Family-friendly vacation 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, 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 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, 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!

Superhost
A modern kitchen space features sleek white cabinets and an integrated oven. A wooden countertop provides an inviting area for meal preparation, while stainless steel appliances complement the clean design. Natural light enters through a nearby window, enhancing the bright and functional atmosphere.
Condo in Henleaze
4.88 out of 5 average rating, 351 reviews

Modern studio in the heart of Cheltenham

Enjoy your stay in this centrally located studio apartment on the top ( second ) floor. Ideally located for all the wonderful bars cafes and restaurants that Cheltenham has to offer, this easy living, modern studio apartment is on the doorstep to all the activity. You will see instructions for entry 48 hours before arrival. GL52 2SQ There is a secure side door for bike storage on ground floor. Cheltenham Racecourse is a 5 minute drive ( traffic dependent ) or a 30 minute walk from apartment.

Guest favourite
A charming outdoor seating area is positioned in front of a brick structure, featuring large windows. The path is bordered by neatly trimmed shrubs and vibrant green plants, inviting guests to relax in the black wicker chairs set on a paved surface.
Barn in Bushley
4.93 out of 5 average rating, 294 reviews

Courtyard at Hither Ham House, Stunning retreat

Welcome to the Courtyard at Hither Ham House, a stunning little hideaway. Relax in the King size Bed and enjoy the peaceful setting on offer, it has a fully equipped Kitchen with Breakfast bar and the sofa bed can accommodate one extra person. Private entrance and parking on site don't forget to bring your rackets as free use of the Tennis Court is available. Highspeed internet is included and enjoy an alfresco drink outside. Easy access for Cotswolds, Cheltenham, Tewksbury and Upton upon Severn

Top 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.
Apartment in Henleaze
4.88 out of 5 average rating, 165 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 homes in Gloucestershire
4.93 out of 5 average rating, 725 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.

Guest favourite
A private garden studio is shown alongside a manicured garden, featuring a stone pathway lined with soft grass. Contemporary wooden fencing provides privacy, while a small tree adds a natural touch. Seating areas with chairs are visible, inviting outdoor relaxation.
Guest suite in Henleaze
4.89 out of 5 average rating, 122 reviews

Detached Garden Room in Cheltenham

Beautiful private garden studio, perfect for a couple for the races or weekend in Cheltenham or the Cotswolds. Continental breakfast included on the first day. Enjoy visiting one of the famous Cheltenham festivals. Private entrance with parking, patio, table & chairs. Opposite a great pub. 3.2 miles/9mins from Cheltenham racecourse. The hosts are very welcoming & are on hand to help with restaurant or bar recommendations. There’s so much to see & do in Cheltenham & the surroundings area.

Top guest favourite
A bright studio space is furnished with a wooden bed draped in white linens and a teal throw. A cozy sofa is positioned beside a TV, with a small kitchenette featuring modern amenities. Natural light illuminates the area through large windows that overlook a garden.
Guest suite in Henleaze
4.99 out of 5 average rating, 152 reviews

Bright spacious private annex in a great location

Bright and spacious private recently built self-contained annex within a friendly family home. Ideal quiet location, close to town, local amenities, bars and restaurants. Close to Bath Road, bus stops, hospital and train station. Separate entrance with key safe entry. Small new kitchen area with hob, fridge, microwave and kettle. Lounge area has large comfy sofa and TV. Views into a large garden with own seating on the decking. Comfy bed, own bathroom with shower. Off road free parking.

Top guest favourite
The kitchen area features a light marble countertop with a sink, complemented by modern pendant lighting. In the background, a cozy living room is visible, furnished with a dark sofa and colorful cushions, highlighted by natural light from large windows.
Apartment in Henleaze
4.93 out of 5 average rating, 321 reviews

The Best address in Montpellier, Cheltenham

This wonderfully spacious apartment is situated in the heart of fashionable Montpellier where you will find an incredible array of Independent shops and prestigious eateries such as The Ivy ,Giggling Squid , The Daffodil and the renowned Michelin starred Le Champignons Savage,a new find is Kibousushi located about 200 metres from the apartment ,a new find for us and an amazing Japanese restaurant ,but you have to book in advance . The home of horse racing is just a 20 minute walk .

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.
Guesthouse in Henleaze
4.91 out of 5 average rating, 357 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.

Superhost
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, 357 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 a small wooden studio features a large window with a view of the surrounding countryside. A bench is positioned near a gravel path. The lawn is neatly maintained, leading to a wooden gate with a paddock visible in the background.
Guesthouse in Worcestershire
4.95 out of 5 average rating, 243 reviews

Cleeve Cottage (The Studio)

A small detached studio/annex, in the picturesque village of Bushley, ideal location for anyone looking to have a short break in the countryside just 1.5 miles from the old market town of Tewkesbury and only 20 minutes from Cheltenham so perfect for a weekend at the races. Plenty of stunning rural locations to be explored nearby, with easy access to the beautiful Malvern hills, fantastic for cycling and hiking

Popular amenities for Tewkesbury Borough family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Tewkesbury Borough

  • Total vacation rentals

    Explore 1,540 vacation rentals in Tewkesbury Borough

  • Nightly prices starting at

    Tewkesbury Borough vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 61,520 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 600 rentals that welcome pets

  • Vacation 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 vacation 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