
Holiday rentals in Upper Winchendon
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Top-rated holiday rentals in Upper Winchendon
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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.
4.95 out of 5 average rating, 198 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.
5.0 out of 5 average rating, 67 reviews
"The Annexe" modern self-contained detached studio
Modern detached studio set on an equestrian family home, on the outskirts (2miles away) of the beautiful village of Quainton. Quainton offers wonderful walks and views, a working Windmill, a delicious cafe, a shop and a friendly pub - perfect for that much needed getaway. Whether you are staying for business or time off, there are plenty of lovely restaurants and pubs to visit locally. Convenient location for Bucks Railway centre, Waddesdon, Bicester and within 30min of Silverstone and MK Bowl.
5.0 out of 5 average rating, 38 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.
4.99 out of 5 average rating, 134 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.
4.89 out of 5 average rating, 132 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.
4.97 out of 5 average rating, 491 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.
4.93 out of 5 average rating, 120 reviews
The Windmill Blackthorn Hill, Nr. Bicester Village
Featured in the 'Times Newspaper' Top 10 best Places to Stay with Spectacular Views: "A truly amazing experience." Perfect for a romantic escape for 2 or a memorable getaway with family or friends, sleeping up to 4 adults max (+13), with reduced rates for couples wishing to use a single bedroom. If you’d prefer to use both bedrooms, the second bedroom can be prepared for a small additional one-off fee. Bookings for three or four guests automatically include both bedrooms.
4.97 out of 5 average rating, 234 reviews
Business Weekday Stay & Couples Weekend Retreat
The Lodge is a beautifully designed escape created with couples & 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. Saunter to the local pub 3 mins walk. Min 2 night stay.
4.84 out of 5 average rating, 31 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.
4.94 out of 5 average rating, 192 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.
4.94 out of 5 average rating, 96 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!
4.84 out of 5 average rating, 162 reviewsPopular amenities for Upper Winchendon holiday rentals
Other great holiday rentals in Upper Winchendon

The Bee Hive
4.89 out of 5 average rating, 80 reviews
Cheerful 3 bedroom property set in the countryside
4.96 out of 5 average rating, 98 reviews
The Aylesbury Family Retreat Home with Parking
5.0 out of 5 average rating, 10 reviews
Completely refurbished cottage in heart of village
4.97 out of 5 average rating, 34 reviews
6BR|Sleeps 13|Contractor|Garden|WiFi|Parking
4.95 out of 5 average rating, 19 reviews
Haydon Hill House
4.99 out of 5 average rating, 70 reviews
Peaceful self-contained cabin in Buckinghamshire
4.98 out of 5 average rating, 44 reviews
The Long Barn - With Pool and Games Room
5.0 out of 5 average rating, 5 reviewsDestinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- ExCeL London
- The O2
- Tower Bridge
- Silverstone Circuit
- Clapham Common
- Emirates Stadium
- Cotswolds AONB
- Victoria Park
- University of Oxford
- Tottenham Hotspur Stadium
- Thorpe Park Resort
- The National Bowl
- Blenheim Palace
- Big Ben
- Buckingham Palace
- Alexandra Palace
- London Eye





