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Vacation rentals in Penn Street

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Top-rated vacation rentals in Penn Street

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Superhost
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 Amersham
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 favorite
An open plan living area features a dark sectional sofa adorned with decorative pillows. A round dining table is positioned nearby, topped with a vase of fresh flowers. Natural light filters through the window, highlighting the wooden beams and staircase.
Guesthouse in Sarratt
4.93 out of 5 average rating, 135 reviews

Charming 1 bedroom annex in a rural location

A self contained annex that can accommodate up to 4. The top floor is given over to the main double bedroom with views over the nearby woodland, while downstairs is a bathroom & open plan kitchen/ living area with a sofa bed that can sleep a further 2 people. The annex has dedicated parking & outside patio which makes the most of the countryside location. It is close by The Grove hotel, The Wizarding World of Harry Potter, Leavesden film studios, & links to London via public transport & the M25

Top guest favorite
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 Amersham
4.85 out of 5 average rating, 185 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.

Guest favorite
The bright living area features vaulted ceilings with original wooden beams and skylights. A comfortable sofa sits beside a soft ottoman, while a white coffee table holds decorative items. Large glass doors lead to an outdoor space, and a wall-mounted TV is positioned for viewing.
Barn in Princes Risborough
4.96 out of 5 average rating, 343 reviews

Beautiful cosy Scandi-barn in Chiltern market town

A beautiful, calm and cosy space designed to feel like a home from home. Lovingly updated and modernised, whilst retaining original character and features to create a unique guest experience. Uber-clean and free from clutter, everything looks & feels fresh for each stay. The kitchen, carpets, paintwork, doors, windows and VELUX roof-lights have been replaced or updated recently. Located with a parking space in a secure, gated courtyard just moments from the town centre of Princes Risborough.

Guest favorite
A wooden cabin with an arched design is framed by tall trees, creating a natural setting. Steps lead to a spacious deck area, which includes potted plants and a dark wood BBQ grill under a covered space.
Tiny home in Buckinghamshire
4.97 out of 5 average rating, 816 reviews

The Woodland Cabin with Private Hot Tub Spa

Step into a world of peace and privacy in a secluded cabin. The perfect setting for romance, relaxation and a touch of luxury. Soak under the stars in the private hot tub, cozy up by the wood burner, the scent of countryside air and the sound of birdsong. With a comfy double bed, fitted bathroom, kitchenette, gas BBQ. Surrounded by scenic walking trails, charming pubs, and nearby heritage spots, this is the perfect romantic retreat to slow down, reconnect, and create unforgettable memories.

Top guest favorite
A spacious bedroom is presented with a king-size bed adorned with hotel-quality linens. Flanking the bed are two bedside lamps providing soft illumination. A vintage dressing table and chair are positioned nearby, complemented by a stack of antique suitcases at the foot of the bed.
Cottage in Brill
4.88 out of 5 average rating, 153 reviews

Elegant Countryside Cottage near Oxford

Spacious and beautifully finished countryside cottage in the heart of Brill village with views across the village green and just a 2 min walk from The Pointer pub. The perfect base for exploring the countryside, Oxford, Thame and Bicester Village. Blenheim Palace, Waddesdon Manor, the Cotswolds, Silverstone race track and London are all within easy reach. Well behaved dogs over 2 years old welcome! * Host My House manages this property which is owned by Christopher & Gillian Scott-Mackirdy *

Top guest favorite
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.
Apartment in Gerrards Cross
4.99 out of 5 average rating, 412 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.

Superhost
A charming exterior of a two-story barn is nestled among greenery and flowering plants. The roof features wooden shingles, and the upper windows allow natural light to flood in, showcasing a serene landscape of rolling hills and fields in the background.
Home in Ipsden
4.88 out of 5 average rating, 214 reviews

The Old Barn , Organic Residence, outside seating

2 x king size organic bedroom-en-suites, with off street parking, great base for work or vacation, my Italian cousin Angelo, calls it " Tuscany in the Chilterns " home to "Midsummer Murders" ,"Wind in the Willows" and Agatha Christie's, "Miss Marple & Poirot mysteries", 200 year old country barn two fields from the Thames, beautiful views, and one of a few areas in the UK where you have hills and valleys and a navigable river wrapping around them, encircled by picturesque riverside towns

Top guest favorite
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 Little Missenden
4.95 out of 5 average rating, 345 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 favorite
The exterior of Applewood Cottage is depicted with a blend of traditional and modern architecture. Expansive grassy areas are visible, along with a patio space featuring outdoor seating. The sun sets behind the house, casting warm light on the structure, which is surrounded by trees.
Guest suite in Edlesborough
4.96 out of 5 average rating, 155 reviews

Self-contained annexe in the Chiltern Hills

Nestled in the heart of the Chiltern Hills, Applewood Cottage offers the perfect retreat for those looking to explore the surrounding areas of outstanding natural beauty. The house and it's surrounding areas are well situated for visiting cyclists, walkers and families who want a rural escape. Although the annexe has one bedroom, we can accommodate babies and small children. Please simply ask when booking. Pub in local village. A short drive to the Ashridge Estate and Whipsnade Zoo.

Guest favorite
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 favorite
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 Little Missenden
4.97 out of 5 average rating, 230 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.

Popular amenities for Penn Street vacation rentals

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