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Vacation rentals in Chesham

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Top-rated vacation rentals in Chesham

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

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Guest suite in Amersham

4.96 out of 5 average rating, 317 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.

Cabin in Buckinghamshire

4.98 out of 5 average rating, 188 reviews

Romantic hot tub and private heated pool retreat

THE POOL IS 90 DEGREES F! The retreat cabin is a place for couples to genuinely switch off from the outside world. Relax in private luxury with a fantastic heated teak hot tub and award winning luxury swimming pool just feet from your door. Fitted with double aspect doors in which each panel has integral remote controlled privacy blinds which can be fully or partially opened and tilted. The outside area has a sensational sound system. The cabin has both air conditioning and underfloor heating.

Guest suite in Hertfordshire

4.93 out of 5 average rating, 218 reviews

Beautiful rural setting a short walk from town

Delightful 1-bedroom detached annex in the grounds of an 1895 Rothschild house. Situated in the historic conservation area of Tring, the property has beautiful views of Tring Park and is situated a few minutes' walk from the town centre, restaurants and bars. Only 1 mile from Tring station. Trains run 3 times an hour, direct to Euston in 40 minutes. Perfectly situated for Tring Park School, Tring Natural History Museum, Ashridge Estate, the Ridgeway, Harry Potter, Whipsnade Zoo, the Chilterns.

Barn in Buckinghamshire

4.96 out of 5 average rating, 231 reviews

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.

Barn in Berkhamsted

4.98 out of 5 average rating, 328 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!

Guest suite in Buckinghamshire

4.95 out of 5 average rating, 240 reviews

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.

Cabin in Potten End

4.96 out of 5 average rating, 1,396 reviews

Romantic Oak Cabin Berkhamsted

This cosy luxurious self contained oak frame 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, this is perfect for outdoor lovers but equally suitable for a romantic night in. 1.5 miles down the road, the popular market town of Berkhamsted is offering atmospheric pubs and bars for a special treat out. The cabin offers comfortable, spacious living with King size bed.

Barn in Buckinghamshire

4.96 out of 5 average rating, 141 reviews

Fantastic s/c barn in "secret" Chiltern valley

Fantastic self-contained spacious accommodation which forms part of a Grade II listed barn conversion tucked away in a beautiful hidden Chiltern valley; perfect for walking and cycling from the doorstep but also only four miles from both Berkhamsted and Chesham stations with easy access to London. The accommodation comprises of four good-sized, newly decorated rooms, all closed off from the owners who live in the other part of the barn but who are on hand should you need them.

Rental unit in Buckinghamshire

4.87 out of 5 average rating, 157 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, 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.

Guesthouse in Buckinghamshire

4.87 out of 5 average rating, 135 reviews

The Old Hay Barn, Ashley Green

Our rustic Victorian barn in located in the heart of Ashley Green village, a short drive to both historical Berkhamsted or Chesham high streets and train stations. Delightfully converted to a charming, private one-bedroom residence, it is fully furnished to a high standard. The barn has access to its own private garden and parking space. Its warm and authentic feel makes it ideal for a getaway, mini country break or a relaxing space during the working week.

Guest suite in Buckinghamshire

4.96 out of 5 average rating, 111 reviews

Private Annex for two guests (+) in Chess Valley

Relax, rejuvenate in your own Chiltern retreat whilst being only 35 minutes by train to London. Located in an AONB in the Chess valley you can from your private entrance enjoy walking, cycling, bird watching and sight seeing. The sitting room opens onto the comfortable double bedroom with an en suite shower room. The Garden room, bedroom and bathroom are separated from the rest of the house Beverages, breakfast pack, towels and toiletries. are provided.

Home in Berkhamsted

4.99 out of 5 average rating, 227 reviews

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

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Popular amenities for Chesham vacation rentals

Free parking on premises

Air conditioning

Stay near Chesham's top sights

The Black Horse Inn5 locals recommend

The Elgiva Theatre4 locals recommend

The Queen's Head17 locals recommend

The Drawingroom4 locals recommend

Papad restaurant3 locals recommend

Chesham Moor Gym & Swim3 locals recommend

Other great vacation rentals in Chesham

Cottage in Buckinghamshire

4.89 out of 5 average rating, 111 reviews

The Cottage in Old Amersham

Place to stay in Buckinghamshire

4.78 out of 5 average rating, 18 reviews

Brand new studio apartment

Rental unit in Ashley Green

5 out of 5 average rating, 15 reviews

The Studio, self contained accom

Guest suite in Buckinghamshire

4.98 out of 5 average rating, 53 reviews

Secluded Amersham ensuite Barn ,with parking

Guest suite in Hertfordshire

5 out of 5 average rating, 52 reviews

Gorgeous self-contained studio in Hertfordshire

Guest suite in Amersham

4.99 out of 5 average rating, 76 reviews

Renearth - Private, modern double bed studio apt.

Home in Buckinghamshire

4.98 out of 5 average rating, 61 reviews

Detached modern home with stunning views

Cottage in Lee Common

4.96 out of 5 average rating, 25 reviews

Tawny's at Willow Barn

Quick stats about vacation rentals in Chesham

Total rentals
40 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for House Rentals in Chesham?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 20 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
How much does it cost to stay in house rentals in Chesham?
Experience the best of Chesham with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
Are there vacation rentals with a dedicated workspace in Chesham?
Yes! Work meets play with ease at over 20 vacation 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, and over 60 vacation rentals in Chesham.
Are there family-friendly vacation rentals in Chesham?
Chesham has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.

Destinations to explore