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Cottage vacation rentals in Cheltenham

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Top-rated cottage rentals in Cheltenham

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Top guest favorite
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, 501 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 favorite
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, 134 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 favorite
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

Guest favorite
A lush garden landscape is visible, featuring neatly trimmed hedges and blossoming apple trees. A soft pink flower in the foreground draws attention to the greenery, while distant hills provide a serene backdrop under a partly cloudy sky.
Cottage in Gloucestershire
4.95 out of 5 average rating, 443 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. Great views from upstairs, lovely private patio with garden/valley views. Free off-street parking. Upstairs, beamed living/bedroom with comfy bed, 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/low pitched ceiling.

Top guest favorite
The living area features a cozy seating arrangement with a neutral-toned sofa and decorative cushions. A natural woven pendant light hangs above, illuminating the space. A rustic coffee table sits on textured flooring, accompanied by warm tones and a charming wreath adorning the entrance.
Cottage in Winchcombe
4.98 out of 5 average rating, 188 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 favorite
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 favorite
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, 203 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!

Guest favorite
A living room is displayed with a stone fireplace as a focal point. A comfortable chair is positioned next to a window seat adorned with cushions. A television rests on a side table, surrounded by a few books. Decorative wall art adds subtle character.
Cottage in Minchinhampton
4.97 out of 5 average rating, 232 reviews

Grade II listed historic Cotswolds cottage

A Grade II listed 2-bedroom cottage, in a charming Cotswolds area, steeped in history and character, with original windows, traditional flagstone flooring, stone walls, oak beams and a fireplace. All rooms have lovely little window seats. Enjoy your own orchard at the end of the garden, perfect for a BBQ or picnic. The Cottage also includes free off-street parking. We love the local walks, views and the quintessential little Cotswolds high street only minutes walk from the cottage.

Guest favorite
A charming row of 18th-century cottages is depicted, featuring stone exteriors with traditional slate roofs. Lush vegetation and climbing plants adorn the walls, while windows invite natural light. The pathway, bordered by vibrant flowers, leads to an inviting garden space that enhances the cottage's appeal.
Cottage in Winchcombe
4.93 out of 5 average rating, 135 reviews

The Feathered Nest an idyllic Cotswolds escape.

Nestled in the heart of historic Winchcombe, The Feathered Nest offers a welcoming escape in the beautiful North Cotswolds—perfect for any season. Set on picturesque Vineyard Street, this lovingly restored former wool cottage blends timeless character with modern comforts. Thoughtfully renovated by your hosts, Paul and Amanda, the boutique two-bedroom home features stylish furnishings and all the contemporary amenities you need for a relaxing stay. Next Availability: 28th October.

Top guest favorite
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 favorite
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, 144 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 favorite
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, 512 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.

Popular amenities for Cheltenham cottage rentals

Quick stats about cottage rentals in Cheltenham

  • Total vacation rentals

    Explore 20 vacation rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham vacation rentals start at G$12,544 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Cheltenham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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