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 €26 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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Top guest favourite
A bright kitchen scene is visible through a set of white-framed windows, showcasing a lush garden outside. A stainless steel sink and drying rack are positioned in the foreground, reflecting natural light. The garden features greenery and blooming flowers, creating a calming view.
Guest suite
4.96 out of 5 average rating, 390 reviews

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.

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
5 out of 5 average rating, 142 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
4.93 out of 5 average rating, 173 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
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
5 out of 5 average rating, 21 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
4.97 out of 5 average rating, 275 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.

Superhost
Home
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 cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage
4.97 out of 5 average rating, 353 reviews

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

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
4.91 out of 5 average rating, 54 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
4.96 out of 5 average rating, 844 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
4.92 out of 5 average rating, 73 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.

Top guest favourite
A bright open-plan seating area features a large grey settee adorned with yellow accent pillows. A small coffee table sits in front, complemented by a sleek cabinet and a wall-mounted TV. Bifold doors lead out to a private patio with garden views.
Home
4.98 out of 5 average rating, 104 reviews

Home in Marlow

If you’re looking for a quiet central location (with the luxury of parking), in a spacious and stylish modern newly renovated extension then this is the place for you! Whether you're looking to relax and unwind or enjoy the many bars, restaurants and shops that Marlow has to offer, this is a great place to stay.

Guest favourite
A bell tent is positioned on a grassy field, adorned with bunting and a sunflower nearby. Inside, a double bed and single bed are visible, both dressed with bedding. The entrance is framed by a welcoming view of the surrounding greenery.
Tent
4.85 out of 5 average rating, 107 reviews

Comfy boho bell tent on farm in Penn.

This bell tent, Freddie, on our farm just outside Beaconsfield has a double bed and single bed, which are all dressed with bedding, and is lit by fairy lights. We allow campfires, and there is a famous old pub, The Royal Standard of England, just along the footpath from the farm...

Popular amenities for Penn holiday rentals

When is the best time to visit Penn?

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Avg. price€94€105€108€135€92€89€118€118€81€79€100€99
Avg. temp5°C5°C8°C10°C13°C16°C18°C18°C15°C12°C8°C5°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 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 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 wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

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