
Vacation rentals in Penn
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Penn
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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

1 bed apartment. Village location. Heathrow 25mins
This one bedroom apartment is annexed within our family home but benefits from its own entrance and facilities. Quiet village location but easy access to transport links (Heathrow is 20 mins drive, London 35 mins on the train). We are on the edge of the Chilterns, an UNESCO recognised Area of Outstanding Natural Beauty. We are taking bookings using the Covid19 guidelines and legislation set out on the UK government website. If the road map changes then availability may also need to change.

Riverside Boathouse
A warm and cosy studio style converted boat house on the edge of the River Thames in Cookham, Berkshire. Separate from the main house, the double glazed studio boathouse with en-suite, decorated beautifully. Egyptian cotton linen and nice towels. Relax with views of the river. Blackout blinds, kitchen, en-suite shower room, fridge, double glazing, heating, TV, WIFI, laptop area, outdoor seating/picnic blanket, umbrellas, off road parking, boat mooring, EV Charging Point (fee applies).

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.

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 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.

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.

Marlow F3 A Lovely 1-bed apartment- WiFi & Parking
Stunning 1 bedroom apartment in a great central location in Marlow. Free on-site parking and private patio garden with sofas and dining. Please Read the Reviews. Brand new kitchen, with all appliances, coffee machine. Free high-speed WIFI. TV's in the living room and bedroom, with fire sticks. Dedicated fitness area with spinning bike, weights and TRX cables. Additional bed charged at £35.00. (This is a foldout chair bed suitable for a child up to 12 years)

Luxury 2 bedroom cottage
Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

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 vacation rentals
Other great vacation rentals in Penn

Free Parking Modern Cosy Flat, M40 Access

Warm, spacious loft room in Cookham

Beaconsfield Yew Tree

Best located : 1 bed apartment in Buckinghamshire

Pretty home in woods near Marlow and High Wycombe

Idyllic retreat - 2 bed, 1 bath

Flat Beaconsfield Bucks UK patio & free parking

Splendid private access annex Beaconsfield
Quick stats about vacation rentals in Penn
Total rentals
70 properties
Nightly prices starting at
R695 ZAR before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Frequently Asked Questions
Do apartment rentals in Penn have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Penn. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Penn?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Penn have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Penn. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Penn?
Penn has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Penn?
Yes! Work meets play with ease at over 20 vacation rentals in Penn featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Penn?
Experience the best of Penn with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Penn have free parking?
Absolutely! We offer over 20 house rentals with free parking in Penn. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Penn?
Make yourself at home in Penn by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in Winchmore Hill, over 120 vacation rentals in Knotty Green, and over 260 vacation rentals in Penn.
Destinations to explore
- Paris Vacation rentals
- London Vacation rentals
- Amsterdam Vacation rentals
- Picardy Vacation rentals
- Grand Paris Vacation rentals
- River Thames Vacation rentals
- South West England Vacation rentals
- Inner London Vacation rentals
- Dublin Vacation rentals
- Rivière Vacation rentals
- Brussels Vacation rentals
- South London Vacation rentals
- British Museum
- Covent Garden
- Buckingham Palace
- Wembley Stadium
- Big Ben
- Trafalgar Square
- Tower Bridge
- London Bridge
- Hampstead Heath
- The O2
- Harrods
- Barbican Centre
- St. Paul's Cathedral
- Emirates Stadium
- ExCeL London
- St Pancras International
- Camden Market
- London Stadium
- Alexandra Palace
- Oxford University
- Clapham Common
- Blenheim Palace
- Silverstone Circuit
- Primrose Hill