Family-friendly holiday rentals in Tewkesbury Borough

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Top-rated family-friendly rentals in Tewkesbury Borough

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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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, 507 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, 137 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!

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
4.97 out of 5 average rating, 197 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!

Guest favourite
A colorful armchair with patchwork fabric is positioned beside a slender lamp, creating a cozy reading nook. A tall window allows natural light to illuminate the space, complemented by light sheer curtains. A small side table and decorative elements add charm to the inviting room.
Flat in Henleaze
4.87 out of 5 average rating, 183 reviews

Stunning Regency flat with parking town centre

This Beautiful Regency 1 bed apartment with 1 parking spot (available from 4pm check in to 12 noon check out please) is suitable for adults only. House is situated within walking distance of Cheltenham racecourse, all shops, parks, restaurants and theatres. It has been recently been refurbished . Lovely new carpets and furniture throughout…. Sitting room, kitchen are on one floor with a fabulous double bedroom and a lovely luxury bathroom with shower and large bath tub on the top floor.

Top guest favourite
The entrance to the Garden House is framed by a sturdy tree and vibrant potted plants, showcasing colorful flowers. A wooden table and shelf stand beside the door, enhancing the welcoming appearance of this independent annex.
Tiny home in Gloucestershire
4.93 out of 5 average rating, 738 reviews

The Garden House in Kingsholm, Gloucester

The Garden House is a lovely single room annex with independent access, en-suite bathroom and shower. Light, cosy, and simply furnished, set in the garden of a residential home near the centre of Gloucester, it's a quiet space to relax or work. Driveway parking available. A two-minute walk to the famous Kingsholm rugby stadium and food shops, ten minutes to city centre, bus and train stations, cathedral, Quays shopping outlet, restaurants and historic docks. Easy bus route to Cheltenham.

Top guest favourite
A charming brick exterior showcases the annexe, surrounded by well-maintained greenery. The sloped roof and wooden door complement the rustic feel. Flowering plants in colorful pots are positioned near the entrance, and a gravel path leads to the entrance, inviting relaxation in a serene setting.
Guest house in Leigh
4.91 out of 5 average rating, 245 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.

Guest favourite
A peaceful outdoor view showcases a large grassy area bordered by wooden fencing. A small building is visible on the left, with trees lining the background and much of the foreground free of clutter. Potted plants can be seen near the entrance.
Guest suite in Twyning
4.8 out of 5 average rating, 313 reviews

The groomsroom

Ex - grooms room, in the grounds of a beautiful country mansion. Self contained bedsit/studio with parking. Stabling available at extra cost if you want to turn this into an equine holiday! 4 miles from Tewkesbury and on the outskirts of Twyning, a beautiful location for a country break. Seasonal breakfast ingredients provided, but we are afraid you'll have to cook them yourself! Tea and coffee making facilities also provided. Fresh milk and bread will be in the fridge when you arrive.

Top guest favourite
An outdoor garden area is featured, showcasing a stone patio with a large dining table surrounded by chairs. Potted plants and lush greenery create a natural setting, while the rustic wooden structures of the property provide a charming backdrop.
Guest house in Cranham
4.97 out of 5 average rating, 215 reviews

The Organic Cotswolds Cowshed

The Organic Cotswolds Cowshed Set in the heart of The Cotswolds, one of the most beautiful areas in the UK, we are offering the most organic and toxic free environment that we can for our guests which may be important to you if you are allergic or intolerant to such things as added fragrance to laundry soap or the chemicals used in non-bio cleaning chemicals and sprays. I also have a shepherds hut on the property that sleeps two. See my other listing 1 DOG welcome. No other pets

Top guest favourite
The exterior features a newly refurbished annexe with a clean, modern design. A stone pathway leads to a private entrance, surrounded by gravel and paving. A small area of artificial grass and a garden shed are visible, providing a welcoming outdoor space.
Guest house in Henleaze
4.92 out of 5 average rating, 365 reviews

Beautiful Self-Contained Annexe in Cheltenham

A lovely, newly refurbished annexe, perfect for 1 or 2 guests within good distance to the town center. A cosy, fully functioning, self-contained home from home featuring a double bed, kitchenette, en suite bathroom, 32" TV, heated floor and radiator with a private entrance. Located a 30 minute walk from the town centre and the Brewery Quarter, which is full of restaurants and bars, 2 cinemas, Mr Mulligans Adventure Golf and Hollywood Bowl.

Guest favourite
A spacious room features a comfortable king-size bed covered with a textured yellow quilt. A kitchenette is visible in the background, alongside a wooden table. Natural light enters from a nearby window, illuminating the simple decor, which includes a dresser and casual seating.
Guest suite in Henleaze
4.87 out of 5 average rating, 363 reviews

The Garden retreat

The Garden room has its own front and back door, and access to a lovely south facing garden. It has a kitchenette and en suite. It has a very comfortable king-size bed. We are 10-15 minutes walk from the town centre and have views onto Cleeve Hill the highest point of the Cotwolds. There are good local pubs, a national award winning fish and chip shop and a supermarket all nearby. Perfectly situated for all Cheltenham festivals.

Top guest favourite
The exterior of the converted barn is showcased, featuring rustic red brick walls, a slate roof, and wooden doors. A gravel pathway leads to the entrance, surrounded by greenery and a garden area visible in the background. Skylights are positioned on the roof, allowing natural light.
Barn in Gloucestershire
4.98 out of 5 average rating, 125 reviews

Beautiful Barn in the Cotswolds

Beautifully private converted barn in the heart of Gloucestershire, perfectly situated for Cheltenham Races, the Cotswold Way and Gloucester Rugby as well as all the local town festivals. Dating back to the 1850s and part of the original village Rectory, the barn was converted in 2019 and provides both a light and airy base as well as a cosy and super comfortable retreat. Can sleep up to 4.

Guest favourite
A spacious bedroom features a king-sized bed with white linens and decorative pillows. Natural light enters through multiple windows, illuminating the room. A comfortable chair and side table are positioned nearby, adding to the cozy ambiance. Soft colors complement the serene atmosphere.
Flat in Henleaze
4.85 out of 5 average rating, 341 reviews

Private flat, close to town centre with parking

A large well appointed and spacious double bedroom, with ensuite bathroom, fully equipped kitchen diner and private entrance. This apartment is totally self contained with off road private parking and is only a 15-20 minute walk into the town centre. A fantastic base for exploring the Cotswolds, or just enjoying the festivals and shopping that Cheltenham has to offer.

Popular amenities for Tewkesbury Borough family-friendly rentals

When is the best time to visit Tewkesbury Borough?

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Avg. price$236 SGD$232 SGD$323 SGD$260 SGD$272 SGD$274 SGD$287 SGD$291 SGD$269 SGD$255 SGD$263 SGD$269 SGD
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Quick stats about holiday rentals that are family-friendly in Tewkesbury Borough

  • Total holiday rentals

    Explore 1,540 holiday rentals in Tewkesbury Borough

  • Nightly prices starting at

    Tewkesbury Borough holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 61,520 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 600 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    600 properties have a dedicated workspace

  • Wifi availability

    1,510 of Tewkesbury Borough holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Tewkesbury Borough rentals

  • 4.8 Average rating

    Tewkesbury Borough stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Tewkesbury Borough’s top spots include Cheltenham Racecourse, Sudeley Castle and Cotswold Farm Park

Destinations to explore