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.

%{current} / %{total}1 / 1
Top guest favourite
The kitchen and dining area showcase a modern design with a central island and three bar stools. A dining table is set with place mats, and a bowl is featured at the center. Black cabinetry, stainless steel appliances, and natural light create a welcoming ambiance.
Home in Chester
4.99 out of 5 average rating, 149 reviews

STUNNING 3-BED PARKING GARDEN FANTASTIC LOCATION

Located in the popular suburb of Handbridge this newly refurbished property is a short distance from the city centre. The racecourse, theatre & history galore are all a short stroll away. Despite this the property is situated on a quiet no through road, boasts off road parking for 2 cars and a very pleasant garden. The house sleeps 6 with 2 double beds and large bunks in the third bedroom. A travel cot is also available on request. Full fibre broadband and some daily essentials are included.

Guest favourite
Home in Mouldsworth
4.97 out of 5 average rating, 239 reviews

Luxury stay near Chester with hot tub and land

@ForestStablesHolidays is situated in a sought after quiet village and set in over 3 acres of private landscaped gardens & land, with undisturbed views across open farmland. It is a beautifully presented detached barn conversion with outstanding accommodation and superb spec throughout. Recently renovated to the highest standard, the property offers luxury accommodation within walking distance to the renowned gastropub, The Goshawk and train station, offering a service to Chester within 10 min.

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, 379 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 charming barn conversion is depicted, featuring a light-colored exterior with green doors. Large windows allow natural light to fill the space. Surrounding greenery and textured gravel create a welcoming outdoor area, complemented by dappled shadows from overhead trees.
Barn in Cheshire West and Chester
4.92 out of 5 average rating, 101 reviews

Hampton Bye Barn, Rural Retreat

Located within the heart of the stunning Cheshire countryside just minutes from the Sandstone Trail and only 20 minutes to the historic Cathedral City of Chester. Relax in this spacious barn conversion with beautiful views of both the Bickerton and Welsh Hills, with plenty of outdoor space to enjoy, including a heated swimming pool for a relaxing dip! The local area is bursting with activities for families or alternatively there is plenty of peaceful countryside to enjoy at your leisure.

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, 201 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.

Guest favourite
Barn in Little Budworth
4.98 out of 5 average rating, 373 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
A warm dining area is featured, highlighting a wooden table surrounded by six chairs. A charming wood burner is positioned within a brick fireplace. Bookshelves filled with books line one wall, and natural light enters through a window dressed with light curtains.
Cottage in Christleton
4.95 out of 5 average rating, 219 reviews

Charming Canalside Cottage

Our comfortable cottage has easy access into the heart of Chester. The garden gate opens onto the canal towpath with a ten minute stroll up to our local Cheshire Cat pub. Alternatively, stay in and snuggle up with the wood burner. On a fine day, turn left out of the back gate for a pleasant 35 minute walk, following the canal directly into the beautiful city of Chester. Maybe take a boat trip on the river Dee? Alternatively, Chester Zoo is just a 10 minute drive, continuing down the A41.

Top guest favourite
A modern kitchen is displayed, featuring sleek cabinetry and essential appliances. A bar with two stools is positioned adjacent to the countertop. A microwave, oven, and hob are integrated within the cabinetry, complemented by a contemporary sink and ample workspace.
Flat in Chester
4.97 out of 5 average rating, 346 reviews

34 Cuppin St Luxury Chester City Centre apartment

Modern luxury apartment set within the heart of Chester City Centre walls. Set within a quiet cobbled street, the apartments central location provides access to all Chester has to offer all within a short walking distance away. The apartment has one very comfortable double king size bed, a modern bathroom with shower, WC and basin and a kitchen with hob, microwave, oven, dishwasher, fridge and all crockery and utensils for your use. Smart TVs are installed to the living area and bedroom.

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, 125 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.

Top guest favourite
A large, bright living room features two curved sofas with neutral upholstery, facing a dark round coffee table. A projector screen is mounted on the wall, surrounded by illuminated shelving. Natural light filters through the window, highlighting the room's modern design.
Apartment in Chester
4.95 out of 5 average rating, 105 reviews

Penthouse with stunning views/Parking/Private chef

A perfectly located Penthouse apartment You will fall in love with the Penthouse, it's a gem, here's why: * Penthouse apartment with panoramic views of Chester Racecourse/Welsh hills * Central location within walking distance of everything * Secure, gated parking * Large, bright living room with projector screen - perfect for a movie night in * king size bedrooms, super comfy beds (both with its own bathroom) * Free standing bathtub with views on to Chester Racecourse

Popular amenities for Chester family-friendly rentals

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$171 SGD$194 SGD$206 SGD$223 SGD$244 SGD$242 SGD$257 SGD$258 SGD$236 SGD$232 SGD$221 SGD$246 SGD
Avg. temp5°C5°C7°C9°C12°C15°C17°C16°C14°C11°C8°C5°C

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!

Destinations to explore