
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.

Escape in contemporary bohemian loft style
Our cool and comfortable loft-style apartment designed by the interior company Norsonn offers the most magnificent living space, It has a truly romantic feeling and unrivalled views across the old roofs. The apartment is centrally located on the High st facing the back, so It is a very quiet and exclusive private escape. Enjoy a gourmet kitchen under the roof. Including a large bedroom on the mezzanine floor. Fully fitted kitchen, lounge area. Bathtub, TV/dvd, wifi 72 MB down/15MB Up,+ 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!

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.

Beautiful cosy Scandi-barn in Chiltern market town
A beautiful, calm and cosy space designed to feel like a home from home. Lovingly updated and modernised, whilst retaining original character and features to create a unique guest experience. Uber-clean and free from clutter, everything looks & feels fresh for each stay. The kitchen, carpets, paintwork, doors, windows and VELUX roof-lights have been replaced or updated recently. Located with a parking space in a secure, gated courtyard just moments from the town centre of Princes Risborough.

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.

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.

Elegant Countryside Cottage near Oxford
Spacious and beautifully finished countryside cottage in the heart of Brill village with views across the village green and just a 2 min walk from The Pointer pub. The perfect base for exploring the countryside, Oxford, Thame and Bicester Village. Blenheim Palace, Waddesdon Manor, the Cotswolds, Silverstone race track and London are all within easy reach. Well behaved dogs over 2 years old welcome! * Host My House manages this property which is owned by Christopher & Gillian Scott-Mackirdy *

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!

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.
Popular amenities for Chesham vacation rentals
Other great vacation rentals in Chesham

The Barn at Goring Heath

Penthouse in Putney.

Perfectly Positioned Hambleden House

Charming Coach House

Charming Victorian Cottage in Battersea

Basketmakers Cottage

Tonwell Water Tower

Modern 3 Bed | ContractorFriendly | WiFi & Parking
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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