Family-friendly vacation 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 favorite

Barn in Warfield

4.91 out of 5 average rating, 778 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 favorite

Guest suite in Amersham

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

Guesthouse in Bennett End

4.87 out of 5 average rating, 427 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 favorite

Bungalow in Watford

4.86 out of 5 average rating, 242 reviews

Attractive house in Watford

Located in a quiet residential road a few minutes from London. Modern well equipped kitchen and bathroom. The well presented garden has a patio area with a barbeque. Close to the Warner Bros Harry Potter Studio Tour, local restaurants, bars, historic sites, nature reserves, golfing, boating as well as Watford Town Football Club. Average journey into London by train only 20 minutes from Watford Junction or 20 minutes by car. Very convenient for events at the Grove and Wembley Stadium and Arena.

Guest favorite

Home in Buckinghamshire

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 favorite

Cottage in Englefield Green

5 out of 5 average rating, 310 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

Rental unit in Slough

4.82 out of 5 average rating, 238 reviews

Lovely Slough Home Near Heathrow & Windsor

New refreshed and decor, ideal for Work, Business or holidays. Heathrow Airport 8 Miles (10-15 Minutes), M4 Junction-5 is 2 Miles, Windsor 3.5 Miles (5-10 Minutes), Legoland 4 Miles (8 Minutes), Central London 20 Miles (30-40 Minutes), Reading 20 Miles (20-30 Minutes) and Oxford 38 Miles (1 Hrs.) Supermarket Asda 1.5 Miles Approximately. Please note: Due to COVID - 19, we’re taking extra steps to clean and sanitize frequently touched surfaces between reservations.

Superhost

Guesthouse in Buckinghamshire

4.88 out of 5 average rating, 140 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 favorite

Barn in Kingsey

4.93 out of 5 average rating, 438 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 favorite

Rental unit in Cookham

4.94 out of 5 average rating, 582 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 favorite

Townhouse in Buckinghamshire

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 favorite

Bungalow in Tutts Clump

4.96 out of 5 average rating, 266 reviews

Garden Cottage..pretty countryside location

Our cottage is in a great little hamlet in Berkshire and is the perfect location for walking and exploring the countryside and the towns of Newbury and Reading.The cottage itself is open plan and is very light and airy with a modern mediterranean feel to it. It has two lovely bedrooms and two bathrooms. It is located in an area of outstanding natural beauty and is perfect for a quiet getaway or a busy shopping spree!