Vacation rentals in Penn Street

4.96 out of 5 average rating, 349 reviews

A spacious garden area is depicted, featuring well-maintained grass and an array of colorful shrubs and flowers. Lush green trees provide shade, while the historic building with a charming roof is visible in the background, adding character to the serene outdoor space.

Guest suite in Amersham

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.

Treehouse in Hertfordshire

The outdoor balcony features two wooden chairs and a small table, partially surrounded by trees. A relaxed setting is created, with a towel draped around an individual seated at the table. A hot tub is visible nearby, offering a tranquil view of the surrounding forest.

4.94 out of 5 average rating, 174 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!

Bungalow in Buckinghamshire

A sunset casts a soft glow over rolling hills, with vibrant colors painting the sky. In the foreground, a flowering plant rests among lush greenery, adding a touch of natural beauty to the serene landscape.

4.86 out of 5 average rating, 216 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.

Guest suite in Buckinghamshire

A charming high street scene is captured, with traditional brick buildings lining both sides. Colorful bunting is strung overhead, and parked cars are visible along the road. Potted plants add greenery to the environment, enhancing the inviting atmosphere of this vibrant area.

4.97 out of 5 average rating, 108 reviews

Bright self-contained annexe with its own garden

This recently renovated, self-contained, quiet and bright annexe has everything you need for a relaxing stay in the Chilterns. It offers own entrance, open plan living area with a kitchen and a small table, bathroom and a bedroom with a king sized bed. Enjoy your morning coffee or a picnic in the sunshine in your own little garden with table and comfortable chairs. Conveniently located, only 8 min walk to Amersham station and 1 min walk to the high street with many cafes, shops and restaurants.

4.98 out of 5 average rating, 110 reviews

A wooden hot tub filled with bubbling water is set against a backdrop of lush greenery. The glass-walled pool house is visible behind, with an inviting swimming pool nearby. The area features a serene and private outdoor space designed for relaxation.

Barn in Buckinghamshire

Period barn, private heated swimming pool, hot tub

This magnificent country property, complete with an award winning heated pool complex is set high in the chiltern hills, bordering an area of outstanding natural beauty yet located only half a mile from the London Underground Met Line and Waitrose! Explore acres of orchards, formal and walled gardens, a lake, pergolas, and wild meadows, surrounded by ancient woodland and farmland. Escape to heaven in this spa like tranquil retreat. Leave your stress behind and visit this high tech masterpiece.

4.81 out of 5 average rating, 168 reviews

A spacious outdoor patio area features wooden lounge chairs and a low table, overlooking a lush meadow garden. Natural light pours in through the open space, highlighting the sleek concrete floor and landscaped surroundings. Trees and open fields extend into the distance.

Home in Seer Green

Modern Eco-Annex set within Meadow

We would love to welcome you to stay in our peaceful and modern self-contained property set with 1.6 acres of meadow garden. The house has been designed to make the most of the natural light and surroundings. The property is adjacent to the main house, is completely detached, and is separated by a large courtyard ensuring guests have complete privacy. A perfect place to escape into nature, visit historic towns and villages, or base yourself to work remotely with easy access to central London.

Guest suite in Buckinghamshire

A private outdoor seating area is featured, surrounded by greenery. Two wooden chairs are positioned on a grassy patch, with a gravel pathway leading to a wooden structure. The tranquil space offers a suitable spot for relaxation in the garden.

4.95 out of 5 average rating, 301 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.

4.99 out of 5 average rating, 102 reviews

A small, private patio area is shown with a wooden bistro table and two folding chairs. French doors lead into the apartment, framed by brick walls and greenery. The surrounding space features paved flooring and a wooden fence, providing a sense of seclusion.

Guest suite in Amersham

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.

4.99 out of 5 average rating, 139 reviews

A serene forest scene is presented, featuring tall trees surrounded by a vibrant carpet of bluebells. The sunlight filters through the lush green canopy, creating a peaceful atmosphere among the diverse foliage.

Cottage in Amersham

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.

Cottage in Buckinghamshire

The entrance to The Cottage is framed by a charming red brick wall. A white wooden door stands centrally, featuring a window with grid patterns. A black door knocker and a decorative plaque identify the property. Colorful flower baskets hang beside the door, adding warmth.

4.9 out of 5 average rating, 128 reviews

The Cottage in Old Amersham

THE COTTAGE is a well equipped home that sleeps up to 6 guests and is tucked away just off the High Street in the beautiful small historic town of Old Amersham. There's a great choice of restaurants and pubs and a large supermarket all within walking distance. The Cottage has a bus stop a minutes walk away and a 20 minute walk/short drive to the train station (direct service in to London). The Cottage is the perfect space for couples, friends, business travellers, and families.

Tiny home in Holmer Green

A serene woodland scene is depicted, filled with vibrant greenery and an expanse of bluebells carpeting the ground. Tall trees create a natural canopy, with sunlight filtering through the leaves, casting gentle shadows on the lush grass.

4.98 out of 5 average rating, 154 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.

Casa particular in Wendover

An outdoor seating area is set with two glasses of white wine beside a glowing lantern on a marble table. Soft string lights can be seen along the fence, and a view of open fields is framed under a twilight sky with a full moon.

4.91 out of 5 average rating, 275 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. The surrounding area has some renowned country walks and cycle paths.

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Other great vacation rentals in Penn Street

4.88 out of 5 average rating, 16 reviews

A modern bathroom features elegant stone walls and flooring. A spacious walk-in shower is visible, equipped with a rainfall showerhead. A stylish double sink vanity with sculptural basins sits against the wall, complemented by soft ambient lighting that highlights the bathroom's contemporary design.

Home in Hastoe

Honey Barn - Stunning 4-Bed Rural Paradise

AlexRating, 5 stars1 week ago

We had an absolutely fantastic experience, everything worked smoothly, and there were no issues at all. The space was immaculate and welcoming, just as described, and we loved how comfortable and thoughtfully prepared everything was. Communication with the host was great, with quick responses and clear instructions. You can even message the lovely owner personally who accommodated a late check out for us. We felt well taken care of throughout our stay. The location couldn’t have been better, close to key tring (5 min drive) yet delightfully peaceful for a relaxing getaway. From the cleanliness to the seamless check-in, every detail was spot on. Highly recommend this place for anyone looking for a perfect, hassle-free stay in Hastoe. We’d love to come back!

4.86 out of 5 average rating, 70 reviews

Barn in Walter's Ash

Bradenham Barn in The Chiltern Hills

EmilyRating, 5 stars1 week ago

What a beautiful and memorable stay! This home is bigger than it looks in the photos — lots of room to lounge. I would agree with previous reviews about noise level being close to the road. Otherwise the loveliest stay!

Apartment in Buckinghamshire

A ground floor flat is illuminated by natural light from double doors leading to a private patio. Inside, contemporary furnishings include a small dining table, a cozy sofa, and a well-equipped kitchen featuring modern appliances, including a washing machine.

4.96 out of 5 average rating, 28 reviews

Flat Beaconsfield Bucks UK patio & free parking

Laird ChrisRating, 5 stars1 week ago

lovely place, lovely host!

A view of the exterior of the cottage reveals a charming wooden facade with multiple windows, allowing natural light to enter. The open doorway leads to a modern kitchen adorned with sleek appliances and a functional layout. A paved area is visible, offering a practical outdoor space.

Barn in Buckinghamshire

4.67 out of 5 average rating, 3 reviews

The Potting Shed

AnnemarieRating, 5 stars1 week ago

The Potting Shed is a beautiful space, very clean, cosy & has the benefit of parking as well as being close to the local amenities. I’d not hesitate to recommend & Paul’s communication was excellent. The little touches like tea, coffee, wine & biscuits were very much appreciated.

4.98 out of 5 average rating, 94 reviews

An open-plan living area features wooden walls and large glass windows, allowing natural light to fill the space. A compact kitchen with dark cabinetry is present, alongside a round table with two woven chairs. A doorway leads to the exterior, enhancing the connection to nature.

Cabin in Oxfordshire

The Mirror Houses - Cubley

CameronRating, 5 stars2 weeks ago

We had the most wonderful stay at the Mirror Houses in Oxford. From the moment we arrived, everything felt peaceful, welcoming, and beautifully thought-out. The cabin itself is stunning — immaculately clean, stylish, and so cosy, with everything we needed and more. The hot tub was a real highlight, especially in the evenings when we could unwind and take in the surroundings. Lucy was an exceptional host — warm, thoughtful, and incredibly helpful throughout. Travelling with our 9-week-old baby, we were a little nervous, but Lucy went above and beyond to make sure we were comfortable and had everything we needed. Her kindness and attention to detail genuinely made our stay feel special and memorable. We left feeling relaxed, grateful, and already talking about when we might come back. A perfect little retreat — we couldn’t recommend it more

5 out of 5 average rating, 3 reviews

A scenic view along the River Thames showcases softly rippling water and moored boats. Lush green trees line the bank, providing shade, while a wooden walkway invites leisurely strolls. The image features waterfront homes in the background, adding to the serene atmosphere.

Apartment in Bourne End

Cozy and stylish private Studio Apartment

NinaRating, 5 stars3 weeks ago

Sophies place had everything I was looking for, somehwere quiet and comfortable to get a good nights sleep. The place was very clean and Sophie was very prompt in her responses to my questions. Well worth the money and I would definitely book this place again when I'm back in the area.

4.95 out of 5 average rating, 44 reviews

A spacious living area is shown with large glass doors opening to a verdant view. Wooden accents on the wall complement modern furnishings, including a dining table and a sleek kitchenette. A comfortable sofa is positioned toward a work desk, creating an inviting atmosphere.

Barn in Buckinghamshire

The Stables

SarahRating, 5 stars4 days ago

A perfect place to spend a couple of nights within reach of the annual Midsummer (chamber) Music Festival in Old Amersham. Essential to have a car, but that was because of the peaceful surroundings just outside Chesham.