Vacation rentals in Chesham

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Top-rated vacation rentals in Chesham

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Guest favorite

Guest suite in Amersham

4.96 out of 5 average rating, 306 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.

Dec 6 – 13

$98 per night

Guest favorite

Cottage in Buckinghamshire

4.87 out of 5 average rating, 158 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.

Jan 4 – 11

$103 per night

Guest favorite

Cabin in Buckinghamshire

4.98 out of 5 average rating, 165 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.

May 26 – 31

$296 per night

Guest favorite

Barn in Buckinghamshire

4.96 out of 5 average rating, 216 reviews

Beautiful cosy Dinky 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.

Sep 14 – 21

$146 per night

Guest favorite

Guest suite in Buckinghamshire

4.94 out of 5 average rating, 213 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.

Nov 24 – Dec 1

$81 per night

Guest favorite

Apartment in Berkhamsted

4.98 out of 5 average rating, 218 reviews

The Car House, Berkhamsted

Light and airy contemporary self contained apartment with all the facilities you would expect including parking. Located in a quiet area of Berkhamsted within walking distance of the town centre, golf course and railway station (35 minutes to Euston). Beautiful bathroom/wet room with robes and toiletries supplied. Bread, cereals, preserves, milk, tea and coffee are supplied for breakfast. If you need quiet time in the evenings to study, unwind or just chill out you will find it here.

Mar 14 – 21

$104 per night

Guest favorite

Cabin in Potten End

4.96 out of 5 average rating, 1346 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.

Sep 9 – 16

$161 per night

Guest favorite

Barn in Buckinghamshire

4.96 out of 5 average rating, 137 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.

Nov 8 – 15

$95 per night

Guest favorite

Guest suite in Chipperfield

4.95 out of 5 average rating, 358 reviews

Southcot Chalet

Garden Chalet, peaceful self contained Chalet set behind our house in Chipperfield. Large self contained double room with ensuite set in 2 acres of garden You have your own front door so can come and go as you wish. We will respect your privacy. There is a bistro table at the front and bench at the back. Teas , coffee, continental breakfast all left for you A 15 minutes walk to the village, pubs, cafe and shop. Close to train stations in to London ( 30 mins)

Mar 5 – 12

$97 per night

Superhost

Guesthouse in Buckinghamshire

4.87 out of 5 average rating, 132 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.

Dec 7 – 14

$106 per night

Guest favorite

Guest suite in Buckinghamshire

4.96 out of 5 average rating, 106 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.

Oct 6 – 13

$106 per night

Guest favorite

Home in Berkhamsted

4.99 out of 5 average rating, 216 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

Jun 27 – Jul 4

$112 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chesham's top sights

The Elgiva Theatre4 locals recommend

The Queen's Head17 locals recommend

The Black Horse Inn5 locals recommend

The Drawingroom4 locals recommend

Papad restaurant3 locals recommend

Chesham Moor Gym & Swim3 locals recommend

Other great vacation rentals in Chesham

Guest favorite

Guest suite in Hertfordshire

4.93 out of 5 average rating, 202 reviews

Beautiful rural setting a short walk from town

Feb 4 – 11

$102 per night

Guest favorite

Guesthouse in Northchurch

4.84 out of 5 average rating, 223 reviews

The Chalet at Rosemary Cottage

May 27 – Jun 3

$85 per night

Superhost

Home in Buckinghamshire

4.79 out of 5 average rating, 99 reviews

Beautiful Victorian home in Chiltern hills village

Jul 4 – 11

$225 per night

Guest favorite

Apartment in Buckinghamshire

4.88 out of 5 average rating, 185 reviews

2 Bed Flat with roof garden, central Aylesbury

Jan 1 – 8

$91 per night

Guest favorite

Casa particular in Wendover, Buckinghamshire

4.89 out of 5 average rating, 224 reviews

The Nook at Pine View - set in Roald Dahl Country

Jun 29 – Jul 6

$88 per night

Guest favorite

Guest suite in Buckinghamshire

4.98 out of 5 average rating, 49 reviews

Secluded Amersham ensuite Barn ,with parking

Mar 1 – 8

$106 per night

Guest favorite

Guest suite in Hertfordshire

5.0 out of 5 average rating, 43 reviews

Gorgeous self-contained studio in Hertfordshire

Jun 29 – Jul 6

$98 per night

Guest favorite

Cottage in Chartridge

4.83 out of 5 average rating, 59 reviews

The Stables

Jun 8 – 15

$104 per night

Show all

Quick stats about vacation rentals in Chesham

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
$10 before taxes and fees

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 20 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, 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 10 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.

Vacation rentals in Chesham

Top-rated vacation rentals in Chesham

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Chesham vacation rentals

Stay near Chesham's top sights

Other great vacation rentals in Chesham

Guest suite in Hertfordshire

Guesthouse in Northchurch

Home in Buckinghamshire

Apartment in Buckinghamshire

Casa particular in Wendover, Buckinghamshire

Guest suite in Buckinghamshire

Guest suite in Hertfordshire

Cottage in Chartridge

Quick stats about vacation rentals in Chesham

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What are the most popular amenities for House Rentals in Chesham?

Do house rentals in Chesham have a kitchen?

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

Do house rentals in Chesham have wifi?

Are there vacation rentals with a dedicated workspace in Chesham?

Where should I stay in Chesham?

Are there family-friendly vacation rentals in Chesham?

Do house rentals in Chesham have free parking?

Destinations to explore