Cottage holiday rentals in Cheltenham

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Top-rated cottage rentals in Cheltenham

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Top Guest favourite
A wide view of rolling green hills displays a tranquil landscape. A small pond is nestled among lush foliage, surrounded by paths cutting through the greenery. Trees are scattered throughout the scene, contributing to the natural beauty of the area.
Cottage in Cheltenham
4.92 out of 5 average rating, 505 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.

Guest favourite
An open-plan living area features exposed wooden beams and a brick feature wall, creating a warm ambiance. A plush sofa is positioned beside a log burner. A glass vase with colorful flowers adorns the dining table, enhancing the inviting interior.
Cottage in Stoke Orchard
4.93 out of 5 average rating, 135 reviews

Willow Cottage, A Luxury Cotswold Retreat

Willow Cottage is a self-contained annexe connected to Waterloo House, a 19th century farmhouse. Named after the Weeping Willow tree right outside the door and located in the beautiful semi-rural village of Stoke Orchard, this recently renovated cottage offers an excellent base from which to explore the Cotswolds. There are great walks and cycle routes straight out of the door, and with Cheltenham Racecourse and Cheltenham town only a short drive away the possibilities for exploring are endless!

Guest favourite
An open plan master bedroom is illuminated by natural light from large windows. A free-standing roll-top bath sits beside the bed, accompanied by a potted plant. Exposed wooden beams add character, while tasteful wall art complements the tranquil decor.
Cottage in Henleaze
4.95 out of 5 average rating, 181 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

Top Guest favourite
The image captures the exterior of a stone farmhouse surrounded by lush greenery. Flowering plants and shrubs add color to the scene, while a white window contrasts with the rustic stone walls. The area features a well-kept grass patch leading up to the structure.
Cottage in Gloucestershire
4.97 out of 5 average rating, 168 reviews

Cottage Nestled within old Cotswold Farmhouse

Take your first glimpse of the rolling fields surrounding our traditional Cotswold stone farmstead, as you travel along our private, tree lined drive. In an AONB, the farmstead sits on the edge of the Golden Valley. Dating back to the 1700s, Little Finch's Cottage is nestled within the original Farmhouse, where you can still find exposed beams and sunny window seats. Step through Little Finch's front door into the lounge/breakfast room which is linked to the bedroom by a steep spiral staircase.

Top Guest favourite
The charming exterior of Little Nook Cottage features a warm stone façade, adorned with holiday decorations. A small evergreen tree with lights hangs above the entrance, and a wreath is positioned on the front door, enhancing the cottage's welcoming appearance.
Cottage in Winchcombe
4.98 out of 5 average rating, 190 reviews

Little Nook Cottage - Dog Friendly & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Top Guest favourite
A charming Cotswold stone cottage is depicted, featuring a stone pathway leading to a warm, inviting entrance. Surrounding greenery enhances the rustic ambiance, while the exterior showcases original details and serene landscaping. Bicycles are securely parked nearby, indicating accessibility for outdoor activities.
Cottage in Painswick
5 out of 5 average rating, 186 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).

Top Guest favourite
The exterior of a charming Cotswold stone cottage is showcased, featuring a slate roof and climbing roses around the windows. A well-maintained garden is visible, with greenery surrounding a patio umbrella. The peaceful setting is enhanced by a wooden fence in the foreground.
Cottage in Selsley
4.99 out of 5 average rating, 206 reviews

Charming one bed detached cottage in the Cotswolds

Beautiful 17th Century detached Cotswold stone cottage, renovated and furnished to a high standard, located off a quiet country lane with far reaching views, a parking space and patio area. The open plan ground floor looks across the hosts cottage garden, has many original features including a traditional stone fireplace with wood burner, exposed beams and feature walls. The oak staircase leads to the bedroom and bathroom and fabulous views can be enjoyed across the valley. A little gem!

Top Guest favourite
Cottage in Gloucestershire
4.99 out of 5 average rating, 295 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.

Guest favourite
A spacious bedroom is presented with light grey walls and soft carpeting. A large white bed is centered in the room, accented by grey pillows and a decorative throw. A seating area features a teal sofa and a light fixture hangs from the ceiling.
Cottage in Henleaze
4.93 out of 5 average rating, 147 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.

Guest favourite
The charming exterior of a detached cottage is framed by lush greenery. Light stones contrast with a wooden gabled section, while flower pots filled with plants sit along the pathways. Windows allow natural light to fill the interior, creating an inviting first impression.
Cottage in Stroud
4.93 out of 5 average rating, 513 reviews

Stunning Private Cotswold Cottage with views

Hope Cottage is cosy, quirky and full of character (lots of exposed stone walls and original beams, plus a woodburner) but with all mod cons. It sits in its own terrace/garden in this pretty South Cotswolds village. There are wonderful views, and it's the perfect place to relax and get away from it all. A true home from home, with privacy and seclusion (no owners on site) and walks in all directions.

Top Guest favourite
The entrance to the stables features a modern grey door with a welcoming sign. A brick pathway leads to the entrance, flanked by wooden support beams and lush greenery, creating an inviting approach to the accommodation.
Cottage in Henleaze
4.93 out of 5 average rating, 155 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 .

Top Guest favourite
The exterior of Heron Cottage is shown, featuring a stone facade and a charming terrace. Two green chairs and a small table are positioned on the patio, set against a backdrop of well-maintained grass and trees, creating a serene outdoor space.
Cottage in Rendcomb
5 out of 5 average rating, 402 reviews

Stunning 2 bed Cotswold cottage, sleeps 4

Formally a candle making workshop and then the village surgery, Heron Cottage has recently been completely refurbished and extended to create a modern, light and comfortable cottage. Sitting in beautiful countryside and conveniently located between Cheltenham and Cirencester, the cottage is perfect for romantic breaks and those that want to escape from busy city life.

Popular amenities for Cheltenham cottage rentals

Quick stats about cottage rentals in Cheltenham

  • Total holiday rentals

    Explore 20 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $106 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Cheltenham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cheltenham rentals

  • 4.8 Average rating

    Cheltenham stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Cheltenham's top spots, include Cheltenham Racecourse, Pittville Park, and Everyman Theatre

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