Holiday rentals in Penn

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Top-rated holiday rentals in Penn

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

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Guest favourite
Casa particular in Wendover
4.9 out of 5 average rating, 314 reviews

The Nook at Pine View - set in Roald Dahl Country

The Nook at Pine View, is set within the Chiltern Hills in a designated Area of Outstanding Natural Beauty. In the heart of "Roald Dahl Country", Cobblers Hill is famously written within the pages of "Danny Champion of the World". The Nook benefits from stunning rural views and the peace & quiet of country living but with easy access to award-winning restaurants, pubs & cafes all just a short drive. A 45 min train to London. The surrounding area has some renowned country walks and cycle paths.

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, 375 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 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, 180 reviews

Stunning riverside house in the heart of Chilterns

Breathtaking location set in the heart of stunning Chilterns countryside only 30 min from London. Come & recharge with views of the River Chess flowing past your bedroom. Relax in the large sitting/dining room (dbl sofa bed) or bask in the sunny conservatory watching swans glide by. Glorious walking on Chess Valley Walk. Nearby Amersham, Chalfont & Chenies all offer superb restaurants/shops & Met line tube. Amazing location just off M25 - Harry Potter World 15min, Heathrow 25min & Ascot 45 min.

Top guest favourite
Flat in Windsor and Maidenhead
4.97 out of 5 average rating, 257 reviews

The Studio in Maidenhead Riverside, Berkshire, UK.

LARGE STUDIO: (T0) A large self-contained quiet studio with UK size 2m double bed, en-suite bathroom and kitchenette with it's own private entrance. Attached to our house. There is off-street parking for 1 guest car. Convenient for the A4, M4, M40 M25 London is 25 miles. Heathrow Airport is 15 minutes away by car.. Direct trains into London. The Elizabeth Line train runs from Maidenhead station direct to London and the West End. Good for Windsor, Ascot, River Thames, Pinewood Studios etc.

Top guest favourite
Flat in Buckinghamshire
4.99 out of 5 average rating, 408 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 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, 129 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
Tiny home in Holmer Green
4.97 out of 5 average rating, 226 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
An outdoor dining area is displayed, featuring a glass-top table surrounded by four wicker chairs. A patterned rug is placed beneath the table, providing a designated space on the stone-paved patio. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.
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.

Guest favourite
A modern living area features a stylish seating arrangement with a plush yellow ottoman and a grey sofa. A marble-topped coffee table sits in front, complemented by a flat-screen TV and a wall-mounted clock. The open kitchen area is visible, outfitted with sleek cabinetry.
Flat in Downley
4.87 out of 5 average rating, 165 reviews

The High Street Gallery,

Brand new and renovated to a high standard, This fully fitted apartment is spacious and stylish,everything you need for a nice relaxing stay will all amenities on your doorstep and a good wifi connection, Perfectly located for Downley Common and access to the Chilterns, Hughenden Manor is within walking distance and the Hellfire Caves at West Wycombe are also close by, There is a bus stop outside the property for easy access to High Wycombe town centre..

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, 336 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
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, 188 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 house rentals in Penn have a kitchen?

    Absolutely! We offer over 20 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 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.

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

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