Vacation rentals in Penn Street

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Top-rated vacation rentals in Penn Street

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Top guest favorite
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, 393 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.

LocationFamilyNearby

Superhost
Bungalow in Amersham
4.86 out of 5 average rating, 257 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.

ValueFamilyNearby

Top guest favorite
An open plan living area is showcased with a dark sofa, light wooden coffee table, and a small round dining table. A floral wall hanging is displayed above the sofa, while natural light enters through a skylight, illuminating the neutral-colored walls.
Guest suite in Amersham
4.98 out of 5 average rating, 144 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.

LocationFamilyAccess

Guest favorite
A spacious, open-plan living area features a comfortable sofa and a coffee table, with natural light pouring in through skylights. Large glass doors lead to an outdoor dining area, creating a seamless connection between indoor and outdoor spaces.
Home in Holmer Green
4.97 out of 5 average rating, 39 reviews

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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Top guest favorite
Guest suite in Buckinghamshire
4.96 out of 5 average rating, 386 reviews

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.

ValueLocationOutdoor spaces

Top guest favorite
The charming cottage features traditional brickwork and a steeply pitched roof. A well-maintained garden showcases vibrant lavender and lush green grass. Decorative flowering plants enhance the inviting entrance, framed by an archway of climbing greenery and detailed, patterned windows.
Cottage in Beaconsfield
5.0 out of 5 average rating, 24 reviews

Beautiful English Cottage

A unique, luxury, 5 bedroom, English cottage, in the Chilterns. Walking distance to town/train/shops/pub and 30 mins by train into London. Open plan downstairs living with huge open fireplace and a chefs dream kitchen. All rooms ensuite, with Egyptian cotton sheets and fluffy towels. Beautiful enclosed gardens, with BBQ hut and pretty summer house, and huge outside table, complete with cushions, perfect for dining. Herb garden and fruit trees to the rear. Large front drive for parking.

LocationFamilyGetting around

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, 175 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.

LocationValueShared spaces

Top guest favorite
An open plan living space features a wooden dining table with bench seating, positioned next to a cozy lounge area. A comfortable brown leather sofa and natural light from an adjacent window create a welcoming atmosphere. Artwork adorns the wall, enhancing the modern decor.
Guest suite in Hertfordshire
5.0 out of 5 average rating, 103 reviews

Gorgeous self-contained studio in Hertfordshire

Come and enjoy our unique self-contained Studio attached to our house. It is a quiet and peaceful spot, ideal for rest and recuperation or to explore the surrounding rural areas and Chilterns AONB. It is a fully self-contained basement apartment, its open plan with a lounge area, dining area, bedroom with its own en suite shower room. It has its own entrance way down a terraced flower bed, and has a small private patio with table and chairs which is yours to use at your leisure.

LocationValueCondition

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.
Place to stay in Holmer Green
4.98 out of 5 average rating, 287 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.

ValueFamilyBreakfast

Guest favorite
Home in Beaconsfield
4.91 out of 5 average rating, 244 reviews

18th century cottage

Self contained character annex in the beautiful Buckinghamshire countryside. Low ceilings and a narrow steep staircase with handrail and stairgates top and bottom. Parking spaces at the front and use of garden to the rear. Fantastic location on the edge of the Chilterns; good road and rail links to London, Oxford and Wembley. Close to the Thames, Windsor, Marlow, Cliveden, Hedsor House, Harry Potter Studios and Legoland. Plus there’s a pub next door!

FamilyLocationParking

Top guest favorite
A sweeping gravel drive leads through well-maintained gardens featuring vibrant greenery, orderly hedges, and various shrubs. The landscape includes a mix of trees and colorful plant beds, creating a serene outdoor environment ideal for leisurely walks.
Bungalow in Amersham
4.99 out of 5 average rating, 72 reviews

Beautiful, spacious lodge, lovely gardens

A beautiful, spacious 1750 sq ft lodge set in over 6 acres of lovely and tranquil gardens, yet within walking distance of Little Chalfont's shops, restaurants, amenities and Chalfont & Latimer Underground Station, which provides easy access to London. Chalfont St Giles is a very nice area and the perfect location for walks and tours, trips with family & friends or for business - why not enjoy a relaxing stay in gorgeous surroundings?

LocationFamilyWalkability

Superhost
The 16th-century farmhouse is framed by a white gate, surrounded by verdant lawns. The stone exterior showcases intricate architectural details, with large windows and a decorative entrance. Lush trees and sparse shrubbery complete the charming landscape under a clear blue sky.
Home in Hedgerley
4.9 out of 5 average rating, 111 reviews

Slade Farmhouse with secluded Hot Tub

Check in from 16:00 and checkout is at 10:00. Experience an exquisite 16th-century farmhouse, recently renovated for up to 15 guests. The unique rooms offer a blend of textiles and colours, combining Art Deco with Country Chic style. Enjoy the inviting atmosphere, exposed beams, and Venetian mirrored furnishings. Relax in the hot tub on the terrace with stunning paddock views. Conveniently located near a charming village pub.

LocationFamilyPets

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