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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Guest favourite

Barn

4.91 out of 5 average rating, 783 reviews

Delightful small converted barn

Unique newly converted small barn, bright, light and self contained. Sleeps 3 adults or 2 adults and 2 children (or 2 small adults) due to restricted height space in loft. Large gravel drive behind big, wooden gates for safe and easy parking. An assortment of Teas, coffee & biscuits. Breakfast is not provided. Situated down a country lane, within the garden of the house, walking distance to pubs and restaurants. A few miles from Legoland, Ascot, Windsor, Train stations to London and Reading.

Guest favourite

Guest suite

4.96 out of 5 average rating, 328 reviews

Peaceful, self-contained apartment on two levels

Overlooking private garden, situated in historic old town of Amersham, the apartment, once lived in by Roald Dahl, is close to restaurants, pubs, coffee shops plus fashion boutiques. Own entrance, fitted kitchen with electric hob, oven, microwave, fridge, washing machine. Also sitting room with sofa-bed, TV & DVD player, double bedroom with TV, bathroom with bath and separate shower unit. Full central heating, free Wi-Fi. Secluded outside seating area. Unlimited free parking in High Street.

Superhost

Guest house

4.87 out of 5 average rating, 429 reviews

Mary's Cabin

Completely peaceful, with fantastic views-totally isolated with its own private entrance. Set in the Chiltern hills- Mary’s Cabin is 2minutes stroll from the Restaurant of the Year- In an Area of Outstanding Natural Beauty;-walking, road & mountain biking- pub 7minutes up through the woods- 35mins from Heathrow and Oxford -Central London-50mins . Couples, solo adventurers, and small families (with 1small child). Sadly, since the advent of Covid, we no longer provide breakfast for our guests

Guest favourite

Place to stay

4.96 out of 5 average rating, 266 reviews

Cottage/Annex. B&B available

One large bedroom cottage with bathroom. Part of a 19th Century farmhouse set in 1 1/2 acre gardens. Mainline station/tube 25 mins walk & 4mins drive. 25 mins to London. 10 min to Pinewood & 15 to Leavesden. Convenient for Heathrow/Luton. Perfect to explore the Chilterns/Grand Union canal/the Harry Potter Experience. Egyptian cotton sheets, fluffy gowns, SMART TV, tea/coffee making facilities. Fridge and microwave on request. Room for 2 Adults and 1 small child or baby. Breakfast on request.

Guest favourite

Home

4.9 out of 5 average rating, 157 reviews

The Stables, Little Marlow

A fabulous, converted barn, located in the very desirable village of Little Marlow, Bucks. The property is set within 3/4 acre for your private use and has it's own private driveway + parking. The interior has underfloor heating, a wood burning stove, panelled walls, en-suite bathroom and a family bathroom. Little Marlow has been in numerous Midsomer Murder TV series. The village has two pubs, a cricket ground and a church. The property is a 10 min walk to the river Thames. AONB & cons. area

Guest favourite

Cottage

4.88 out of 5 average rating, 111 reviews

Elegant Countryside Cottage near Oxford

Spacious and beautifully finished countryside cottage in the heart of Brill village with views across the village green and just a 2 min walk from The Pointer pub. The perfect base for exploring the countryside, Oxford, Thame and Bicester Village. Blenheim Palace, Waddesdon Manor, the Cotswolds, Silverstone race track and London are all within easy reach. Well behaved dogs over 2 years old welcome! * Host My House manages this property which is owned by Christopher & Gillian Scott-Mackirdy *

Guest favourite

Cottage

5 out of 5 average rating, 314 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

Superhost

Guest house

4.88 out of 5 average rating, 141 reviews

The Old Hay Barn, Ashley Green

Our rustic Victorian barn in located in the heart of Ashley Green village, a short drive to both historical Berkhamsted or Chesham high streets and train stations. Delightfully converted to a charming, private one-bedroom residence, it is fully furnished to a high standard. The barn has access to its own private garden and parking space. Its warm and authentic feel makes it ideal for a getaway, mini country break or a relaxing space during the working week.

Guest favourite

Barn

4.93 out of 5 average rating, 441 reviews

Self-contained barn conversion

The Farrow is a pretty self-contained annex within the grounds of Nettlebed Barn. Set in tranquil surroundings on the edge of the 12th century hamlet of Kingsey. It has the additional benefit of stunning picturesque views of rolling fields framed by the beautiful vista of the Chiltern hills. Just a 5 minute drive to Haddenham train station will give you access to central London in 40 minutes and the beautiful and historic city of Oxford in just 29 mins.

Guest favourite

Rental unit

4.94 out of 5 average rating, 584 reviews

Old Butchers Wine Cellar 15th Century Apartment

Our restored 15th century apartment is in a unique position on Cookham High Street, located within 500 meters to 7 different restaurants and pubs and four Michelin Star restaurants within 3 miles. Situated above our beautiful wine shop with a pop up wine bar on Thursday, Friday and Saturday nights. We have very comfortable beds, 100% cotton sheets and towels. The perfect choice for couples, business travellers and families.

Guest favourite

Townhouse

4.97 out of 5 average rating, 151 reviews

Princes Risborough, 3 Double Bedrooms, Big Garden

This is our lovely end-terraced Edwardian house where you can enjoy country walks in the Chilterns, go for bike rides, or have a BBQ in the beautiful garden. The house is just a short walk from the train station in the medieval market town of Princes Risborough. We have private parking for one car and bicycles are available for the guests to use. The house is ideal for max 4 grown-ups, your pet can be brought on request.

Guest favourite

Home

4.95 out of 5 average rating, 304 reviews

The Olde Dairy renovated barn

The Olde Dairy is a newly renovated barn which is very spacious and has a very cosy ambience. Popular with visitors to Warner Brothers Studios ‘ Harry Potter’ Bekonscot model village, Roald Dahl museum, Chiltern Open Air museum, Bovingdon Studios, Legoland, Windsor, and the train station 5 mins away straight into London Baker Street approximately 40mins, there are many lovely local pubs and walks on our doorstep.