
House holiday rentals in Chesham
Find and book unique houses on Airbnb
Top-rated house rentals in Chesham
Guests agree: these houses are highly rated for location, cleanliness and more.

Five Star Boutique House near Windsor Castle, Ascot & London
This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Magical Marlow town centre
Wing Cottage is a charming period terraced cottage with log burner in the heart of Marlow. It has been stylishly refurbished and has its own secluded courtyard garden. 5 minutes walk from High St shops with Everyman Cinema, Tom Kerridge’s Michelin* Hand &Flowers & The Coach, plus Marlow Ivy Garden, Côte Brasserie, Piccolino, The Compleat Angler and several historic pubs. The Park and Thames Path river walk are 10 minutes walk. Nearby bus stops serve neighbouring Henley-on-Thames (8 miles away).

Secluded River Thames Lodge with Spectacular Views
Herons is totally unique, a beautiful detached lodge situated on the banks of the River Thames. Beautiful interiors and the views are simply wonderful from sunrise to sunset. Herons is the perfect place to unwind and relax, just sit and watch the wildlife and the boats milling along the river. Nearby are the Thames Market towns of Wallingford, Henley and Abingdon and the beautiful surrounding countryside.The historic city of Oxford is only 8 miles away and Bicester Village is a 30 minute drive.

Pool House at Mill Cottage
The Pool House at Mill Cottage offers a unique riverside escape with exclusive access to a private pool (Mar 1st - Oct 1st 2025 & Apr 1st - Oct 1st 2026). Nestled on the Thames, enjoy easy access to riverside cafes and restaurants by foot or boat. The charming one-bedroom retreat features blackout blinds for restful nights, plus a small sofa bed for extra guests. Just minutes from Goring on Thames village and the train station, it also boasts a BBQ and outdoor seating area for relaxing evenings.

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.

The Stables, Little Marlow
A fabulous, converted barn, located in the very desirable village of Little Marlow, Bucks. The property is set within 3/4 acre for your private use and has it's own private driveway + parking. The interior has underfloor heating, a wood burning stove, panelled walls, en-suite, and a family bathroom. Little Marlow has been in numerous Midsomer Murder TV series. The village has two pubs, a cricket ground and a church. The property is a 10 min walk to the river Thames. AONB & cons. area

Countryside Retreat with hot tub
This modern country retreat features panoramic views of the Oxfordshire countryside from the open-plan kitchen, living room. Ideal for a peaceful getaway, our home offers high-speed Wi-Fi, a fully equipped kitchen, and cozy furnishings. Two bedrooms featuring superking beds, one with ensuite. Outside bbq area with comfy seating, firepit, dining area and hot tub. Whether you're here for a weekend escape or a longer stay, this house provides the perfect setting to relax and unwind.

Luxury self-contained Annexe with balcony Jacuzzi
Luxury self-contained annexe on the edge of the Chilterns, situated in the peaceful countryside which can be enjoyed from the hot tub, yet only 5 mins to the M40, 15 mins to Oxford Park & Ride & 15 mins to the station with trains to London taking 45 mins. It is the perfect place to relax with cosy lounge, wood burning stove, bespoke kitchen & underfloor heating. Upstairs features a super-king sized bed, seating area, luxury wet-room with underfloor heating, balcony and Jacuzzi.

Gorgeous Cottage in Skirmett with Parking
This gorgeous 3 bedroom cottage, is in the quiet village of Skirmett, situated in the Hambleden Valley, in a particularly pretty area of the Chilterns. Many films and TV series have been filmed in the area, as it is often thought of as quintessentially English. Just a hop and a skip from London and its airports and a short distance from Marlow, Henley or High Wycombe stations... come and step back in time and enjoy a rural setting you won't forget.

Chiltern Retreat | Walks, Work & Free Parking
Set in a peaceful rural location near Saunderton Station, this family-friendly home offers scenic countryside walks and nearby golf courses. Ideally placed for exploring Coombe Hill, Chequers, Waddesdon Manor, the Hellfire Caves and the Roald Dahl Museum, all just a short drive away. The house features a fully equipped kitchen, 65-inch TV, utility room and downstairs bathroom, providing comfort, space and everything needed for a relaxing stay.

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

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.
Popular amenities for house rentals in Chesham
House rentals with a pool

The Mill House

Spacious Home Heated Pool(April-Sep) in Tilehurst

Kensington Pool & Piano | Unique 3BR w/ Central AC

Wellness Escape by River: Sauna, Pool, Hot Tub

Stunning hideaway house

Old Wharf Cottage

3 miles to Royal Ascot, pool, sleeps 12 in 2 acres

South Wing of Country House
Weekly house rentals

Cozy Corner

Racecourse Marina Lodge | Hot tub | Parking | EV

Stunning Edwardian Family Home in the Chilterns

The Cosy Cottage. in Old Soles bridge Lane

The Wild Bloom- 3 bed with parking

Cozy 3bed 30 mins to London & H Potter Studios

Cosy, Convenient Cottage in central Marlow

Tonwell Water Tower
Private house rentals

Calm spacious home w/ large terrace & free parking

Modern Country House

The Heights

High end luxury home with Hot Tub | Parking, EV

Big Group Stay in Harrow•3 Parking•Game Room

Home in Marlow

Stylish self-contained 1-bedroom

Enchanting Cottage in the heart of the Chilterns
Quick stats about house rentals in Chesham

Total holiday rentals
Explore 20 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 1,350 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 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!
Destinations to explore
- Paddington
- Covent Garden
- St Pancras International
- British Museum
- Hampstead Heath
- The O2
- Buckingham Palace
- Wembley Stadium
- Tower Bridge
- Marble Arch
- Tottenham Court Road
- London Bridge
- Big Ben
- Trafalgar Square
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events
- Borough Market
- Clapham Common
- Brockwell Park
- University of Oxford





