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, 531 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 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 Prestbury
4.94 out of 5 average rating, 199 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 favourite
The exterior of the cottage is framed by climbing ivy and lush greenery, with stone walls reflecting its historic charm. A wooden dining table is set outside, surrounded by well-maintained flower beds, inviting a pleasant outdoor experience.
Cottage in Stanton
4.96 out of 5 average rating, 112 reviews

Stanton Cotswolds The Hay loft 2 Bed, Cottage

Nestled in the centre of the peaceful and picturesque village of Stanton, in the heart of the Cotswolds, you will find the Hayloft. A charming 17th century converted cotswold stone barn. A light and airy cottage with beams and character. Stanton is quintessentially Cotswolds, picture postcard pretty, providing the perfect getaway from the hustle and bustle of everyday life. The Cotswold Way runs through the village which makes it the perfect base if you enjoy walking, cycling and sightseeing.

Top guest favourite
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, 240 reviews

Little Nook Cottage - Cosy & 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 generous living space features a large stone fireplace with a wood-burning stove at its center. Two comfortable armchairs are positioned adjacent to a spacious sofa, creating a cozy seating area. Soft lighting from table lamps complements the warm tones of the decor.
Cottage in Gloucestershire
4.99 out of 5 average rating, 211 reviews

Chic Georgian town house in Cotswold town centre

Chic luxury town house full of charm with river views. Formerly the town's Post Office, in the heart of Fairford. Three boutique luxury bedrooms, one with master en-suite. Large fully equipped kitchen, generous living space with large fireplace. Pretty, enclosed stone walled garden. We're next door to a lovely 15th century inn with a choice of other pubs nearby; Italian restaurant; local shops; pharmacy; cafes and takeaways on hand - a perfect base to explore this lovely part of the world.

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, 199 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
A feature arched window frames panoramic views of rolling hills and fields, with sunlight illuminating the stone wall and wooden shutters. A vase of fresh flowers sits on a round table, enhancing the inviting atmosphere of the open living space.
Cottage in Saint Briavels
5 out of 5 average rating, 352 reviews

Wye Valley Escape. Romantic Loft on 40-Acre Estate

Romantic luxury loft for two on a 40-acre private estate in the Wye Valley National Landscape. Perfect for honeymooners, stargazers, proposals, anniversaries, or milestone moments. Enjoy panoramic Mork Valley views through the feature arched window, vaulted oak beams, and a cozy fire pit (logs & marshmallows incl.). Includes a generous welcome hamper and exclusive access to our dark skies, meadows, stream, and woodland. A peaceful, magical retreat with high-end, curated experiences available.

Top guest favourite
A cozy sitting area features a stone fireplace with a fire burning warmly. A comfortable armchair, accented with a decorative cushion, faces a wooden coffee table. A stack of books and magazines is neatly arranged on the side, while a small side table displays a drink coaster.
Cottage in Kingham
4.98 out of 5 average rating, 320 reviews

A stylish and cosy Cotswold cottage

A recently renovated, beautifully styled cottage located in the heart of ‘England’s Favourite Village’. A 2 minute stroll will take you to the famous Wild Rabbit Restaurant and the ‘UK’s Dining pub of the year 2019’, The Kingham Plough. A 2 minute drive or 30 minute walk will lead you to another renowned culinary destination, Daylesford Organic Farm Shop, Restaurant and Spa. Famous Cotswold villages surround the area including Stow on the Wold, Burford and Bourton on the Water.

Top guest favourite
A charming stone cottage is framed by lush greenery and colorful flowering plants. A wooden gate leads to a gravel driveway, while rolling hills can be seen in the background under a clear blue sky.
Cottage in Broadway
5 out of 5 average rating, 135 reviews

Hobleys Cottage Stanton Nr Broadway

Hobleys Cottage is positioned on the edge of the historic village of Stanton which is widely regarded as one of the most picturesque in the Cotswolds. Recently refurbished the luxury accommodation is light and spacious with a well-equipped kitchen, open plan dining and sitting room. Wake up to stunning views over the adjoining pasture fields; a relaxing setting and a perfect base from which to explore the Cotswalds. The village pub The Mount Inn is within walking distance.

Top guest favourite
A well-maintained garden features a wooden picnic table in a grassy area, surrounded by neatly trimmed shrubs and flower beds. The exterior of a charming cottage can be seen in the background, with multiple windows and a welcoming front door.
Cottage in Mount Pleasant
4.97 out of 5 average rating, 274 reviews

Traditional Cotswold cottage, Bisley, Nr. Stroud.

The cottage is set within the beautiful Cotswold village of Bisley. It is set out over three floors and comprises of an open-plan kitchen/dining/sitting room with an exposed stone fireplace with woodburner. TV, wifi and a well equipped kitchen. A very steep wooden staircase leads to the first floor with a double bedroom and bathroom/w.c. Another steep staircase leads to the second floor which comprises of a twin bedroom and a bathroom/w.c.

Guest favourite
A modern kitchen features sleek grey cabinetry and polished white countertops. A stainless steel sink is complemented by a built-in wine fridge. Nearby, large glass doors open to a garden area, allowing natural light to illuminate the space. A decorative welcome sign is placed on the countertop.
Cottage in Winchcombe
4.92 out of 5 average rating, 556 reviews

Cotswold77 - Heart of the Cotswolds

Set in the heart of the Saxon village of Winchcombe a beautifully restored and luxuriously furnished Grade II listed cottage set over three floors with a pretty, sunny garden. Glorious countryside, Cotswold country pubs and a Michelin star restaurant all in walking distance. 6 miles from Cheltenham Racecourse and perfect for the Literature, Jazz and Science Festivals in Cheltenham. An Idyllic spot for exploring the Cotswolds!

Top guest favourite
Cottage in Cheltenham
4.93 out of 5 average rating, 167 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 .

Popular amenities for cottage rentals in Cheltenham

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 $76 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Cheltenham holiday rentals include wifi 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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