Holiday 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 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.

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.

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 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.

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.

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).

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.

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.

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!