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, 360 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.

Guest favourite
The outdoor dining area features a table with four chairs under a green umbrella. Potted plants frame the space, and the background showcases large glass doors leading into the bungalow. Bright greenery and clear skies enhance the comfortable setting.
Bungalow in Buckinghamshire
4.87 out of 5 average rating, 227 reviews

Stunning Chiltern Views from Old Amersham Bungalow

NEW BUNGALOW Kyteway is a self-contained detached studio between the historic town of Old Amersham and the rolling Chiltern Hills. Offering fully equipped kitchen, spacious shower room, double bed in sleeping area, dining table, storage, and sofa bed. BEAUTIFUL VIEWS from private dining patio & separate sun terrace. Short walk to historic old town and easy access to new town (inc station to London) on foot, by car, or local bus. Adjacent to countryside footpaths. Unrestricted on-street parking.

Top 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.
Farm stay in Buckinghamshire
4.85 out of 5 average rating, 159 reviews

Stunning spacious Riverside House in the Chilterns

Stunning Riverside house with modern & spacious living. River Chess flows outside the king size bedroom with wonderful views of the countryside beyond. The property includes wet room, kitchen, huge sitting/dining room (double sofa bed) fibre broadband & beautiful conservatory with views to a second river. There is private access to the Chess Valley walk. Nearby Amersham, Chesham & Chalfont Underground take you to London in 30 mins. Harry Potter World is 15min away. Heathrow is 25 mins away

Guest favourite
A charming exterior view of the one-bedroom annexe is presented, featuring a welcoming entrance with a wooden door surrounded by lush greenery and flower pots. A gravel pathway leads to the entrance, framed by large windows that allow natural light into the space.
Home in Flackwell Heath
4.89 out of 5 average rating, 125 reviews

1 bed apartment. Village location. Heathrow 25mins

This one bedroom apartment is annexed within our family home but benefits from its own entrance and facilities. Quiet village location but easy access to transport links (Heathrow is 20 mins drive, London 35 mins on the train). We are on the edge of the Chilterns, an UNESCO recognised Area of Outstanding Natural Beauty. We are taking bookings using the Covid19 guidelines and legislation set out on the UK government website. If the road map changes then availability may also need to change.

Guest favourite
A bright studio space features a spacious bed with crisp white linen, set against a backdrop of exposed wooden beams. A comfortable sofa is nearby, and sliding glass doors offer views of the garden, enhancing the feeling of openness and light.
Guest house in Cookham
4.89 out of 5 average rating, 548 reviews

Riverside Boathouse

A warm and cosy studio style converted boat house on the edge of the River Thames in Cookham, Berkshire. Separate from the main house, the double glazed studio boathouse with en-suite, decorated beautifully. Egyptian cotton linen and nice towels. Relax with views of the river. Blackout blinds, kitchen, en-suite shower room, fridge, double glazing, heating, TV, WIFI, laptop area, outdoor seating/picnic blanket, umbrellas, off road parking, boat mooring, EV Charging Point (fee applies).

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, 327 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, 119 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
4.98 out of 5 average rating, 155 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
4.98 out of 5 average rating, 197 reviews

The Stable Lodge

The Lodge is light, airy and modern, whilst providing original character and features. An ideal romantic 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
4.92 out of 5 average rating, 119 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
A charming wooden barn is set amidst lush greenery and tall trees. A tranquil pond with water lilies reflects the surrounding foliage. Bright sunlight illuminates the scene, enhancing the peaceful outdoor space and the rustic charm of the barn.
Guest house in Buckinghamshire
4.98 out of 5 average rating, 257 reviews

The Barn at The Grove

The Barn is a self-contained recently converted space in the heart of the Chilterns. It is close to the riverside towns of Henley-on-Thames and Marlow and the surrounding Chiltern countryside. It is located on the edge of the village of Frieth with nearby farm shops and local gastro-pubs within a 5 min drive. The Barn is in a private and peaceful location with off-street parking. It is perfect for couples, solo travellers and small families.

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, 315 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.

Popular amenities for Penn holiday rentals

When is the best time to visit Penn?

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Avg. price$135 SGD$130 SGD$134 SGD$200 SGD$136 SGD$131 SGD$161 SGD$164 SGD$145 SGD$197 SGD$147 SGD$160 SGD
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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 $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,470 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

  • 4.8 Average rating

    Penn stays are highly rated by guests – averaging 4.8 out of 5!

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