Vacation rentals in Upper Winchendon

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 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.

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.

Modern Self-Contained Detached Studio in Village

The Studio is a newly-built, 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, Birmingham & London), 15 minutes from M40 motorway and 4 miles north of Thame.

Cosy listed barn in peaceful country village.

Beautiful grade 2 listed barn conversion with unique historical features. Mezzanine king bedroom overlooking a large open vaulted ceiling living space. Set in tranquil mature gardens & situated next to the owner's cottage & the historic Saxon village church with a lovely pub serving lunch and evening meals Tues- Sun a 5 minute walk away. We are 30 mins from Bicester Village, Silverstone, Stowe House, Waddesdon Manor, Claydon House, The Ridgeway, The Chilterns, Ascott House & Bletchley Park.

Countryside Getaway - Luxurious Converted Dairy

The Dairy is a beautifully converted luxury 2 bedroom property located on Middle Farm in the Buckinghamshire countryside. An idyllic setting perfect for a peaceful retreat with everything you will need! A bright open plan kitchen/dining/living room with smart TV, large garden with patio and outdoor seating, 2 stunning bedrooms with large comfortable beds, and bathroom with power shower and bath. Host My House manages this property which is owned by Lesley & Terry Rose (who live on-site).

The Sculptors Cottage | Pass the Keys

Welcome to the Sculptor’s House which is a distinctive modern hideaway in Cuddington, a beautiful award winning village. Cuddington is a proper small village with a pub, shop, church and hairdressers as well as the Village Picture House in the village hall. It is close to several wedding venues, Nether Winchendon, Notley Abbey and Notley Barn. The nearest station is a 5 minute drive away and connects with London Marylebone (45 mins) and Bicester Village (20 mins) and Oxford (30 mins).

Peaceful village location with own entrance

The Annex is a delightful, warm, quiet and comfortable dwelling built within the garden of our village home and adjacent to our garage. Towersey is one mile from the market town of Thame, and has an excellent village pub plus access to the Phoenix Trail cycle & footpath. The Annex has its own entrance with parking space, a double bedroom with king sized bed & tv, and sitting room with fridge, microwave, coffee machine, kettle, toaster, plus tv. There is a power shower over the bath.

Self-contained barn conversion

The Farrow is a pretty self-contained annex within the grounds of Nettlebed Barn. Set in tranquil surroundings on the edge of the 12th century hamlet of Kingsey. It has the additional benefit of stunning picturesque views of rolling fields framed by the beautiful vista of the Chiltern hills. Just a 5 minute drive to Haddenham train station will give you access to central London in 40 minutes and the beautiful and historic city of Oxford in just 29 mins.

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!

A delightful barn conversion

Set in the gardens of our 17th Century house, we are offering you a well designed barn conversion which is spacious and light. We are situated in the pretty rural village of Shabbington, just outside the market town of Thame, and surrounded by the Oxfordshire/Buckinghamshire countryside. We are ideally placed for those wishing to visit local attractions such as Bicester Village, Oxford, Waddesdon Manor and Blenheim Palace.