cotswold Cottage

Kick back and relax in this beautiful location. A stylish stone cottage in the heart of the Coln Valley, arguably the prettiest part of the Cotswolds. The cottage is set within the 16 acres of land belonging to the main house. The perfect place for scenic walks and romantic nights in. A peaceful retreat, just 20 minutes drive from both Cirencester and Cheltenham.

Oct 10 – 17

R3,167 ZAR per night