Family-friendly holiday rentals in Chester

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chester

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

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Guest favourite
A charming red-brick end terrace cottage is depicted, showcasing Victorian architectural details. Large front windows adorned with flower boxes invite natural light. A small front garden with a white fence complements the inviting facade, and a parked car is visible on the quiet street.
Cottage in Chester
4.97 out of 5 average rating, 179 reviews

Idyllic Cottage, Hot Tub, Parking, 5 Beds Sleeps 8

The Old Post Office is the best of both worlds, an idyllic cottage feel but only 5 mins drive or 20 mins walk from Chester city centre, the train station and the racecourse. 4 good size bedrooms with 5 beds, 1 king, 2 doubles and 2 singles, lounge with open fire, dining room. Bathroom with freestanding bath and separate shower, a second WC and shower room on the ground floor, a well equipped kitchen with dining area and a delightful south facing garden with a hot tub, there is plenty of room.

Top guest favourite
An open plan sitting and dining area features exposed wooden beams and a large, rustic fireplace. A comfortable, neutral-colored sofa is complemented by an armchair, and a small coffee table sits at the center. Natural light filters in through a window, enhancing the cozy ambiance.
Cottage in Chester
4.92 out of 5 average rating, 375 reviews

Characterful City Centre Cottage, Garden & Parking

King Street is a charming cobbled street nestled in the heart of the city centre. Situated within the beautiful City Walls, guests will be able to access all that Chester has to offer including shops, restaurants, historic architecture and so much more. 29 King Street is a former Blacksmiths Cottage dating from 1773 so the property is full of character with a fascinating history. A peaceful retreat and a superb base for exploring our wonderful city, we hope everyone will enjoy their time here.

Top guest favourite
A bright dining area features a wooden table surrounded by light-colored furniture. A plant adds a fresh touch, while soft lighting creates a welcoming ambiance. The space is accentuated by large windows allowing natural light and a decorative mirror enhancing the room's depth.
Townhouse in Chester
4.98 out of 5 average rating, 181 reviews

Luxury townhouse within the City walls

No 6 is right in the heart of Chester. All the sights of Chester are just a short stroll away. The racecourse, river, cathedral and all the shops, coffee stops and restaurants are so easy to reach. However the location just off the main street still provides privacy given such convenience. No 6 has been recently renovated to the very highest specification including a hand made kitchen and many hand made furnishings. All the linens are luxurious aimed at making your stay a really special one.

Top guest favourite
The exterior of a historic brick building showcases intricate patterned tilework and distinctive architectural features. Large, mullioned windows punctuate the facade. A pathway leads to the entrance, bordered by lush greenery, reflecting the building's charming character and connection to its surroundings.
Home in Chester
4.94 out of 5 average rating, 382 reviews

Stunning Church Lodge next to City Centre

Recently refurbished this beautiful Grade 2 Listed building is located in Handbridge a very short walk from Chester City Center, the city walls and the River Dee. The house was completely renovated in 2018 to a very high standard with a beautiful bathroom including a roll top bath and shower and modern kitchen including dishwasher, coffee machine and breakfast bar. Built in 1887 the house was designed by the famous architect John Douglas and was previously owned by the Duke of Westminster

Top guest favourite
A stylish seating area features a light grey chair adorned with a yellow pillow, positioned near a wooden door. A black shelving unit holds decorative items and a TV, while warm wooden flooring complements the space.
Townhouse in Chester
4.92 out of 5 average rating, 147 reviews

Townhouse in trendy suburb of Hoole

A stylishly decorated 2 bedroom terraced home in Hoole with free on-street parking. Its proximity to Chester Town Centre, the railway station and the vibrant suburb of Hoole make this an ideal location for your visit to historic Chester. Hipster bars and pubs, great gastro bistros, local parks are all within walking distance of the house. A 10/15 minute walk into historic Chester town for cathedral visits, shopping and beautiful river front. Driving distance to Cheshire Oaks and Chester Zoo.

Top guest favourite
A spacious private garden features a hot tub surrounded by lounge chairs and small hedged shrubs. A wooden table with umbrella is visible, along with a cozy seating area. The sunlit scene offers a relaxing outdoor space ideal for enjoyment and leisure.
Cottage in Chester
4.99 out of 5 average rating, 203 reviews

Stunning Views, Hot Tub, 5 minutes to Chester

Pipers Ash is a quaint small hamlet surrounded by green belt, set at the highest point of Chester next to the historical millennium beacon. Perfectly situated just two miles from the beautiful historic Chester city centre. Take a short car ride or just half an hours walk. Chester Zoo is just five minutes drive away. There are many lovely country walks and of course some fabulous country pubs. The trendy suburb of Hoole is only 15 minutes walk. Here you will find bars restaurants and shops.

Top guest favourite
A private courtyard is showcased, featuring a sheltered seating area with comfortable furnishings and a cozy table set for outdoor dining. String lights create a gentle ambiance, complementing the rustic brick backdrop and inviting relaxation in the tranquil space.
Cottage in Coddington
4.97 out of 5 average rating, 142 reviews

Luxury Renovated Barn Conversion

Relax in this calm, stylish space. Sitting beautifully in its picturesque setting, in the grounds of the Old Rectory (occupied by your hosts). A handsome 3 bedroom barn, renovated to the highest standards, a comfortable home for 5 guests and up to two well behaved dogs. Located in a peaceful rural hamlet, it's the perfect place to get away from it all, with country walks and cycles on your doorstep. Only a 20 minute drive from Chester and easily accessible for Manchester and Liverpool.

Guest favourite
Barn in Little Budworth
4.98 out of 5 average rating, 377 reviews

The Barn at Oulton Smithy

Beautiful barn retreat with options for ~ spa treatments/massages ~ private chef Ideal for couples, families or friends in the grounds of historic Oulton Smithy. Close to Oulton Park race circuit in the pretty Cheshire countryside. The barn is set back from the Smithy with its own entrance and a stunning private hot tub. Lots to do while you’re here…massages, aromatherapy, pilates, gin making workshops, private dining all available in the barn (additional cost) Luxury touches throughout

Top guest favourite
The living area showcases a stylish arrangement with a tufted sofa and leather armchairs. Two side tables hold decorative lamps, while natural light floods in through large glass doors that open to a patio, enhancing the connection between indoor and outdoor spaces.
Townhouse in Chester
5 out of 5 average rating, 117 reviews

Historic City Centre Town House

Heritage House offers you comfort and vintage style in the historical heart of Chester. Located within walking distance to tourist attractions, Racecourse, restaurants & pubs. The newly refurbished property provides boutique quality accommodation for up to 6 guests in 3 double bedrooms & 3 bathrooms; an open plan kitchen living area with diner. The patio garden as an extension of the living area creates an enjoyable outdoor experience. We look forward to welcoming you at Heritage House!

Guest favourite
An open-plan living area features a stylish sofa facing a modern fireplace with a marble surround. Natural light floods the space from skylights and large glass doors, leading to an outdoor terrace. A contemporary dining area with dark cabinetry is visible in the background.
Home in Chester
4.91 out of 5 average rating, 145 reviews

Luxury central townhouse, Cinema/Private chef

Without a doubt one of the best properties in Chester! You will fall in love with this home, it's a gem and here's why: * Central location within walking distance of everything * Huge social spaces with a large kitchen and dining area and a separate living room (With smart TV and Sky TV) * Cinema room * Free parking in a secure pin pad operated garage * Outdoor terrace area * Make up room * 3 king size bedrooms * Private chef on request to create a bespoke in house dining experience

Top guest favourite
An open plan dining area features a wooden table set for a meal, accommodating six people. A potted olive tree adds a touch of greenery. Natural light illuminates the space, highlighting the contemporary art piece on the wall and the texture of the soft rug beneath.
Home in Chester
4.94 out of 5 average rating, 126 reviews

Luxury City Centre Townhouse

A unique home, centrally located in the vibrant city of Chester. The Victorian townhouse has been newly renovated to a high standard, giving it a luxury feel with plenty of space. Original features and character have been sympathetically restored, maintaining its charm with a modern twist. This house really does offer a fantastic location next to the Grosvenor Park and in close proximity to shops, coffee shops, restaurants, bars, Chester racecourse, and the Roman Amphitheatre.

Guest favourite
Townhouse in Chester
4.91 out of 5 average rating, 349 reviews

Beautiful home. Sleeps 4. Prime central location!

Excellent choice for a Chester City break this year. Fresh and welcoming enjoy with friends or family. 💛 This Grade II Listed 3-storey town house is one of the closest residential homes to the centre & Race Course. Features have been sympathetically restored and the elegant décor adds to its appeal. Walking distance of Chester train station, shops, restaurants & city centre. A complimentary hamper including milk and goodies with every booking.

Popular amenities for Chester family-friendly rentals

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Avg. price$171 SGD$194 SGD$206 SGD$223 SGD$244 SGD$242 SGD$256 SGD$258 SGD$236 SGD$232 SGD$221 SGD$246 SGD
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Quick stats about holiday rentals that are family-friendly in Chester

  • Total holiday rentals

    Explore 430 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 25,450 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wifi availability

    420 of Chester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chester rentals

  • 4.8 Average rating

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

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