Holiday rentals in Penn

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Top-rated holiday rentals in Penn

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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
4.86 out of 5 average rating, 234 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 spacious open-plan living room features large windows framing views of the surrounding greenery. A comfortable seating arrangement includes two sofas and a central coffee table. A decorative ladder leads to the mezzanine, which accommodates a King size bed. Soft lighting enhances the cabin's inviting feel.
Cabin
4.96 out of 5 average rating, 1,668 reviews

Romantic Oak Cabin Berkhamsted

This cosy luxurious self contained oak framed cabin offers the perfect peaceful setting for a relaxing getaway. Listen out and you may hear the owls at night. Backing onto the National Trust Ashridge Forest, perfect for outdoor lovers yet equally suitable for a romantic night in. 1.5 miles away, the popular market town of Berkhamsted, offering atmospheric pubs and bars for a special night out. The cabin offers cozy spacious living with King size bed on a mezzanine floor! STRICT NO PET POLICY!

Top guest favourite
A charming cottage is set in a green landscape, featuring a sloped roof and dark exterior walls. The front porch is accessible by steps and showcases a small seating area with a table and chairs. Large windows allow natural light to brighten the entrance.
Barn
4.98 out of 5 average rating, 387 reviews

The Stables in Historic Berkhamsted

Welcome to one of the most historic parts of Berkhamsted - the hilltop site of Old Berkhamsted Place, and the original Grade 2* listed barn which remains, reputedly, the largest medieval barn in the counties of Beds, Bucks & Herts. The Stables is a spotlessly chic cottage for 2 with large gardens & parking, offering luxury linen & towels, wi-fi & TV. Ideal town/country position - 10mins walk to town centre with cafes, restos, boutiques and antique stores, and train to London is only 35mins!

Top guest favourite
The exterior of Chiltern Barn is depicted, showcasing a two-story building with a slate roof and natural stone façade. Large glass doors open onto a stone patio area, and a cobbled courtyard is visible in front, framed by lush greenery and a clear blue sky.
Cottage
4.97 out of 5 average rating, 351 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

Chiltern Barn is a 230 year old converted hay barn in Wheeler End in Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames with easy access to the M40. Wheeler End is a small village in The Chilterns built around a large common. There is a friendly local pub, The Chequers and Lane End, less than mile away has local amenities, including a well stocked Londis, a newsagents, excellent farm shop, gastro-pub, Indian and Chinese takeaways, hair dressers etc.

Top guest favourite
An inviting bedroom features a spacious bed adorned with a floral-patterned duvet cover. Soft lighting from two bedside lamps creates a calming ambiance. The room showcases a unique triangular window design, enhancing the architectural interest of the space.
Guest house
4.99 out of 5 average rating, 218 reviews

The Ridgeway Lodge close to Ivinghoe Beacon

The Lodge is a separate building from the main house and has a private patio for relaxing in the sunshine or stargazing at night. The double doors from the patio, lead you into the main, open plan kitchen / living room / dining area. There is a sofa bed with large TV with immediate access to Netflix, iPlayer etc, and super fast WiFi. There is a downstairs loo. Upstairs there is a double bedroom with en-suite bathroom and shower. It has all the amenities for a comfortable and relaxing stay.

Guest favourite
A spacious bed is adorned with a decorative black-and-white blanket and an array of decorative cushions. Two nightstands with lamps are positioned on either side, providing balanced lighting. Natural light enters through a window fitted with dark blinds.
Guest suite
4.9 out of 5 average rating, 427 reviews

Southwood Gardens annexe in Cookham

We are right on the edge of the beautiful village of Cookham. The accommodation is annexed to the main house and is accessed through a secured side-gate for total privacy. There is also free private parking on the front drive. The room is ideal for people who need to commute (1 hour by train to London, 25 minutes drive to Heathrow), or families who need to have additional accommodation for their loved ones to stay in the area. We very much look forward to welcoming you to Cookham soon !

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
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
4.97 out of 5 average rating, 228 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
4.93 out of 5 average rating, 130 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
4.87 out of 5 average rating, 166 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..

Top 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
4.98 out of 5 average rating, 324 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 serene landscape unfolds with gentle hills and lush greenery, set against a vibrant sunset sky. The foreground features a rustic brick wall, partially covered by grass and wildflowers, providing a natural boundary to the expansive fields beyond.
Home
4.9 out of 5 average rating, 136 reviews

Gorgeous Cottage in Skirmett with Parking

This gorgeous 3 bedroom cottage, is in the quiet village of Skirmett, situated in the Hambleden Valley, in a particularly pretty area of the Chilterns. Many films and TV series have been filmed in the area, as it is often thought of as quintessentially English. Just a hop and a skip from London and its airports and a short distance from Marlow, Henley or High Wycombe stations... come and step back in time and enjoy a rural setting you won't forget.

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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