Holiday houses in Upper Winchendon

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Upper Winchendon

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
A private courtyard features a small round table and two chairs, surrounded by gravel. Potted plants add greenery, and a wooden fence provides an unobstructed view of the expansive fields beyond. A decorative lattice offers partial privacy while enhancing the outdoor ambiance.
Casa particular in Wendover
4.9 out of 5 average rating, 314 reviews

The Nook at Pine View - set in Roald Dahl Country

The Nook at Pine View, is set within the Chiltern Hills in a designated Area of Outstanding Natural Beauty. In the heart of "Roald Dahl Country", Cobblers Hill is famously written within the pages of "Danny Champion of the World". The Nook benefits from stunning rural views and the peace & quiet of country living but with easy access to award-winning restaurants, pubs & cafes all just a short drive. A 45 min train to London. The surrounding area has some renowned country walks and cycle paths.

Top Guest favourite
A well-maintained garden features a stone pathway leading to the cottage, bordered by green lawns and vibrant red flowers. Various outdoor seating options are scattered throughout the area, with potted plants adding a charming touch. A distant shed is visible, complementing the serene landscape.
Cottage in Cuddington
4.96 out of 5 average rating, 171 reviews

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.

Top Guest favourite
This bright kitchen features sloped ceilings with three skylights allowing natural light to flood the space. A modern kitchen area is equipped with a refrigerator, microwave, and stove. A simple wooden table with two red chairs is positioned in the center, enhancing the inviting layout.
Apartment in Woolstone
4.97 out of 5 average rating, 799 reviews

A tranquil oasis in the heart of Milton Keynes

Guests have exclusive access to this spacious, self contained one bedroomed apartment which has: private entrance, free wifi and off road parking. Just a few minutes drive from the theatre and shopping centre, Woolstone retains much of its quiet village character and ambience including canalside and river walks, 13th century church and 2 fabulous Pub/Restaurants. It is convenient for the Bowl Arena, Bletchley Park, Woburn Safari, the M1 motorway(10 mins), Luton Airport (20 mins) and London.

Guest favourite
A wooden cabin with an arched design is framed by tall trees, creating a natural setting. Steps lead to a spacious deck area, which includes potted plants and a dark wood BBQ grill under a covered space.
Tiny home in Buckinghamshire
4.97 out of 5 average rating, 808 reviews

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.

Top Guest favourite
A modern kitchen is displayed, featuring light grey cabinetry and wooden countertops. An induction oven and cooking utensils are visible. A dining table with two benches is positioned near the window, and a washing machine stands adjacent to the cabinetry. Solid oak flooring enhances the space.
Tiny home in Cuddington
4.99 out of 5 average rating, 105 reviews

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.

Top Guest favourite
The exterior of the barn conversion is depicted, showcasing a traditional black wooden façade. A patio area with a round table and two wooden chairs is visible, accompanied by a large umbrella. Lush greenery and mature trees surround the property, providing a tranquil setting.
Cottage in Granborough
5 out of 5 average rating, 109 reviews

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.

Top Guest favourite
The exterior view of The Annex is featured, showcasing a charming black wooden building with a steeply pitched roof. A set of stairs leads to the upper level, and large windows allow for natural light. Gravel lines the entrance, framed by landscaping.
Guest suite in Towersey
4.96 out of 5 average rating, 515 reviews

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.

Guest favourite
A path leads to the entrance of the studio apartment, bordered by raised flower and herb beds. The covered patio area features wooden beams and is situated in front of the large glass doors, allowing natural light to illuminate the entrance.
Condo in Granborough
4.83 out of 5 average rating, 551 reviews

The Herb Garden

A light, airy, ground-floor, single-storey studio apartment. There is a large kitchen and comfortable seating area, and a private patio / garden area. We are well situated for visiting Silverstone, Addington, Oxford, Bicester Village, Waddesdon Manor, Stowe Gardens and Bletchley Park. Also good for working in Milton Keynes or Aylesbury and for trains into London and Birmingham. The apartment has disabled access and ample off-road parking. We are happy to accommodate well-behaved dogs.

Guest favourite
A bright studio room is presented with a spacious bed and light wood flooring. A small kitchenette area is visible, featuring a microwave and a coffee machine. A private door leads to an outdoor seating area, while natural light filters through a nearby window.
Home in Haddenham
4.94 out of 5 average rating, 165 reviews

The Annexe

Located in the historic centre of Haddenham, the annexe is a bright, contemporary self contained studio room with private access and parking. Moments away from pubs, the award winning Norsk cafe, shops and amenities, it has everything you need on our doorstep. Haddenham & Thame train station is a 15 min walk away making it a perfect location for visiting Oxford, London or shopping at Bicester village, whilst the picturesque market town, Thame, is just 3 miles away.

Guest favourite
The exterior of Nettlebed Barn is depicted, featuring a charming brick facade with decorative black trellises on the windows. A gravel pathway leads to the entrance, surrounded by neatly trimmed hedges. A sign indicating 'Nettlebed Barn' is prominently displayed near the building.
Barn in Kingsey
4.93 out of 5 average rating, 502 reviews

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.

Top Guest favourite
The open plan living area features a spacious gray sofa adorned with colorful cushions, positioned around a glass coffee table. Large glass doors allow natural light to flood the space, with views of the garden. A plush ottoman and a media unit complement the inviting atmosphere.
Barn in Shabbington
4.96 out of 5 average rating, 495 reviews

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.

Guest favourite
A slate sign displaying the word 'THE ANNEXE' is illuminated by delicate string lights. The sign is mounted on a wooden backdrop, creating a warm and welcoming entry point.
Apartment in Oakley
4.9 out of 5 average rating, 139 reviews

1 bedroom annexe with parking. Single occupancy

Cosy 1 bed self contained annexe. Single occupancy Recently renovated- Small double bed, kitchen, shower, WC. Private entrance with key lock. The annexe is to the left of the main property Off road parking. Midpoint to Oxford and Buckinghamshire- postcode- HP18. Lovely countryside walks and local pubs. Suitable for commuters. Car essential 14square metres Check in from 4pm

Popular amenities for Upper Winchendon holiday rentals