Holiday rentals in Chesham

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Top-rated holiday rentals in Chesham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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
4.96 out of 5 average rating, 381 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.

Guest favourite
The main room features a spacious bed with a striped comforter and decorative pillows. Two nightstands with lamps are positioned beside the bed. Large windows with dark shades provide natural light. A chair and small desk are also visible, complementing the light-colored floor.
Flat
4.87 out of 5 average rating, 201 reviews

Tiles Farm Studio - Heart of the Chilterns

Welcome & thank you for considering a stay at Tiles farm, located near Chesham in the heart of the Chilterns. Our annex provides a light & modern place to explore, relax or simply somewhere to stay for work. The annex benefits from its own private entrance, very fast broadband, parking for up to two vehicles, beautiful views of the surrounding countryside, small patio & communal gardens. There is a compact kitchen with hob, fridge & microwave/oven. There is a private bathroom with small shower

Superhost
Bungalow
4.85 out of 5 average rating, 241 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 favourite
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
4.98 out of 5 average rating, 134 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.

Top guest favourite
Barn
4.98 out of 5 average rating, 133 reviews

Ancient barn with private heated pool and 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.

Top guest favourite
Guest suite
4.95 out of 5 average rating, 353 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 favourite
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
5 out of 5 average rating, 269 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.

Top guest favourite
The entrance of the studio apartment features a charming brick façade adorned with vibrant flowers. A small wooden bench sits on a stone patio, flanked by decorative planters filled with blossoms. A white front door with glass panels invites guests into the cozy space.
Guest suite
4.99 out of 5 average rating, 137 reviews

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.

Top guest favourite
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
4.98 out of 5 average rating, 162 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 favourite
A spacious seating area features two black sofas arranged around a light wooden coffee table. Natural light filters through the large windows, enhancing the airy atmosphere. Decorative pillows add subtle texture, while a floor lamp stands nearby, contributing to the cozy environment.
Flat
4.98 out of 5 average rating, 269 reviews

Large Luxury Studio Apartment

My Studio Apartment is bright and airy perfect loft style living in the Historic Market town of Berkhamsted. The Studio is equidistant between town and country, Berkhamsted Golf Club is just over 5 mins walk away, whilst the the High St with an abundance of stylish coffee shops, boutiques & restaurants a 12 min walk. The Grand Union canal is a 10 min stroll down the hill with many canal side pubs to while away a few hours. Berkhamsted Station a 12 min walk, be in London in 30 min

Top guest favourite
A living area features a dark gray sofa adorned with decorative pillows. In front, there is a white coffee table, showcasing a collection of books and a vase of colorful flowers. A framed photograph of a bird hangs on the wall above the sofa.
Loft
4.98 out of 5 average rating, 113 reviews

The Nest, stylish, spacious, annex loft studio

Relax in this quiet, stylish, recently refurbished, fully self-contained studio. Well-equipped and environmentally friendly, this 1st-floor annex is situated in the Chiltern village of Bellingdon, North of the market town of Chesham. The perfect location for those exploring the Chilterns, designated an ‘Area of Outstanding Natural Beauty’ walking, cycling or for those working locally. The name is inspired by the 50+ species of bird found locally, including the Red Kites.

Top guest favourite
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
4.97 out of 5 average rating, 247 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 Chesham holiday rentals

When is the best time to visit Chesham?

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Avg. price£71£66£75£80£78£83£84£78£77£69£66£92
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Frequently Asked Questions

  • What are the best places to stay in Chesham?

    Stays in the historic town centre, residential neighborhoods, and near green spaces are often suggested for exploring Chesham. Many accommodations are located around Lowndes Park and close to local shops.

  • What are the best things to do in Chesham with kids?

    Families often explore Lowndes Park’s play areas, visit Chesham Museum for interactive exhibits, and join local nature trails. Seasonal events and town markets can also be engaging for children.

  • What are some of the best things to do in Chesham?

    You can explore Chesham’s market, stroll through Lowndes Park, and enjoy countryside walks on trails leading into the Chiltern Hills. Visiting artisan shops and historic pubs is frequently recommended.

  • How is the weather in Chesham?

    Chesham has cool winters around 35–45°F (2–7°C) with regular rainfall, while summer brings milder afternoons near 54–72°F (12–22°C) and occasional showers. Spring and autumn offer comfortable walking weather and changing landscapes.

  • When is the best time to visit Chesham?

    Late spring and summer are frequently suggested for visiting Chesham, with milder weather near 54–72°F (12–22°C) and blooming countryside. Autumn brings colorful foliage, while local winter events create a festive atmosphere.

  • What are the best places to visit in Chesham?

    Lowndes Park is often recommended for scenic walks, with the town’s market and Chesham Museum providing local history and culture. The Chiltern Hills nearby encourage nature exploration.

  • What are some hiking trails in Chesham?

    Chesham has access to the Chiltern Hills, with trails like the Chess Valley Walk and woodland paths starting near Lowndes Park. Locals often recommend these routes for nature and countryside views.

  • What are some family activities we can do in Chesham?

    Chesham has spaces like Lowndes Park for walks, play areas for children, and regular markets that invite families to explore together. Many enjoy picnics in the countryside or gentle trails around town. Cultural and seasonal events are often suggested for families.

  • What are some of the best day trip ideas from Chesham?

    Explore market towns around Chesham, visit nearby heritage sites, or walk scenic stretches of the Chiltern Hills. Gardens, museums, and outdoor parks in surrounding villages are frequently suggested.

  • Are there any pet friendly accommodations available in Chesham?

    Chesham has several pet-friendly accommodations, often located near parks and walking trails. Guests commonly find stays in residential areas or around Lowndes Park suitable for bringing pets.

  • What are some local tips for visiting Chesham?

    Chesham has a traditional market, many independent shops, and scenic countryside walks. Locals often suggest exploring town trails and sampling seasonal produce from farm shops around the area.

  • What is Chesham known for?

    Chesham is known for its historic market town charm, vibrant local arts scene, and access to the rolling Chiltern Hills. Its mix of green spaces, artisan shops, and heritage landmarks is frequently highlighted.

  • What are the best hidden gems to explore in Chesham?

    Explore quiet woodland paths along the River Chess, visit lesser-known local cafes, and discover small galleries or craft shops tucked in side streets. These spots reveal Chesham’s creative and natural surroundings.

  • What are the best foods to try in Chesham?

    Locally baked goods, British-style pies, and farm-sourced cheeses are often suggested in Chesham. Some cafes also serve seasonal produce and classic afternoon tea inspired by the region’s traditions.

  • What should I bring for a trip to Chesham?

    Bring layers for variable weather, including a waterproof jacket and comfortable shoes for walking trails. A reusable tote is handy for shopping at local markets or carrying picnic essentials.

  • What is the nightlife in Chesham like?

    Chesham has traditional pubs, cozy bars, and occasional live music venues centered in the town. Evening activities focus on gathering spots with locally rooted food, drinks, and performances.

  • What are the most popular events or festivals in Chesham?

    Seasonal fairs and community festivals, especially around spring and summer, are popular in Chesham. The Chesham Christmas festival and open-air performances in local parks are often highlighted.

  • Are there family friendly vacation rentals in Chesham?

    Chesham has a variety of family-friendly vacation rentals, including homes near parks, quiet neighborhoods, and around the town centre. Many options feature easy access to walking trails and playgrounds.

Quick stats about holiday rentals in Chesham

  • Total holiday rentals

    Explore 40 holiday rentals in Chesham

  • Nightly prices starting at

    Chesham holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 2,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Chesham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesham rentals

  • 4.8 Average rating

    Chesham stays are highly rated by guests – averaging 4.8 out of 5!

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