
Vacation rentals in Chesham
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Top-rated vacation rentals in Chesham
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The Nest, a cosy, stylish annex loft
Kick back and relax in this quiet, stylish, self contained studio. Cosy, 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, away from their home. The name is inspired by the 50+ species of bird found locally, including the Red Kites.

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

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.

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!

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.

Stag Lodges
Nestled amongst the stunning views of the Chess Valley, Stag Lodges welcomes you to experience glamping in the beautiful Hertfordshire countryside with all the comforts of your own home but in a luxury, handcrafted wooden lodge. Chorleywood is on the Met Line, allowing a short journey into London. We are also on the doorstep of Warner Bros Studio Tour and other famous attractions. Whether its a special occasion for two, planning a family adventure or time with friends, Stag Lodges is for you!

Charming 1 bedroom place with parking.
Relax in the beautiful Chilterns in a comfortable self contained suite with En-suite shower, dining area, 40" Smart TV, fridge. 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.

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.

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.

The Windmill Blackthorn Hill, Nr. Bicester Village
Featured in the 'Times Newspaper' Top 10 best Places to Stay with Spectacular Views: "A truly amazing experience." Enjoy a luxurious stay in a historic 17th c. listed windmill and create unforgettable memories. You won’t be short of things to do—enjoy boutique shopping at the renowned Bicester Village or take leisurely walks around historic Oxford, just a 15-minute train ride away. Additionally, Blenheim Palace and Waddesdon Manor are nearby attractions worth exploring.

Luxury 2 bedroom cottage
Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Cosy Victorian cottage in central Berkhamsted
Renovated beautiful cottage with open plan living on the ground floor with corner sofa and gas stove. French doors are leading out to a private courtyard garden. Well appointed kitchen with hob, oven and dishwasher. Washing machine in separate lobby leading through to a ground floor shower room / WC. Upstairs there are 2 bedrooms , a main bedroom with king-size bed and a twin room with 2 single beds. Self check in
Popular amenities for Chesham vacation rentals
Other great vacation rentals in Chesham

Bakersfield Retreat

Honey Barn - Stunning 4-Bed Rural Paradise

Chic Apartment - 2 mins to Hampton Court

The Barn at Goring Heath

Bright & Spacious Chilterns Hideaway

Victorian Townhouse in Tring

Enchanting Cottage in the heart of the Chilterns

Amazing 3bed, 30mins to London, H Potter Studios
When is the best time to visit Chesham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ437 | ﺩ.ﺇ367 | ﺩ.ﺇ375 | ﺩ.ﺇ400 | ﺩ.ﺇ389 | ﺩ.ﺇ415 | ﺩ.ﺇ419 | ﺩ.ﺇ389 | ﺩ.ﺇ382 | ﺩ.ﺇ345 | ﺩ.ﺇ331 | ﺩ.ﺇ459 |
| Avg. temp | 4°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 14°C | 11°C | 7°C | 5°C |
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 vacation rentals in Chesham

Total vacation rentals
Explore 30 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 2,570 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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