
Holiday rentals in Penn
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Penn

Total holiday rentals
Explore 70 holiday rentals in Penn

Nightly prices starting at
Penn holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 1,600 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
60 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.

Comfortable & Tranquil Newly Renovated Apartment
Stylish & Cosy two-bedroomed ground floor property. Features a stunning open plan Kitchen/Lounge/Diner and modern bathroom. Combi boiler & Hive controlled heating. Set in a quiet location within easy walking distance of High Wycombe town centre. 5 mins walk to a beautiful local park. 5 mins walk to a Superstore with Starbucks and Wenzels. Apartment has private parking. Excellent rail links to London. 30 mins travel time from High Wycombe train station. Relax in this calm & welcoming space.

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.

Flat 2 Beaconsfield Town Easy walk to NFTS & Train
Warwick Road Studios are new furnished, self-catering modern apartments. Just a 2 minute walk to train station and 22 minutes to London Marylebone, it stops at Wembley Stadium/Arena. Professionally cleaned. Designed to give you more space and facilities than a hotel room plus Superfast WiFi. Situated in Beaconsfield New Town, with many restaurants, shops and bars. Set in the Chiltern Hills with spectacular countryside. Only a short walk to The National Film and Television School NFTS. Lovely.

17th Century Barn in quiet country village
A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

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.

Home from Home comfort and convenience.
Number 2 Hartley Court is one of 5 houses which make up the historic, Grade 2 listed, 1874 Pilgrims House with its unique chimneys and beautiful features. We are in the heart of Gerrards Cross between two commons with playground and woods. All amenities of the village, Restaurants, Tesco’s, railway station, Waitrose etc are a few minutes walk from us. Accommodation is all on one level with a delightful private garden and summerhouse. Guest off road parking available for 1 small car.

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.

Luxury cottage 5 mins walk from Marlow High St
Beautiful one bedroom cottage just a short walk from Marlow town centre and its award-winning restaurants. Full of character with a large kitchen, lounge and bedroom that blend seamlessly with tasteful furnishings. From the moment you step through the door, you’ll feel the warmth and character of this much-loved home. Perfect for enjoying countryside walks, and vibrant Marlow life. A bedroom, a bathroom and parking. It's located just 200m from the famous Hand & Flowers restaurant.

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.

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.

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.
Popular amenities for Penn holiday rentals
Other great holiday rentals in Penn

Stylish newly renovated Two bedroom apartment

Modern Country House

Deluxe 2 bed flat w/free parking

Serene & Private Annexe in Village Centre

Royal Grand Cottage: Pond + Wildlife + Nature

Stylish Character Home | Old Amersham Market Town

The Wild Bloom- 3 bed with parking

A tranquil, self-contained guest house in Cookham
When is the best time to visit Penn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $138 SGD | $154 SGD | $159 SGD | $199 SGD | $136 SGD | $131 SGD | $173 SGD | $173 SGD | $119 SGD | $116 SGD | $148 SGD | $146 SGD |
| 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 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.
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 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.
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.
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.
Do house rentals in Penn have free parking?
Absolutely! We offer over 30 house 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 a kitchen, over 10 homes with wifi, over 10 homes with free parking, 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
- ExCeL London
- The O2
- Emirates Stadium
- Tower Bridge
- Silverstone Circuit
- Clapham Common
- University of Oxford
- Buckingham Palace
- Blenheim Palace
- Thorpe Park Resort
- South Downs National Park
- Chessington World of Adventures Resort
- Alexandra Palace
- Big Ben
- London Stadium
- Windsor Castle
- Victoria Park





