Family-friendly holiday rentals in Chiltern

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Top-rated family-friendly rentals in Chiltern

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

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Top guest favourite
The exterior of the stylish studio showcases a charming brick façade, accentuated by climbing vines and colorful flower pots. A small outdoor seating area features a wooden table and chairs, set against a backdrop of lush green grass and well-maintained gardens.
Loft
4.99 out of 5 average rating, 104 reviews

The Nest, a cosy, stylish annex loft

Kick back and relax in this quiet, stylish, self contained studio. Cosy, well-equipped and environmentally friendly, this 1st-floor annex is situated in the Chiltern village of Bellingdon, just North of the market town of Chesham. The perfect location for those exploring the Chilterns, designated an ‘Area of Outstanding Natural Beauty’ walking, cycling or for those working locally, away from their home. The name is inspired by the 50+ species of bird found locally, including the Red Kites.

Top guest favourite
The bright living area features vaulted ceilings with original wooden beams and skylights. A comfortable sofa sits beside a soft ottoman, while a white coffee table holds decorative items. Large glass doors lead to an outdoor space, and a wall-mounted TV is positioned for viewing.
Barn
4.97 out of 5 average rating, 321 reviews

Beautiful cosy Scandi-barn in Chiltern market town

A beautiful, calm and cosy space designed to feel like a home from home. Lovingly updated and modernised, whilst retaining original character and features to create a unique guest experience. Uber-clean and free from clutter, everything looks & feels fresh for each stay. The kitchen, carpets, paintwork, doors, windows and VELUX roof-lights have been replaced or updated recently. Located with a parking space in a secure, gated courtyard just moments from the town centre of Princes Risborough.

Guest favourite
The interior features exposed wooden beams and a charming blend of rustic finishes. A small kitchenette is visible alongside an ensuite wet room with a door. Stairs lead to a raised sleeping area, providing a cozy atmosphere.
Bungalow
4.93 out of 5 average rating, 121 reviews

Entire Converted Coach House

This unique place has a style all its own. The lounge boasts an impressive vaulted celling with magnificent ancient beams, an extremely comfortable sofa bed, and large flat-screen TV (with Apple TV, Netflix and Prime Video) Adjacent is a mini kitchen containing the essentials and a stylish modern ensuite wet room, with shower sink and toilet Stairs lead up to a mezzanine with double mattress and stunning view of the property. Town centre is 15-20 mins walk Mainline station is 25 mins walk

Top guest favourite
A wooden cabin nestled within lush greenery is framed by vibrant purple flowers. The cabin features a welcoming patio area, surrounded by various shrubs and trees, creating a peaceful woodland atmosphere.
Cabin
5 out of 5 average rating, 274 reviews

Woodland Lodge 7 min walk to tube/station

Nestled at the foot of a beautiful woodland garden, The Lodge is clearly separated from the main house. Tucked away in its own peaceful wooded setting, the property offers a rare blend of tranquillity and convenience. Just a short walk from the village and only 7 minutes from the station, with fast trains reaching central London in 30 minutes. Whether you're visiting for work or leisure, this self-contained cabin provides a tranquil base with modern comforts and beautiful natural surroundings.

Guest favourite
An inviting wooden lodge interior is highlighted by a spacious bed adorned with plush pillows. A small dining table and chairs are positioned nearby, with large windows allowing natural light to fill the room. The angled ceiling and warm wood finish create a cozy atmosphere.
Place to stay
4.95 out of 5 average rating, 116 reviews

Stag Lodges

Nestled amongst the stunning views of the Chess Valley, Stag Lodges welcomes you to experience glamping in the beautiful Hertfordshire countryside with all the comforts of your own home but in a luxury, handcrafted wooden lodge. Chorleywood is on the Met Line, allowing a short journey into London. We are also on the doorstep of Warner Bros Studio Tour and other famous attractions. Whether its a special occasion for two, planning a family adventure or time with friends, Stag Lodges is for you!

Guest favourite
The exterior of the studio is displayed during a sunset, with a warm pink sky glowing above. A conservatory with large windows is visible, surrounded by a lush garden featuring blooming flowers and green grass. The countryside backdrop includes distant trees and open fields.
Farm stay
4.85 out of 5 average rating, 163 reviews

Stunning spacious Riverside House in the Chilterns

Stunning Riverside house with modern & spacious living. River Chess flows outside the king size bedroom with wonderful views of the countryside beyond. The property includes wet room, kitchen, huge sitting/dining room (double sofa bed) fibre broadband & beautiful conservatory with views to a second river. There is private access to the Chess Valley walk. Nearby Amersham, Chesham & Chalfont Underground take you to London in 30 mins. Harry Potter World is 15min away. Heathrow is 25 mins away

Top guest favourite
A charming cottage is set in a green landscape, featuring a sloped roof and dark exterior walls. The front porch is accessible by steps and showcases a small seating area with a table and chairs. Large windows allow natural light to brighten the entrance.
Barn
4.98 out of 5 average rating, 381 reviews

The Stables in Historic Berkhamsted

Welcome to one of the most historic parts of Berkhamsted - the hilltop site of Old Berkhamsted Place, and the original Grade 2* listed barn which remains, reputedly, the largest medieval barn in the counties of Beds, Bucks & Herts. The Stables is a spotlessly chic cottage for 2 with large gardens & parking, offering luxury linen & towels, wi-fi & TV. Ideal town/country position - 10mins walk to town centre with cafes, restos, boutiques and antique stores, and train to London is only 35mins!

Top guest favourite
A serene scene showcases a cottage surrounded by lush greenery and a private lake. Two swans glide across the calm water, while the cottage, with its wooden facade and sloped roof, is nestled among the trees, offering a peaceful retreat in nature.
Cottage
5 out of 5 average rating, 252 reviews

Crestyl Cottage riverside barn for 2 with hot tub

Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.

Top guest favourite
A detached house with a brick and stucco exterior is visible. A paved driveway accommodates two vehicles, including a dark sedan and a blue SUV. Landscaping features a short hedge and a gravel area, framed by blue skies and a few scattered clouds.
Guest house
4.98 out of 5 average rating, 146 reviews

Self-contained studio Wokingham

A self-contained newly build 20 m2 studio with separate entrance and parking. The studio is comprised of an en-suite bathroom, a super-king bed, a tall boy and a work desk. A kitchenette just next to the room with fridge freezer, microwave, kettle, toaster, coffee machine, washing machine and a tumble dryer. “The kitchenette doesn’t have a stove or an oven.” The studio is brand new and built to high standards. The studio is a 15 minutes walk to Wokingham train station and town centre.

Top guest favourite
The entrance of the studio apartment features a charming brick façade adorned with vibrant flowers. A small wooden bench sits on a stone patio, flanked by decorative planters filled with blossoms. A white front door with glass panels invites guests into the cozy space.
Guest suite
4.99 out of 5 average rating, 121 reviews

Renearth - Private, modern double bed studio apt.

Our ground floor studio apartment is conveniently located to Amersham town centre with easy access to London via the Metropolitan and Chiltern lines. The apartment is attached to our house with its own private entrance. It consists of a fully fitted kitchen, spacious bathroom, comfortable, cosy bedroom and its own secluded patio. Located in a quiet Close, with footpath access to Amersham town centre with numerous shops and restaurants. Close by is the historic town of Old Amersham.

Top guest favourite
The exterior of the lodge is shown, featuring wooden walls and a slate roof. A private courtyard is visible, bordered by greenery and a stone-paved area. Large windows allow natural light to enter the lodge, creating an inviting atmosphere.
Tiny home
4.98 out of 5 average rating, 199 reviews

The Stable Lodge

The Lodge is light, airy and modern, whilst providing original character and features. An ideal romantic getaway for couples, those visiting family and friends, or somewhere to base yourself for a weekend of walking in the chilterns; this cosy, self-contained lodge is perfect for those looking to get away from it all. Set on a working stable yard surrounded by private ancient woodland accessible to guests. Private fenced garden, however not secure on one side for a determined dog.

Top guest favourite
The living area is designed with a corner sofa, accented by cushions. A flat-screen TV is positioned against the wall and a small coffee table sits on a round rug. Light enters through double windows with shutters, and a gas stove is showcased beneath the mantel.
Home
4.98 out of 5 average rating, 288 reviews

Cosy Victorian cottage in central Berkhamsted

Renovated beautiful cottage with open plan living on the ground floor with corner sofa and gas stove. French doors are leading out to a private courtyard garden. Well appointed kitchen with hob, oven and dishwasher. Washing machine in separate lobby leading through to a ground floor shower room / WC. Upstairs there are 2 bedrooms , a main bedroom with king-size bed and a twin room with 2 single beds. Self check in

Popular amenities for Chiltern family-friendly rentals

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Quick stats about holiday rentals that are family-friendly in Chiltern

  • Total holiday rentals

    Explore 200 holiday rentals in Chiltern

  • Nightly prices starting at

    Chiltern holiday rentals start at £23 per night before taxes and fees

  • Verified guest reviews

    Over 5,780 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    190 of Chiltern holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chiltern rentals

  • 4.8 Average rating

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