Cottage vacation rentals in Cheltenham

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Top-rated cottage rentals in Cheltenham

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Guest favorite

Cottage in Cheltenham

4.9 out of 5 average rating, 417 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 22 – 29

G$26,206 GYD per night

Guest favorite

Cottage in Gloucestershire

4.95 out of 5 average rating, 334 reviews

Cotswold cottage with views in Nailsworth

Apple Tree Cottage is an airy, yet cosy 1 bed studio cottage. Great base for exploring Cotswolds. Many local hiking opportunities. Amazing views from upstairs, lovely private patio with garden/valley views. Free off-street parking. Comfy bed. Upstairs, beamed living /bedroom with Smart TV& WiFi. Downstairs, well equipped kitchen-diner, shower room/toilet. 10-15min walk to Nailsworth centre with many eateries. Unfortunately unsuitable for those with mobility issues due to stairs/pitched ceilings.

Jan 6 – 13

G$17,738 GYD per night

Guest favorite

Cottage in Wellington Heath

4.99 out of 5 average rating, 218 reviews

Wonderful cottage with glorious views

The Garden Studio is a luxury contemporary retreat in the grounds of our Arts and Crafts home with wonderful views across Herefordshire countryside. Located 1 mile from the market town of Ledbury and its independent shops and cafes, it is within striking distance of the Malvern Hills and the Wye Valley (Areas of Outstanding Natural Beauty). Festivals nearby are Ledbury Poetry, Hay, Longborough Opera, Cheltenham, Three Counties/Choirs. Piano & dedicated work station for those wanting to WFH here!

Mar 18 – 25

G$25,083 GYD 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 17 – 24

G$71,047 GYD per night

Guest favorite

Cottage in Winchcombe

4.84 out of 5 average rating, 156 reviews

Penny Cottage - Cosy Cotswold cottage

Penny Cottage is in the heart of the former Saxon town of Winchcombe. It is a traditional Cotswold cottage with a working inglenook fireplace. It is on the Cotswold Way and has access to miles of country walks. Sudeley Castle, the resting place of the only Queen of England to be buried outside a royal palace, is within walking distance. A variety of pubs and restaurants can all be found within a 5 minute walk. The town also boasts a variety of independent shops, and two small supermarkets.

Jan 26 – Feb 2

G$26,840 GYD per night

Guest favorite

Cottage in Painswick

5.0 out of 5 average rating, 132 reviews

Quiet grade 1 listed entire cottage in Cotswolds

A bright and recently modernised grade 1 listed Cotswold stone cottage, 100 yards from the Cotswold Way with breathtaking views down the Stroud Valley, its own parking and secluded outdoor eating. Filled with natural light, it is very peaceful and extremely comfortable with luxury bedding (super king or twin bed) and kitchen. An idyllic spot for walking, cycling, exploring the local scenery or simply escaping the city Painswick is 10 minutes from Stroud ( 87 mins hourly train to London).

Nov 13 – 20

G$40,684 GYD per night

Guest favorite

Cottage in Winstone

4.96 out of 5 average rating, 159 reviews

Cotswold retreat. Spacious and peaceful

This rural retreat provides spacious, contemporary and comfortable accommodation with fabulous views. An open plan ground floor leads to a south facing terrace (sole use.) Upstairs there is a huge bedroom ( Super King bed) and a roll top bath with garden view. Additional shower/WC. Private parking. Hosts on hand if required. This peaceful rural village is an ideal base to explore the Cotswolds and soak up glorious countryside. Enjoy excellent walking and cycling straight out of the door.

Jul 2 – 9

G$27,177 GYD per night

Guest favorite

Cottage in Bank Farm Barns

4.99 out of 5 average rating, 400 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 14 – 21

G$31,664 GYD per night

Guest favorite

Cottage in Gloucestershire

4.99 out of 5 average rating, 248 reviews

53 Church Street - 500 yr old cottage/Luxury/View

53 Church Street served as a corner shop for many years, still evidenced by the door sign. It is likely to be around 500 years old, and has been lovingly restored to re-create an unmistakably historic building with all the modern comforts you could possibly want in a holiday home. From a four poster bed to a sleek, modern bathroom, from a beamed, cosy lounge to a characterful kitchen, and from a winding oak staircase to a breathtaking view of the spectacular Abbey.

Feb 23 – Mar 2

G$33,502 GYD per night

Guest favorite

Cottage in Gloucestershire

4.98 out of 5 average rating, 308 reviews

The Potting Shed, 5* ❤︎ Luxury escape Cirencester

The Potting Shed is the quintessential 5* Cotswold escape. Following an 18 month restoration completed in May 2019, this stone barn conversion is the perfect retreat. Located within the grounds of an elegant Grade II listed Georgian town house on Cecily Hill - voted one of the prettiest streets in England, this romantic getaway is accessed by a private stone bridge which leads through through a formal kitchen garden to a stunning private terrace.

Apr 7 – 14

G$39,899 GYD per night

Guest favorite

Cottage in Gloucestershire

4.94 out of 5 average rating, 109 reviews

Cheltenham - Cosy Bath Road Cottage

A beautifully presented cosy and welcoming, newly refurbished, 2 bedroom Georgian cottage located just off the desirable Bath Road. The local area has plenty of great shops, restaurants and pubs. In addition, trendy Montpellier is a short walk away. The historical spa town of Cheltenham, in the centre of the Costwolds, has a buzzing atmosphere and hosts many events throughout the year, with the famous racecourse is only a 10 minute drive away.

Oct 13 – 20

G$25,831 GYD 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

G$40,360 GYD per night