Holiday rentals in Penn

Find and book unique accommodation on Airbnb

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 $39 SGD 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.

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Guest favourite
The exterior of the apartment building is featured, showcasing a three-story brick structure with a mix of white and brown finishes. Lush greenery surrounds the property, and a parked car occupies a designated parking space in the foreground.
Flat in High Wycombe
4.93 out of 5 average rating, 82 reviews

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.

Top guest favourite
The welcoming living area features a spacious gray sofa adorned with colorful cushions. A patterned area rug lies beneath the seating, which is accompanied by a stylish dining table. An open entryway leads to the kitchen, with abundant natural light streaming in from the garden.
Home in Marlow
5 out of 5 average rating, 140 reviews

Magical Marlow town centre

Wing Cottage is a charming period terraced cottage with log burner in the heart of Marlow. It has been stylishly refurbished and has its own secluded courtyard garden. 5 minutes walk from High St shops with Everyman Cinema, Tom Kerridge’s Michelin* Hand &Flowers & The Coach, plus Marlow Ivy Garden, Côte Brasserie, Piccolino, The Compleat Angler and several historic pubs. The Park and Thames Path river walk are 10 minutes walk. Nearby bus stops serve neighbouring Henley-on-Thames (8 miles away).

Guest favourite
A dining area is set outside with a glass-top table surrounded by four wicker chairs. The exterior of the building is textured, featuring a black front door and a window with white trim, complemented by a small shrub nearby.
Guest house in Loudwater
4.94 out of 5 average rating, 171 reviews

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.

Top guest favourite
Guest suite in Buckinghamshire
4.95 out of 5 average rating, 372 reviews

Charming 1 bedroom place with parking.

Relax in the Chilterns in a comfortable self contained suite with En-suite shower, dining area, 42" Smart TV, fridge and microwave. 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.

Guest favourite
A modern wooden cabin blends into its woodland surroundings, featuring large glass windows that offer views of the forest. An outdoor kitchen is visible beside a spacious dining table crafted from natural wood. Comfortable seating arrangements create a welcoming outdoor space.
Tiny home in Aylesbury
4.97 out of 5 average rating, 468 reviews

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.

Top guest favourite
The charming cottage features traditional brickwork and a steeply pitched roof. A well-maintained garden showcases vibrant lavender and lush green grass. Decorative flowering plants enhance the inviting entrance, framed by an archway of climbing greenery and detailed, patterned windows.
Cottage in Beaconsfield
5 out of 5 average rating, 20 reviews

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.

Top guest favourite
The exterior of the lodge is shown, featuring wooden walls and a slate roof. A private courtyard is visible, bordered by greenery and a stone-paved area. Large windows allow natural light to enter the lodge, creating an inviting atmosphere.
Tiny home in Holmer Green
4.97 out of 5 average rating, 270 reviews

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.

Guest favourite
Cabin in Chorleywood
4.96 out of 5 average rating, 116 reviews

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.

Superhost
Home in High Wycombe
4.78 out of 5 average rating, 32 reviews

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

Guest favourite
A stylish entryway features dark walls contrasted by wooden beams. A softly illuminated neon sign reading 'The Crafty Fox' is prominent, accompanied by a wall-mounted light fixture. A wooden door opens to a cozy living area, with rustic elements seen through the doorway.
Home in Beaconsfield
4.9 out of 5 average rating, 52 reviews

The Crafty Fox Beaconsfield

The Crafty Fox is a Luxury 2-bed Grade II listed cottage in the heart of Beaconsfield Old Town. Recently renovated to a high spec, with elegant interiors, a private courtyard garden, and secluded hot tub. Walk to top restaurants, bars, and shops. Easy access to London (under 30 mins), Cliveden House, and Hedsor House. Just 35 minutes from Bicester Village. Perfect for romantic getaways, weddings, or stylish countryside escapes.

Guest favourite
The exterior of the building is shown with a large flowering tree in full bloom. The staircase leading to the first floor accommodation is visible alongside lush greenery and garden beds featuring blooming flowers. A clear blue sky adds to the serene country setting.
Barn in Buckinghamshire
4.96 out of 5 average rating, 841 reviews

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.

Guest favourite
The exterior of the detached studio is displayed, featuring a modern facade with large glass doors that invite natural light. A well-maintained gravel pathway leads to the entrance, flanked by neatly trimmed shrubs, creating an accessible approach.
Tiny home in Loudwater
4.92 out of 5 average rating, 71 reviews

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

When is the best time to visit Penn?

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Avg. price$138 SGD$154 SGD$159 SGD$199 SGD$136 SGD$131 SGD$173 SGD$173 SGD$119 SGD$116 SGD$147 SGD$146 SGD
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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.

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