Vacation rentals in Penn Street

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Top-rated vacation rentals in Penn Street

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Top guest favorite
Home in Wendover
5 out of 5 average rating, 47 reviews

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).

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, 255 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 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, 143 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.

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, 878 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
The charming Victorian Lodge features a classic brick exterior with white trim, framed by lush greenery. Two inviting front windows and a central doorway are surrounded by decorative flower pots. A gravel pathway leads to the entrance, highlighted by an expansive tree nearby.
Cottage in Old Windsor
4.99 out of 5 average rating, 108 reviews

Gorgeous CountryCottage overlooking Windsor Castle

The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

Top guest favorite
Guest suite in Buckinghamshire
4.96 out of 5 average rating, 384 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.

Top guest favorite
A serene scene showcases a cottage surrounded by lush greenery and a private lake. Two swans glide across the calm water, while the cottage, with its wooden facade and sloped roof, is nestled among the trees, offering a peaceful retreat in nature.
Cottage in Sarratt
5 out of 5 average rating, 280 reviews

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.

Guest favorite
An open-plan living area is presented with a leather sofa and a vibrant area rug. A modern kitchen features blue cabinetry and a breakfast bar with two stools. Exposed oak beams add character to the ceiling, and natural light fills the space through the window.
Condo in Amersham
4.97 out of 5 average rating, 67 reviews

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.

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, 174 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 Holmer Green
4.98 out of 5 average rating, 282 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.

Guest favorite
The exterior of a charming cottage is shown, featuring a combination of black wood and white walls. A welcoming entrance is highlighted, with a small bench and neatly arranged flower pots along the stone pathway leading to the door. A clear blue sky is visible above.
Home in Buckinghamshire
4.87 out of 5 average rating, 15 reviews

Tranquil Chilterns Farm Hideaway

Kick back and relax in this calm, stylish space. Nestled on a farm within the rolling hills of the Chilterns AONB, this is an ideal spot for those seeking a peaceful short stay, with all the amenities of a village nearby including the Chilterns Railway which will take you into London within 40 minutes. The cottage is immaculate and completely self-contained with utility room, full kitchen, private bathroom, and open plan lounge and king bedroom overlooking the countryside.

Guest favorite
Cabin in Chorleywood
4.96 out of 5 average rating, 124 reviews

Hagrid Hut Themed - Hot Tub - Warner Bro Studio

Hagrid & Fang are away and would like you to watch over his home, located next to the Forbidden Forest! This unique Glamping experience is conveniently located only 12 minuets drive from the Warner bros Studio Tour & 40 minuets to central London via Chorleywood Metropolitan line. Hagrid's Hut sleeps five wizards - making it the perfect accommodation choice for families and friends. Soak under the stars in the leaky cauldron wood fired hot tub nestled in nature, MAGIC.

Popular amenities for Penn Street vacation rentals