Family-friendly holiday rentals in Penn

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Penn

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

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Superhost
The outdoor dining area features a table with four chairs under a green umbrella. Potted plants frame the space, and the background showcases large glass doors leading into the bungalow. Bright greenery and clear skies enhance the comfortable setting.
Bungalow
4.85 out of 5 average rating, 246 reviews

Stunning Chiltern Views from Old Amersham Bungalow

NEW BUNGALOW Kyteway is a self-contained detached studio between the historic town of Old Amersham and the rolling Chiltern Hills. Offering fully equipped kitchen, spacious shower room, double bed in sleeping area, dining table, storage, and sofa bed. BEAUTIFUL VIEWS from private dining patio & separate sun terrace. Short walk to historic old town and easy access to new town (inc station to London) on foot, by car, or local bus. Adjacent to countryside footpaths. Unrestricted on-street parking.

Top guest favourite
An open plan living area is showcased with a dark sofa, light wooden coffee table, and a small round dining table. A floral wall hanging is displayed above the sofa, while natural light enters through a skylight, illuminating the neutral-colored walls.
Guest suite
4.98 out of 5 average rating, 136 reviews

Bright self-contained annexe with its own garden

This recently renovated, self-contained, quiet and bright annexe has everything you need for a relaxing stay in the Chilterns. It offers own entrance, open plan living area with a kitchen and a small table, bathroom and a bedroom with a king sized bed. Enjoy your morning coffee or a picnic in the sunshine in your own little garden with table and comfortable chairs. Conveniently located, only 8 min walk to Amersham station and 1 min walk to the high street with many cafes, shops and restaurants.

Guest favourite
Cabin
4.94 out of 5 average rating, 103 reviews

Sleep in the Trees - Hot Tub, Sauna and Slide

The Owls treehouse is a fun filled family unit with a fantastic slide including a hot tub and sauna. With unusual tunnel shaped rooms looking out to beautiful woodland country side, this unique getaway is exciting to share with loved ones. Attractions include Harry Potter studios, 35min Trains to London, Legoland Windsor to name a few. Also Featured on 'Amazing small spaces' and 'This Moring' Why not book out of the ordinary and stay with us, we look forward to your stay at North Hill Farm

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
4.96 out of 5 average rating, 148 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!

Superhost
A serene bedroom features vaulted ceilings with exposed beams and a large window offering views of greenery. The ornate bed is adorned with soft linens and decorative pillows. A vintage dresser with intricate details complements the space alongside a delicate chandelier.
Loft
4.79 out of 5 average rating, 171 reviews

Luxury Apartment, The Barn, Cookham

The Barn is tucked away in a private courtyard set back on a picturesque and quiet lane that leads towards the village high street. Steeped in history and oozing character, it dates back to the 18th century. Vaulted ceilings and old beams frame the bedrooms which are furnished with an ornate bed/sofa bed/Egyptian cotton bed linen in a combination of dusky pinks/greys all in a shabby chic style. Chandeliers, silk bedspread, Farrow & Ball paint and Bamford Botanical sustainably made toiletries.

Top guest favourite
Guest suite
4.95 out of 5 average rating, 356 reviews

Charming 1 bedroom place with parking.

Relax in the Chilterns in a comfortable self contained suite with En-suite shower, dining area, 42" Smart TV, fridge and microwave. Pub 15 minute stroll away. Nearby towns of Chesham & Amersham have transport links into London and offer a host of restaurants and shops. The Chilterns AONB is well renowned among walkers. We are convenient for The Harry Potter studios (20 min drive) The property is self contained and totally separate from the owner's house so you can come and go as you please.

Top guest favourite
The exterior of Chiltern Barn is depicted, showcasing a two-story building with a slate roof and natural stone façade. Large glass doors open onto a stone patio area, and a cobbled courtyard is visible in front, framed by lush greenery and a clear blue sky.
Cottage
4.97 out of 5 average rating, 364 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

Chiltern Barn is a 230 year old converted hay barn in Wheeler End in Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames with easy access to the M40. Wheeler End is a small village in The Chilterns built around a large common. There is a friendly local pub, The Chequers and Lane End, less than mile away has local amenities, including a well stocked Londis, a newsagents, excellent farm shop, gastro-pub, Indian and Chinese takeaways, hair dressers etc.

Guest favourite
An airy living space is highlighted by high ceilings and natural light streaming through large windows. A mix of seating options, including a gray sofa and a white armchair, surrounds a coffee table. A dining area with white chairs complements a gray sideboard.
Cottage
4.97 out of 5 average rating, 167 reviews

Delightful, rural, modern cottage, large garden.

Spectacular , quiet, rural cottage. This cottage contains a large maisonette room with a super-king bed and a downstairs room with two double beds, ideal for up to 4 children who can share or two adults who prefer double beds. The bathroom has a bath with a shower in it. There is a fully operating kitchen/dining room. Lots of walks nearby either to the pubs in Little Missenden, Penn woods and Penn Street or further into Old Amersham. Shared use of a large garden and tennis court.

Top guest favourite
A dining area is set outside with a glass-top table surrounded by four wicker chairs. The exterior of the building is textured, featuring a black front door and a window with white trim, complemented by a small shrub nearby.
Guest house
4.94 out of 5 average rating, 155 reviews

Stunning One Bedroom Annex

The annex is very cosy with free parking on front drive. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table and gazebo area at the bottom ideal for smokers. Our house has the 'Loudwater' sign right outside our house if you don't see the number 9 in the dark. We are also directly opposite Thanestead Court. Our place is just off junction 3 High Wycombe East from M40 so a great location to get to locations.

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
4.97 out of 5 average rating, 257 reviews

The Stable Lodge

The Lodge is light, airy and modern, whilst providing original character and features. An ideal 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
A cozy corner of the apartment features a decorative fireplace with an ornate mantle. Handwritten notes are displayed above the mantle, and a wooden desk is positioned nearby. A vintage chair and a chandelier add to the room's charm, with warm light filtering through a window.
Apartment
4.97 out of 5 average rating, 192 reviews

Wizards Retreat - 8 Mins to HP Warner Bros Studio!

Welcome to ‘The Wizard’s Retreat’ This Airbnb is perfectly located just an 8-minute drive from Warner Bros. Studios, making it the ideal stay for fans visiting the Harry Potter Tour. There's wizard books to read, games to play & spooky potions to see! Whether it’s a spellbinding weekend with friends, a cosy couple’s getaway, or a family adventure, The Wizard’s Retreat has been designed to capture the wonder and excitement of the wizarding world for all to enjoy!

Guest favourite
A detached barn-style maisonette with a combination of brick and stone exterior stands in a landscaped setting. Large windows allow natural light to filter through, while a staircase leads to an upper terrace. Well-maintained lawns provide a green backdrop.
Cottage
4.94 out of 5 average rating, 201 reviews

Luxurious Barn between Marlow & Henley

A luxurious 2 bedroom detached maisonette barn with garden, terrace and outstanding views over the Chiltern Hills.Situated in the picturesque village of Medemenham, 2 miles from Marlow and 5 miles from Henley-on-Thames. Located opposite Danesfield House Hotel and with stunning woodland walks accessible straight from the property and easy access to the River and Harleyford Golf Course . The property has 2 parking spaces, air conditioning ,wifi .

Popular amenities for Penn family-friendly rentals

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

  • Total holiday rentals

    Explore 30 holiday rentals in Penn

  • Nightly prices starting at

    Penn holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Penn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Penn rentals

  • 4.7 Average rating

    Penn stays receive an average rating of 4.7 out of 5 from guests