Vacation rentals in Upper Winchendon

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Top-rated vacation rentals in Upper Winchendon

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Guest favorite

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

4.95 out of 5 average rating, 153 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 favorite

The bright living area features vaulted ceilings with original wooden beams and skylights. A comfortable sofa sits beside a soft ottoman, while a white coffee table holds decorative items. Large glass doors lead to an outdoor space, and a wall-mounted TV is positioned for viewing.

Barn in Buckinghamshire

4.97 out of 5 average rating, 305 reviews

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.

Guest favorite

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, 737 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 favorite

The exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.

Barn in Great Milton

4.96 out of 5 average rating, 208 reviews

17th Century Barn near Le Manoir aux Quat'Saisons

A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

Guest favorite

A spacious bedroom is presented with a king-size bed adorned with hotel-quality linens. Flanking the bed are two bedside lamps providing soft illumination. A vintage dressing table and chair are positioned nearby, complemented by a stack of antique suitcases at the foot of the bed.

Cottage in Brill

4.88 out of 5 average rating, 134 reviews

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 *

Top guest favorite

The exterior of the studio is shown, featuring a charming brick facade surrounded by greenery. Double French doors open into the interior, accompanied by a small patio area with decorative chairs. The setting includes a well-maintained garden leading to a serene atmosphere.

Guesthouse in Owlswick

4.98 out of 5 average rating, 137 reviews

The Old Music Studio - retreat with tennis court

A stay in our former music studio is an immersion in nature. After a walk in the Chilterns and a fireside drink at a country pub, relax on the large comfortable sofa and watch the wildlife in the meadow from the warmth of this cosy retreat. If you’re feeling energetic, play tennis or pickleball on our court or cycle the Phoenix Trail - (Bikes/E-bikes by arrangement.) A perfect hideaway for a romantic break, recreational weekend, peaceful remote working or just recharging your batteries.

Guest favorite

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, 123 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 Please note- we currently have a skip on the main driveway- this does not impact on the annexe and there is no noise

Top guest favorite

The exterior of The Dairy is shown, featuring a charming brick facade with large windows. A wooden deck provides outdoor seating space, surrounded by lush green lawns and trees. The peaceful countryside surrounds the property, inviting relaxation in a natural setting.

Farm stay in Aylesbury

5 out of 5 average rating, 141 reviews

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).

Top guest favorite

The exterior of the modern annexe is showcased, featuring large glass doors that allow natural light to fill the interior. A spacious balcony is visible above, bordered by glass, and wooden furniture is arranged on the terrace, ideal for outdoor relaxation.

Home in Tetsworth

5 out of 5 average rating, 326 reviews

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.

Guest favorite

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

4.95 out of 5 average rating, 140 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.

Superhost

A bright living area features a cozy beige sofa and a wooden television unit. A round dining table with four chairs is illuminated by natural light from the window, decorated with floral arrangements. A potted plant adds a touch of greenery to the space.

Condo in Waddesdon

4.85 out of 5 average rating, 122 reviews

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!

Top guest favorite

The exterior of Cutter's Barn is highlighted, showcasing its stone and brick façade. Large windows invite natural light, while the surrounding countryside is visible. A gravel area leads to the entrance, with potted plants adding greenery. A bench offers a place to relax.

Cottage in Chilton

4.99 out of 5 average rating, 283 reviews

Cutter's Barn

A brick and Stone barn that sleeps 6, Cutter’s Barn has been recently refurbished to a very high standard and is set on a small livestock Farm in stunning rural Buckinghamshire. Magnificent views of rolling hills and valleys on the edge of the Chiltern Hills, but close to Oxford and excellent transport links to London. Cattle and Sheep share the surrounding pastures with abundant wild bird and animal life.