
Vacation rentals in Penn Street
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Top-rated vacation rentals in Penn Street
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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.
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Serene & Private Annexe in Village Centre
Set in the heart of the bustling village of Wendover, nestled behind the historic Lime Tree House, this self-contained Annexe is perfect for short or long stays; spacious, well equipped and peaceful, with a private large walled garden. It offers the best of all worlds; a countryside escape surrounded by the stunning Chiltern Hills and Wendover Woods, a central location with an array of Pubs, eateries and shops on the doorstep , plus easy access to London (station 2 mins walk/Marylebone 45 mins).
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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.
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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.
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Modern6bed, 30min Airport,London Legoland Windsor
Family friendly Chiltern Hills AONB Parking for 4/5 cars Brand new appliances, John Lewis bedding mattresses Large open plan kitchen, dining/living space+75"smart TV Underfloor heating groundfloor Ground floor en-suite, walk in power shower, zip-link super king bed Upstairs king bed, ensuite Smart TV upstair bedrooms Downstair toilet Large movie/game room Close to woodland London, Oxford, Heathrow, Windsor Castle, Legoland, Roald Dahl Museum,Bekonskot Model Village, Hughenden Manor, train
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Charming 1 bedroom place with parking.
Relax in the Chilterns in a comfortable self contained suite with En-suite shower, dining area, 42" Smart TV, fridge and microwave. 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.
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Crestyl Cottage riverside barn for 2 with hot tub
Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.
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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.
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Stylish Character Home | Old Amersham Market Town
In the heart of the historic market town of Old Amersham, dating back to 1580 is the boutique, recently (2021) renovated and period Hops Cottage (given its name from the old hop house and brewery next door). The flat is on the first floor with large vaulted living area with mezzanine, full of light with windows on two sides and in the roof. The property still retains period features including original oak beams. Converted with luxury and comfort in mind, its makes for a memorable stay.
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The Woodland Retreat With Private Hot Tub Spa
Our brand new listing is a truly unique woodland retreat with a luxury super king bed, dedicated private hot tub & 65 inch tv. Perfect for a couple get-away, this place will take your breath away. Nestled in our remote private woodland on our farm estate this little gem is in touch with nature yet fully fitted with all the home comforts you need. Additionally the woodland retreat includes: 1x private bathroom, a fully fitted outdoor kitchen, WiFi and a bespoke oak outdoor dining table.
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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.
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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.
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Popular amenities for Penn Street vacation rentals
Other great vacation rentals in Penn Street

Stylish newly renovated Two bedroom apartment
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Lovely home in Little Chalfont
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The Potting Shed
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Olcote by Fullards
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The Wild Bloom- 3 bed with parking
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Beautiful, spacious lodge, lovely gardens
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Cosy Country Cottage
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Charming Country Cottage with Lovely Views
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Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- The O2
- Emirates Stadium
- Tower Bridge
- Silverstone Circuit
- Tottenham Hotspur Stadium
- Clapham Common
- Thorpe Park Resort
- South Downs National Park
- Blenheim Palace
- Buckingham Palace
- Victoria Park
- Alexandra Palace
- London Stadium
- Big Ben
- The National Bowl
- London Eye
- Windsor Castle





