
Family-friendly holiday rentals in Penn
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Top-rated family-friendly rentals in Penn
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

The Nook at Pine View - set in Roald Dahl Country
The Nook at Pine View, is set within the Chiltern Hills in a designated Area of Outstanding Natural Beauty. In the heart of "Roald Dahl Country", Cobblers Hill is famously written within the pages of "Danny Champion of the World". The Nook benefits from stunning rural views and the peace & quiet of country living but with easy access to award-winning restaurants, pubs & cafes all just a short drive. A 45 min train to London. The surrounding area has some renowned country walks and cycle paths.

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.

Stunning spacious riverside house in the Chilterns
Unique opportunity to stay in the heart of the stunning Chilterns with modern & spacious living. The River Chess flows past the bed with wonderful views of countryside beyond. Property offers large sitting/dining room (dbl sofa bed), wet room, kitchen & conservatory. Fibre broadband. Glorious walking on the Chess Valley Walk. Nearby Amersham, Chalfont & Chenies offer superb restaurants/shops and the Metropolitan line tube to central London (30 mins). Harry Potter World 15min, Heathrow 25min away

Apartment 24 GERRARDS CROSS
Delightful fully self-contained luxury one double bed apartment with own private entrance (your host is an interior designer). 10 minute level walk to Gerrards Cross village with a vast variety of restaurants, supermarkets and shops. Located 25 minutes from London Marylebone by use of Chiltern Railway Services at Gerrards Cross Station (10-15 minute walk from property) and no more than 40 minute drive from London Heathrow. This accommodation will provide a home away from home experience.

Charming 1 bedroom place with parking.
Relax in the beautiful Chilterns in a comfortable self contained suite with En-suite shower, dining area, 40" Smart TV, fridge. 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.

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.

Home from Home in Hertfordshire & 1 FREE parking
Cosy self-contained annex attached to house with its own lounge, kitchen and bedroom. Shared porch. Free on-site parking and a private patio make relaxing easy. Quick 5-min drive to Hemel Hempstead station, business parks, bars & restaurants. A short uphill walk from Apsley station. Check out my guide book for Harry Potter World, ski centre and more places to visit! * Wi-Fi & workspace * Fully equipped kitchen * Self check-in * Adults only * No smoking Please check location!

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.

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.

Stunning One Bedroom Annex
The annex is very cosy. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table. 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 all places in Buckinghamshire as well as to London. The location is very peaceful.

18th century cottage
Self contained character annex in the beautiful Buckinghamshire countryside. Low ceilings and a narrow steep staircase with handrail and stair gates top and bottom. Parking spaces at the front and use of the pretty garden to the rear. Fantastic location on the edge of the Chilterns; good road and rail links to London and Oxford, close to the Thames, Windsor, Marlow, Cliveden, Hedsor House, Harry Potter Studios and Legoland. Plus there’s a pub next door!

Budget Bliss in High Wycombe
A unit on its own, away from the main residence, this is a modern, comfortable annexe with a high-end finish. Ideal for people working in the area, short stops or longer stays. Even for those looking for long country walks and a home away from home for some peace and quiet downtime. Ensuite with a double bed, kitchenette with 2 burner hob, fridge freezer, microwave and lots of storage with a separate built in wardrobe. Sleeps 2 comfortably.
Popular amenities for Penn family-friendly rentals
Family-friendly home rentals with a hot tub

The Woodland Cabin with Private Hot Tub Spa

Luxury self-contained Annexe with balcony Jacuzzi

Luxury retreat with extensive leisure facilities

Hilly Hideaway, Hot Tub Countryside Retreat

Tree House - Hot Tub on balcony

White Cottage Annexe with riverside garden hot tub

Crestyl Cottage riverside barn for 2 with hot tub

Farm stay in Buckinghamshire
Family- and pet-friendly home rentals

Stunning country retreat or romantic mini break

Marlow F3 A Lovely 1-bed apartment- WiFi & Parking

Luxury Shepherd's Hut with stunning sunset views!

The Stables in Historic Berkhamsted

Fantastic s/c barn in "secret" Chiltern valley

Tiles Farm Studio - Heart of the Chilterns

The Old Music Studio - retreat with tennis court

The Stables
Family-friendly home rentals with a pool

The Pool House

Luxury Battersea studio w open fire, close to Park

Spacious Sunny Apartment

Bell Tent Glamping Single unit, self contained.

The Coach House

Two Bed Large Countryside Barn with Indoor Pool

Escape to Country Living at its Finest!

The Luxury Cottage – Surrey Countryside Retreat
Quick stats about holiday rentals that are family-friendly in Penn

Total holiday rentals
Explore 20 holiday rentals in Penn

Nightly prices starting at
Penn holiday rentals start at $67 NZD per night before taxes and fees

Verified guest reviews
Over 540 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Penn holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Penn rentals

4.7 Average rating
Penn stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Tower Bridge
- Big Ben
- Paddington
- British Museum
- Natural History Museum
- Covent Garden
- London Bridge
- Marble Arch
- Tottenham Court Road
- Buckingham Palace
- Hampstead Heath
- Kings Cross
- St Pancras International
- The O2
- Piccadilly Theatre
- Trafalgar Square
- Battersea Power Station (disused)
- Emirates Stadium
- ExCeL London
- Wembley Stadium
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market




