
Holiday rentals in Penn
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Quick stats about holiday rentals in Penn

Total holiday rentals
Explore 80 holiday rentals in Penn

Nightly prices starting at
Penn holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 1,750 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
70 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
Top-rated holiday rentals in Penn
Guests agree: these stays are highly rated for location, cleanliness and more.

Stunning One Bedroom Annex
The annex is very cosy with free parking on front drive for one guest car. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table & gazebo area at the bottom ideal for smokers. Our house has the 'Loudwater' sign 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.

Stylish Character Home | Old Amersham Market Town
In the heart of the historic market town of Old Amersham, dating back to 1580 is the boutique, recently (2021) renovated and period Hops Cottage (given its name from the old hop house and brewery next door). The flat is on the first floor with large vaulted living area with mezzanine, full of light with windows on two sides and in the roof. The property still retains period features including original oak beams. Converted with luxury and comfort in mind, its makes for a memorable stay.

The Woodland Retreat With Private Hot Tub Spa
Our brand new listing is a truly unique woodland retreat with a luxury super king bed, dedicated private hot tub & 65 inch tv. Perfect for a couple get-away, this place will take your breath away. Nestled in our remote private woodland on our farm estate this little gem is in touch with nature yet fully fitted with all the home comforts you need. Additionally the woodland retreat includes: 1x private bathroom, a fully fitted outdoor kitchen, WiFi and a bespoke oak outdoor dining table.

Beautiful English Cottage
A unique, luxury, 5 bedroom, English cottage, in the Chilterns. Walking distance to town/train/shops/pub and 30 mins by train into London. Open plan downstairs living with huge open fireplace and a chefs dream kitchen. All rooms ensuite, with Egyptian cotton sheets and fluffy towels. Beautiful enclosed gardens, with BBQ hut and pretty summer house, and huge outside table, complete with cushions, perfect for dining. Herb garden and fruit trees to the rear. Large front drive for parking.

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.

Hagrid Hut Themed - Hot Tub - Warner Bro Studio
Hagrid & Fang are away and would like you to watch over his home, located next to the Forbidden Forest! This unique Glamping experience is conveniently located only 12 minuets drive from the Warner bros Studio Tour & 40 minuets to central London via Chorleywood Metropolitan line. Hagrid's Hut sleeps five wizards - making it the perfect accommodation choice for families and friends. Soak under the stars in the leaky cauldron wood fired hot tub nestled in nature, MAGIC.

The Crafty Fox Chalfont
Step into a beautifully restored 16th-century coach house in the heart of Chalfont St Giles High Street. Bursting with character, this unique retreat features exposed wooden beams, luxury designer décor, and a private hot tub for relaxing after a day of exploring. Cleverly designed to maximise space, the cosy yet stylish interior comfortably sleeps up to 4 guests. Enjoy historic charm, modern comforts, and an unbeatable village-centre location right on your doorstep.

Escape From The City
Escape the city and unwind in this cozy, stylish home tucked away in a quiet part of High Wycombe. Just minutes from the stunning Chiltern Hills, it's the perfect base for countryside walks, pub lunches, and total relaxation. 2 comfy bedrooms + Sofa Bed Free parking Fast Wi-Fi + Smart TV Serene Private garden Enjoy fresh air, peaceful mornings, and beautiful local trails – all just a short hop from the city. Your relaxing countryside escape starts here

The Hayloft, Downley Common
The Hayloft is situated at Downley Farmhouse in Downley, Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames. Downley is a small village set around a common with a friendly local pub, The Le De Spencer Arms, which serves good food. The village has all the necessary local amenities and is within easy reach of all major communication networks and local attractions.

Cosy 1 bed rural cottage - Orchard/Vineyard view
A charming 1 bed rural cottage retreat set within a 16 acre estate and working farm near London, M25/M40. Self-contained cottage with kitchen, lounge and bathroom. Large main bedroom with comfortable super-king bed, ample clothes storage and dressing table. Extra sofa-bed, z-bed and travel cot available if needed. Private courtyard garden access. The adjoining 6 bed farmhouse is also available to rent.

Detached Studio
Detached studio is located in Loudwater, just off Junction 3 of the M40, offering easy access by car or local transport links. Free on-street parking. - Clean and comfortable living space. - TV with Netflix - Chromecast - Kitchenette - Double Bed - Suitable for single or couple. - Shower Room - towels, hand soap and shower gel provided. - Electric heating throughout.

Charming 3-Bed Private Cottage in the Chilterns
Peaceful, private 3-bed cottage on Nightingales Lane in the Chiltern Hills. Fully self-contained with parking, garden seating, modern kitchen, cosy living room and two bathrooms. Perfect for families, walkers and countryside breaks. Minutes from Chalfont & Latimer Station with fast links to London. Close to Amersham, Gerrards Cross and local pubs, shops and scenic trails.
Popular amenities for Penn holiday rentals
Other great holiday rentals in Penn

Comfortable & Tranquil Newly Renovated Apartment

High Wycombe Centre- 2 bed flat

Flat 4 Beaconsfield Town Easy walk to NFTS & Train

Serene & Private Annexe in Village Centre

The Wild Bloom- 3 bed with parking

Home from Home comfort and convenience.

A tranquil, self-contained guest house in Cookham

Charming Country Cottage with Lovely Views
When is the best time to visit Penn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £80 | £89 | £92 | £115 | £78 | £75 | £100 | £100 | £69 | £67 | £85 | £84 |
| Avg. temp | 5°C | 5°C | 8°C | 10°C | 13°C | 16°C | 18°C | 18°C | 15°C | 12°C | 8°C | 5°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Penn?
Penn has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Penn?
Experience the best of Penn with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Penn?
Four-legged friends are welcome in Penn. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there house rentals with a dedicated workspace in Penn?
Yes! Work meets play with ease at over 10 house rentals in Penn featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Penn have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Penn. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Penn have wifi?
Absolutely! We offer over 30 house rentals with wifi in Penn. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Penn have free parking?
Absolutely! We offer over 10 apartment rentals with free parking 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 free parking, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- The O2
- ExCeL London
- Emirates Stadium
- Tower Bridge
- Silverstone Circuit
- Clapham Common
- University of Oxford
- Buckingham Palace
- Thorpe Park Resort
- Blenheim Palace
- Chessington World of Adventures Resort
- South Downs National Park
- Alexandra Palace
- London Stadium
- Big Ben
- Windsor Castle
- Victoria Park





