Holiday rentals in Penn

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Penn

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
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, 373 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 in Marlow
5 out of 5 average rating, 124 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
The exterior of the studio is displayed during a sunset, with a warm pink sky glowing above. A conservatory with large windows is visible, surrounded by a lush garden featuring blooming flowers and green grass. The countryside backdrop includes distant trees and open fields.
Home in Buckinghamshire
4.85 out of 5 average rating, 178 reviews

Stunning riverside house in the heart of Chilterns

Unique opportunity to stay in the heart of the stunning Chilterns only 30 mins from London. The River Chess flows past the bedroom with wonderful views of countryside beyond. Property offers large sitting/dining room (dbl sofa bed) wet room, kitchen & sunny conservatory. Fibre broadband. Glorious walking on Chess Valley Walk. Nearby Amersham, Chalfont, Chesham & Chenies all offer superb restaurants/pubs/shops & Met line tube to Baker St/Marylebone. Harry Potter World 15min, Heathrow 25min away

Top guest favourite
A spacious lounge area is showcased with a plush green sectional sofa, light streaming through skylights. A large flat-screen TV is mounted on the wall, while a sleek coffee table sits atop a colorful area rug. Bright throw pillows add comfort, complemented by a dining space visible in the background.
Flat in Buckinghamshire
4.99 out of 5 average rating, 404 reviews

Apartment 24 GERRARDS CROSS

Delightful fully self-contained luxury one double bed apartment with own private entrance (your host is an interior designer). 10 minute level walk to Gerrards Cross village with a vast variety of restaurants, supermarkets and shops. Located 25 minutes from London Marylebone by use of Chiltern Railway Services at Gerrards Cross Station (10-15 minute walk from property) and no more than 40 minute drive from London Heathrow. This accommodation will provide a home away from home experience.

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 Buckinghamshire
4.95 out of 5 average rating, 341 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
The entrance of the studio apartment features a charming brick façade adorned with vibrant flowers. A small wooden bench sits on a stone patio, flanked by decorative planters filled with blossoms. A white front door with glass panels invites guests into the cozy space.
Guest suite in Amersham
4.99 out of 5 average rating, 128 reviews

Renearth - Private, modern double bed studio apt.

Our ground floor studio apartment is conveniently located to Amersham town centre with easy access to London via the Metropolitan and Chiltern lines. The apartment is attached to our house with its own private entrance. It consists of a fully fitted kitchen, spacious bathroom, comfortable, cosy bedroom and its own secluded patio. Located in a quiet Close, with footpath access to Amersham town centre with numerous shops and restaurants. Close by is the historic town of Old Amersham.

Top guest favourite
An airy living space is highlighted by high ceilings and natural light streaming through large windows. A mix of seating options, including a gray sofa and a white armchair, surrounds a coffee table. A dining area with white chairs complements a gray sideboard.
Cottage in Amersham
4.97 out of 5 average rating, 159 reviews

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.

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, 220 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
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, 129 reviews

Stunning One Bedroom Annex

The annex is very cosy. The bedroom has ensuite and there is a separate living room with a very comfy sofa. There is a garden and outside dining table. 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 all places in Buckinghamshire as well as to London. The location is very peaceful.

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 Wooburn Green
4.9 out of 5 average rating, 199 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!

Guest favourite
The studio features a modern double bed positioned centrally, framed by softly lit sconces on the wall. Natural light enters through a window adorned with light curtains. A small desk and chair are placed beside the bed, complemented by a dark, textured rug on the wooden floor.
Flat in Buckinghamshire
4.94 out of 5 average rating, 333 reviews

Budget Bliss in High Wycombe

A unit on its own, away from the main residence, this is a modern, comfortable annexe with a high-end finish. Ideal for people working in the area, short stops or longer stays. Even for those looking for long country walks and a home away from home for some peace and quiet downtime. Ensuite with a double bed, kitchenette with 2 burner hob, fridge freezer, microwave and lots of storage with a separate built in wardrobe. Sleeps 2 comfortably.

Top 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, 802 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.

Popular amenities for Penn holiday rentals

When is the best time to visit Penn?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$132 SGD$127 SGD$130 SGD$195 SGD$133 SGD$128 SGD$170 SGD$170 SGD$116 SGD$114 SGD$144 SGD$143 SGD
Avg. temp5°C5°C8°C10°C13°C16°C18°C18°C15°C12°C8°C5°C

Frequently Asked Questions

  • 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.

  • What are the most popular amenities for House Rentals in Penn?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with a kitchen, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

  • 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.

  • 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.

  • 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.

  • Do house rentals in Penn have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Penn. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Penn?

    Make yourself at home in Penn by choosing from our most frequently booked neighborhoods. We have over 270 vacation rentals in Penn, over 120 vacation rentals in Winchmore Hill, and over 120 vacation rentals in Knotty Green.

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 $51 SGD 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

  1. Airbnb
  2. United Kingdom
  3. England
  4. Buckinghamshire
  5. Penn