Holiday rentals in Chesham

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Top-rated holiday rentals in Chesham

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Guest favourite
A rustic treehouse is elevated among leafy trees, connected by a wooden staircase. Surrounding foliage creates a serene environment, while a shaded area beneath features a bench and a fire pit. The natural setting offers a sense of privacy and tranquility.
Treehouse in Hertfordshire
4.96 out of 5 average rating, 259 reviews

Tree House - Hot Tub on balcony

Our rustic Glamping Treehouse stands 5m above the ground, which is accessible via an exciting seven-meter long suspension bridge. Boasting a warm themed interior, the Treehouse offers breathtaking views over the Chess Valley, which can be seen from the balcony and through the large panoramic window. Features include a spacious king-size double bed, en-suite toilet and basin facility. The outdoor balcony is home to a shower and hot tub, the perfect spot to relax amongst the surrounding treetops!

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 in Chartridge
4.86 out of 5 average rating, 199 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

Top guest favourite
The exterior of the studio is displayed during a sunset, with a warm pink sky glowing above. A conservatory with large windows is visible, surrounded by a lush garden featuring blooming flowers and green grass. The countryside backdrop includes distant trees and open fields.
Home in Amersham
4.85 out of 5 average rating, 186 reviews

Stunning riverside house in the heart of Chilterns

Breathtaking location set in the heart of stunning Chilterns countryside only 30 min from London. Come & recharge with views of the River Chess flowing past your bedroom. Relax in the large sitting/dining room (dbl sofa bed) or bask in the sunny conservatory watching swans glide by. Glorious walking on Chess Valley Walk. Nearby Amersham, Chalfont & Chenies all offer superb restaurants/shops & Met line tube. Amazing location just off M25 - Harry Potter World 15min, Heathrow 25min & Ascot 45 min.

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 in Amersham
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.

Guest favourite
The exterior of a self-contained suite is depicted, featuring a dark wooden facade with a pitched roof. A simple entrance door is framed by greenery, including shrubs and small plants that line the pathway. The surrounding lawn is well-maintained, creating an inviting approach.
Guest suite in Little Missenden
4.95 out of 5 average rating, 347 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 in Sarratt
5 out of 5 average rating, 266 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
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 Chartridge
4.98 out of 5 average rating, 112 reviews

The Nest, a cosy, stylish annex loft

Kick back and relax in this quiet, stylish, recently refurbished, self-contained studio. Well-equipped and environmentally friendly, this 1st-floor annex is situated in the Chiltern village of Bellingdon, just 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 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 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 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 favourite
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 favourite
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.

Guest favourite
A cozy kitchenette area is visible, featuring light grey cabinetry and a wooden countertop. A microwave and a kettle are positioned on the counter, while open shelving displays glassware. A small dining table is situated nearby, surrounded by a green sofa adorned with colorful cushions.
Cabin in Buckinghamshire
4.86 out of 5 average rating, 102 reviews

Cute Cabin Chesham Old Town

Cosy newly converted character annexe in the heart of the Chilterns. Just a 10 minute walk (google maps speed) to the Metropolitan underground station taking 40 minutes direct to central London. Opposite a lovely pub with Thai kitchen, a 3 minute walk in to Chesham town centre full of cafes, shops and bars. 1 king sized doubled bedroom, with en-suite shower & WC and a double sofa bed in the lounge.

Popular amenities for Chesham holiday rentals

When is the best time to visit Chesham?

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Frequently Asked Questions

  • Are there family-friendly house rentals in Chesham?

    Chesham has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Chesham?

    Experience the best of Chesham with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Chesham?

    Four-legged friends are welcome in Chesham. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Chesham?

    Yes! Work meets play with ease at over 10 house rentals in Chesham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Chesham?

    Make yourself at home in Chesham by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Asheridge, over 100 vacation rentals in Chartridge, and over 60 vacation rentals in Chesham.

  • Do house rentals in Chesham have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Chesham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesham have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Chesham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesham have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Chesham. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Chesham

  • Total holiday rentals

    Explore 30 holiday rentals in Chesham

  • Nightly prices starting at

    Chesham holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,570 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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