Vacation rentals in Upper Winchendon

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Top-rated vacation rentals in Upper Winchendon

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Guest favorite

Cottage in Cuddington

4.96 out of 5 average rating, 109 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.

Dec 16 – 23

G$49,524 GYD per night

Guest favorite

Farm stay in Aylesbury

5.0 out of 5 average rating, 104 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 and more; bright open plan kitchen/dining/living room with smart TV, large garden with patio and outdoor seating, master bedroom with super king bed and TV, second bedroom with king bed, bathroom with power shower and bath. Host My House manages this property which is owned by Lesley & Terry Rose

Aug 24 – 31

G$55,071 GYD per night

Guest favorite

Barn in Great Milton

4.95 out of 5 average rating, 139 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.

Jul 26 – Aug 2

G$76,345 GYD per night

Guest favorite

Chalet in Cuddington

4.87 out of 5 average rating, 157 reviews

Village Location, Nr Thame

Located at the bottom of the village, accessed via a sleepy single track road, Little Wyncot is set within the secure grounds of our family’s 17th Century thatched cottage. Enjoy lovely circular walks right on your doorstep, taking in Nether Winchendon - the home of the popular Manor House wedding venue. Relax and enjoy a drink and/or a bite to eat in the village pub, The Crown. In the surrounding area, you’ll have access to National Trust's magical Waddesdon Manor and market town Thame.

Aug 8 – 15

G$21,492 GYD per night

Guest favorite

Tiny home in Aylesbury

4.97 out of 5 average rating, 155 reviews

The Woodland Retreat With 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.

Jan 10 – 17

G$80,033 GYD per night

Guest favorite

Guest suite in Towersey

4.96 out of 5 average rating, 355 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

Aug 25 – Sep 1

G$21,342 GYD per night

Guest favorite

Condo in Granborough

4.82 out of 5 average rating, 453 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.

Nov 17 – 24

G$20,208 GYD per night

Guest favorite

Guesthouse in Drayton Parslow

4.95 out of 5 average rating, 128 reviews

The Former Stables

A self-contained, one bedroom apartment which was converted from stables around 10 years ago. It is around 550 sqft and has a large double bedroom with vaulted ceiling, a comfortable open plan living room with fully equipped kitchen and a limestone shower room. And of course, it has a stable door! Located in the middle of a small village which is approximately 15 mins drive from Milton Keynes and Leighton Buzzard where fast trains to London take just 30 minutes.

Jun 22 – 29

G$20,156 GYD per night

Guest favorite

Guesthouse in Worminghall

4.91 out of 5 average rating, 106 reviews

Charming barn conversion with vast living space

Set alongside our beloved family home, in 7 acres of open farmland, this wonderful space offers a welcome retreat from the stresses of everyday life. Worminghall is predominantly a farming village, within easy vehicular access to Oxford and the market town of Thame. Situated on the Oxfordshire/Buckinghamshire borders, it's the perfect location if you are visiting for a wedding or function nearby, or simply wish to explore the area's many local attractions.

Sep 27 – Oct 4

G$32,758 GYD per night

Guest favorite

Barn in Kingsey

4.93 out of 5 average rating, 409 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.

Oct 23 – 30

G$21,574 GYD per night

Guest favorite

Barn in Shabbington

4.97 out of 5 average rating, 296 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.

Sep 27 – Oct 4

G$29,017 GYD per night

Guest favorite

Cottage in Chilton

4.99 out of 5 average rating, 248 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.

Jan 15 – 22

G$49,425 GYD per night