
Holiday houses in Upper Winchendon
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Top-rated holiday rentals in Upper Winchendon
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Escape to Country Living at its Finest!
Escape to the country and unwind at this charming, elegant cottage in 2 acres of lovely gardens with swimming pool, tennis badminton and table tennis, and county walks starting from your door. Located on the edge of the award winning village of Cuddington, walk to the thatched roof pub for drinks and dinner or village store for supplies and news papers. Only 10 minutes drive to the bustling market town of Thame, 35 minutes to Oxford, 40 minutes to London by train and 45 minutes to London LHR.

The Little Barn -beautiful country getaway
The Little Barn is set in one and a half acres of paddock in beautiful countryside near National Trust jewel-Waddesdon Manor. A stylish two bedroom barn - perfect for a tranquil getaway. Near the historic village of Quainton, with its pub on the green, village shop and windmill, there are many rural walks or enjoy our paddock with small orchard and bee hives. The Little Barn is ideal for 2 couples or a family. As well as 2 bedrooms , there is a sofabed in the living room and single trestle bed.

The Annex
Set in the hills of Bucks enjoying arguably the finest views in the area is The Annex. The Annex is new for 2025, having been extensively refurbished to the highest standards. Guests will enjoy exclusive use of the annex with its private patio area and private hot tub. You will also benefit from private use of the swimming pool every other day of your stay. With a large living area, two ensuite bedrooms and well equipped kitchen The Annex is the perfect rural retreat for couples and families.

Modern Self-Contained Detached Studio in Village
The Studio is a modern, self-contained and stylish space with king sized bed and fully fitted kitchen. Detached space with secure WiFi, off-road sheltered parking & private entrance, perfect for self-catered stays and business trips. Situated in a picturesque village backing onto open fields and a short walk from The Crown pub. Just 2 miles from Haddenham & Thame train station (direct links to Oxford & London), 15 minutes from M40 motorway & 4 miles north of Thame. Not suitable for infants.

"The Annexe" modern self-contained detached studio
Modern detached studio set on an equestrian property, on the outskirts of the beautiful Buckinghamshire village of Quainton. Quainton offers wonderful walks and views, a working Windmill, a delicious cafe, a shop and a friendly pub - perfect for that much needed getaway. Whether you are staying for business or time off, there are plenty of lovely restaurants and pubs to visit locally. Convenient location for Bucks Railway centre, Waddesdon, Bicester and within 30min of Silverstone and MK Bowl.

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 *

Historic Manor Stables - Chilterns Hideaway
A stunning converted stable from the 1700s, set in the picturesque village of Brill, Buckinghamshire, known for its restored windmill. This spacious hideaway, retaining original stable dividers, exudes charm with an inviting, open layout. Inside, find a cosy living room, reading room, dining area, large kitchen, and laundry room with washer and dryer. The property offers three bedrooms sleeping six: two singles, one double, and a king bed. Enjoy full access to a private garden and parking.

The Woodland Retreat With Private Hot Tub Spa
Our brand new listing is a truly unique woodland retreat with a luxury super king bed, dedicated private hot tub & 65 inch tv. Perfect for a couple get-away, this place will take your breath away. Nestled in our remote private woodland on our farm estate this little gem is in touch with nature yet fully fitted with all the home comforts you need. Additionally the woodland retreat includes: 1x private bathroom, a fully fitted outdoor kitchen, WiFi and a bespoke oak outdoor dining table.

Annexe in the heart of Haddenham
1 bed self-contained annexe with bathroom and kitchen overlooking our beautiful garden, situated in a former farmhouse in the heart of Haddenham. Bright and airy, the annexe is brilliantly located in the historic part of the village, lovely local pubs and the award winning Norsk cafe are just a short walk away. Just a 10 minute walk from Haddenham mainline train station giving easy access London (40 mins) and Oxford (25 mins). Direct trains to Bicester Village take just 14 minutes.

Couples & Business Country Retreat 5*
Tucked away for privacy & calm The Lodge is a beautifully designed escape created with couples in mind & business travellers. At its heart is a sumptuous king-size four poster bed, dressed in soft linens for an indulgent boutique-hotel feel, flowing elegantly into a stylish living,dining & kitchen area, thoughtfully equipped for relaxed stays. Bi-fold doors open onto your own private garden for dining or relaxing al-fresco. Elegant walk-in shower room. Escape the World.

Coach House in rural setting.
The Coach House is a self-contained building with ample parking at the end of a no-through road and surrounded by the Grade I Waddesdon Estate. Waddesdon Manor (NT) is in walking distance, Bicester Village is within easy reach and walks abound. The open-plan ground floor has spacious seating and dining and kitchen areas. The cosy beamed attic contains the bedroom, landing-com-study/dressing area and wet room/bathroom. Sleeps two upstairs in the bedroom.

Cosy village apartment near Waddesdon Manor
Welcome to our cosy 2 bedroom flat located in the charming village of Waddesdon! Perfectly situated for a peaceful retreat, our flat is ideal for couples, friends, or small families looking to explore the stunning Buckinghamshire countryside. Our flat is conveniently located within walking distance to local shops, pubs, and restaurants, as well as the picturesque Waddesdon Manor. We look forward to welcoming you to our lovely flat in Waddesdon!
Popular amenities for Upper Winchendon holiday rentals
Other great holiday rentals in Upper Winchendon

Cheerful 3 bedroom property set in the countryside

The Bee Hive

Foxglove Barn - Rural Escape - 3 Bed

Completely refurbished cottage in heart of village

Beautiful 3Bd Village Home Walk to Waddesdon Manor

Modern Summer House | Private & Self-Contained

6BR|Sleeps 13|Contractor|Garden|WiFi|Parking

The Aylesbury Family Retreat Home with Parking
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- The O2
- ExCeL London
- Tower Bridge
- Silverstone Circuit
- Emirates Stadium
- Tottenham Hotspur Stadium
- Cotswolds AONB
- Clapham Common
- University of Oxford
- Thorpe Park Resort
- Victoria Park
- The National Bowl
- Blenheim Palace
- Buckingham Palace
- Big Ben
- Alexandra Palace
- London Eye





