Holiday houses in Upper Winchendon

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Top-rated holiday rentals in Upper Winchendon

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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

4.95 out of 5 average rating, 194 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.

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Top Guest favourite

A charming wooden barn exterior is framed by lush greenery and brightly painted shutters. A gravel pathway leads to the entrance, bordered by flowering plants, enhancing the tranquil setting. Clear blue skies overhead complement the warm wooden tones of the structure.

Guesthouse in Quainton

4.97 out of 5 average rating, 112 reviews

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.

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Top Guest favourite

A spacious outdoor dining area is equipped with a dark rectangular table and ten woven chairs, positioned adjacent to a large, inviting swimming pool. The pool's clear blue water reflects the sky, while colorful sun loungers are arranged nearby against a backdrop of sweeping countryside views.

Home in Nether Winchendon

5.0 out of 5 average rating, 65 reviews

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.

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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, 131 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.

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Guest favourite

The master bedroom features exposed oak beams and hardwood flooring. A spacious bed is adorned with floral patterned pillows and a textured throw. Soft lighting from two bedside lamps enhances the peaceful ambiance, while a wooden door adds character to the unique design.

Barn in Brill

4.88 out of 5 average rating, 129 reviews

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.

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Top Guest favourite

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

5.0 out of 5 average rating, 168 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).

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Top Guest favourite

A modern wooden cabin blends into its woodland surroundings, featuring large glass windows that offer views of the forest. An outdoor kitchen is visible beside a spacious dining table crafted from natural wood. Comfortable seating arrangements create a welcoming outdoor space.

Tiny home in Aylesbury

4.97 out of 5 average rating, 484 reviews

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.

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Top Guest favourite

A bright window seat with two cushioned pillows offers an inviting view of the lush garden. Wooden frames and charming details enhance the tranquil atmosphere. Light streams in, highlighting the greenery outside and the colorful flowers in bloom.

Guest suite in Haddenham

4.94 out of 5 average rating, 118 reviews

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.

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Superhost

Home in Dinton

4.81 out of 5 average rating, 26 reviews

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.

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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, 189 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.

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Guest favourite

The exterior of the Coach House is illuminated softly at night, highlighting the brick facade and a welcoming door. A small seating area with two chairs is visible, surrounded by flowering plants and lush greenery, creating a peaceful ambiance under the moonlight.

Cottage in Waddesdon

4.94 out of 5 average rating, 95 reviews

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.

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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

4.84 out of 5 average rating, 159 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!

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