Vacation rentals in Chesham

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Top-rated vacation rentals in Chesham

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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 Buckinghamshire
4.86 out of 5 average rating, 239 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
The spacious open-plan living room features large windows framing views of the surrounding greenery. A comfortable seating arrangement includes two sofas and a central coffee table. A decorative ladder leads to the mezzanine, which accommodates a King size bed. Soft lighting enhances the cabin's inviting feel.
Cabin in Potten End
4.96 out of 5 average rating, 1,686 reviews

Romantic Oak Cabin Berkhamsted

This cosy luxurious self contained oak framed cabin offers the perfect peaceful setting for a relaxing getaway. Listen out and you may hear the owls at night. Backing onto the National Trust Ashridge Forest, perfect for outdoor lovers yet equally suitable for a romantic night in. 1.5 miles away, the popular market town of Berkhamsted, offering atmospheric pubs and bars for a special night out. The cabin offers cozy spacious living with King size bed on a mezzanine floor! STRICT NO PET POLICY!

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 Buckinghamshire
4.98 out of 5 average rating, 133 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 favorite
Barn in Berkhamsted
4.98 out of 5 average rating, 391 reviews

The Stables in Historic Berkhamsted

Welcome to one of the most historic parts of Berkhamsted - the hilltop site of Old Berkhamsted Place, and the original Grade 2* listed barn which remains, reputedly, the largest medieval barn in the counties of Beds, Bucks & Herts. The Stables is a spotlessly chic cottage for 2 with large gardens & parking, offering luxury linen & towels, wi-fi & TV. Ideal town/country position - 10mins walk to town centre with cafes, restos, boutiques and antique stores, and train to London is only 35mins!

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, 267 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 favorite
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 in Amersham
4.99 out of 5 average rating, 135 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 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
4.98 out of 5 average rating, 161 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
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 in Bellingdon
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 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
4.97 out of 5 average rating, 240 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.

Top guest favorite
A cozy corner of the apartment features a decorative fireplace with an ornate mantle. Handwritten notes are displayed above the mantle, and a wooden desk is positioned nearby. A vintage chair and a chandelier add to the room's charm, with warm light filtering through a window.
Condo in Hertfordshire
4.98 out of 5 average rating, 175 reviews

Wizards Retreat - 8 Mins to HP Warner Bros Studio!

Welcome to ‘The Wizard’s Retreat’ This Airbnb is perfectly located just an 8-minute drive from Warner Bros. Studios, making it the ideal stay for fans visiting the Harry Potter Tour. There's wizard books to read, games to play & spooky potions to see! Whether it’s a spellbinding weekend with friends, a cosy couple’s getaway, or a family adventure, The Wizard’s Retreat has been designed to capture the wonder and excitement of the wizarding world for all to enjoy!

Top guest favorite
The spacious lounge features a large open fireplace with a cozy fire, surrounded by antique wooden beams. Colorful seating options are arranged around a central area, with a 65-inch TV mounted on the wall. Light streams in through tall windows, enhancing the room's inviting atmosphere.
Barn in Buckinghamshire
4.99 out of 5 average rating, 101 reviews

Ancient country barn, open fire, amazing walks

A stunning 16th Century luxury barn in the Chiltern Hills, just half a mile from the London Underground. Featuring a huge open fireplace, soaring beams and a beautifully decorated Christmas tree in winter. Sleeps 8 in comfort with modern amenities, Miele kitchen, fast Wi-Fi and acres of orchards, gardens and woodland to explore. A unique blend of historic charm and modern comfort in a magical countryside setting.

Guest favorite
The exterior of the barn showcases a charming dark wood facade, complemented by large windows. A picnic table is positioned on the grassy area, surrounded by flower beds and greenery. The structure is set against a clear blue sky, suggesting a spacious and inviting atmosphere.
Home in Buckinghamshire
4.95 out of 5 average rating, 331 reviews

The Olde Dairy renovated barn

The Olde Dairy is a newly renovated barn which is very spacious and has a very cosy ambience. Popular with visitors to Warner Brothers Studios ‘ Harry Potter’ Bekonscot model village, Roald Dahl museum, Chiltern Open Air museum, Bovingdon Studios, Legoland, Windsor, and the train station 5 mins away straight into London Baker Street approximately 40mins, there are many lovely local pubs and walks on our doorstep.

Popular amenities for Chesham vacation rentals

When is the best time to visit Chesham?

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Avg. priceﺩ.ﺇ437ﺩ.ﺇ367ﺩ.ﺇ375ﺩ.ﺇ400ﺩ.ﺇ389ﺩ.ﺇ415ﺩ.ﺇ419ﺩ.ﺇ389ﺩ.ﺇ382ﺩ.ﺇ345ﺩ.ﺇ331ﺩ.ﺇ459
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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 vacation rentals in Chesham

  • Total vacation rentals

    Explore 40 vacation rentals in Chesham

  • Nightly prices starting at

    Chesham vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 2,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chesham vacation rentals include wi-fi 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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