Holiday rentals in Penn

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Top-rated holiday rentals in Penn

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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 in Amersham
4.96 out of 5 average rating, 376 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
A rustic treehouse is elevated among leafy trees, connected by a wooden staircase. Surrounding foliage creates a serene environment, while a shaded area beneath features a bench and a fire pit. The natural setting offers a sense of privacy and tranquility.
Treehouse in Hertfordshire
4.96 out of 5 average rating, 254 reviews

Tree House - Hot Tub on balcony

Our rustic Glamping Treehouse stands 5m above the ground, which is accessible via an exciting seven-meter long suspension bridge. Boasting a warm themed interior, the Treehouse offers breathtaking views over the Chess Valley, which can be seen from the balcony and through the large panoramic window. Features include a spacious king-size double bed, en-suite toilet and basin facility. The outdoor balcony is home to a shower and hot tub, the perfect spot to relax amongst the surrounding treetops!

Top guest favourite
A cozy bedroom features a spacious bed dressed in soft blue linens, flanked by wooden nightstands with blue lamps. Exposed wooden beams add character to the sloped ceiling, and natural light enters through the window, complemented by a neutral carpet flooring.
Guest house in Croxley Green
4.99 out of 5 average rating, 224 reviews

Near business park, tube, Harry Potter airports.

This is a traditional old stable building which does make it unsuitable for disabled access. The location is situated in a quiet area with its own secure parking and easy access to transport links. Croxley business park is a 5 minute drive away. The motorway is a ten minute drive away. London underground metropolitan line is a ten minute walk. Wembley is a 20 minute tube ride. Heathrow airport is a 15 minute drive, Luton airport is a 25 minute drive, Harry Potter world is a 10 minute drive.

Top guest favourite
A serene scene showcases a cottage surrounded by lush greenery and a private lake. Two swans glide across the calm water, while the cottage, with its wooden facade and sloped roof, is nestled among the trees, offering a peaceful retreat in nature.
Cottage in Sarratt
5 out of 5 average rating, 264 reviews

Crestyl Cottage riverside barn for 2 with hot tub

Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.

Top guest favourite
The exterior of a self-contained suite is depicted, featuring a dark wooden facade with a pitched roof. A simple entrance door is framed by greenery, including shrubs and small plants that line the pathway. The surrounding lawn is well-maintained, creating an inviting approach.
Guest suite in Little Missenden
4.95 out of 5 average rating, 345 reviews

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.

Top 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, 425 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
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
4.93 out of 5 average rating, 130 reviews

Stunning One Bedroom Annex

The annex is very cosy with free parking on front drive. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table and gazebo area at the bottom ideal for smokers. 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 locations.

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 Little Missenden
4.97 out of 5 average rating, 232 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.

Top guest favourite
The historic windmill stands majestically against a backdrop of open skies, featuring a stone façade and a brick band near the top. A wooden door leads to the entrance, flanked by a gravel pathway. Lush greenery and fields are visible in the distance, enhancing the rural setting.
Windmill in Oxfordshire
4.98 out of 5 average rating, 222 reviews

The Windmill Blackthorn Hill, Nr. Bicester Village

Featured in the 'Times Newspaper' Top 10 best Places to Stay with Spectacular Views: "A truly amazing experience." Enjoy a luxurious stay in a historic 17th c. listed windmill and create unforgettable memories. You won’t be short of things to do—enjoy boutique shopping at the renowned Bicester Village or take leisurely walks around historic Oxford, just a 15-minute train ride away. Additionally, Blenheim Palace and Waddesdon Manor are nearby attractions worth exploring.

Top guest favourite
A well-lit living area features a comfortable gray sofa paired with a matching ottoman. Two side tables with lamps are situated next to large windows, which allow natural light to fill the space. A small desk with a chair completes the setup.
Apartment in Marlow
4.92 out of 5 average rating, 418 reviews

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)

Top guest favourite
The cottage features a charming brick and flint exterior, adorned with climbing foliage and pink flowers. A vibrant blue front door adds a pop of color, while the well-maintained garden includes lush greenery. Windows are symmetrically placed, allowing for generous natural light.
Home in Beaconsfield
4.91 out of 5 average rating, 209 reviews

18th century cottage

Self contained character annex in the beautiful Buckinghamshire countryside. Low ceilings and a narrow steep staircase with handrail and stair gates top and bottom. Parking spaces at the front and use of the pretty garden to the rear. Fantastic location on the edge of the Chilterns; good road and rail links to London and Oxford, close to the Thames, Windsor, Marlow, Cliveden, Hedsor House, Harry Potter Studios and Legoland. Plus there’s a pub next door!

Top guest favourite
A charming exterior view of Red Kite Barn features a landscaped garden bordered by a wooden lattice fence. Colorful flowers and greenery enhance the inviting entrance. The gravel driveway leads to the barn's private entrance, set amidst a serene natural landscape.
Guest house in Buckinghamshire
5 out of 5 average rating, 189 reviews

Red Kite Barn in a secluded valley close to Marlow

Red Kite Barn is situated in a lovely secluded valley (AONB), a 5 minute drive (25min walk) into Marlow, with its coffee shops, riverside walks and Michelin star dining. We are perfectly located for cycling or walking in the beautiful Chilterns and a short drive from Henley and Windsor. Heathrow is half an hour and fast trains go into London from Maidenhead. Red Kites, squirrels, foxes and deer are regular visitors to the garden.

Popular amenities for Penn holiday rentals

When is the best time to visit Penn?

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Frequently Asked Questions

  • 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.

  • 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 20 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.

  • 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 270 vacation rentals in Penn.

  • 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.

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 £30 per night before taxes and fees

  • Verified guest reviews

    Over 1,580 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 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

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