Vacation rentals in Upper Winchendon

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Top-rated vacation rentals in Upper Winchendon

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Top guest favorite
A rustic treehouse is elevated among leafy trees, connected by a wooden staircase. Surrounding foliage creates a serene environment, while a shaded area beneath features a bench and a fire pit. The natural setting offers a sense of privacy and tranquility.
Treehouse in Hertfordshire
4.96 out of 5 average rating, 260 reviews

Tree House - Hot Tub on balcony

Our rustic Glamping Treehouse stands 5m above the ground, which is accessible via an exciting seven-meter long suspension bridge. Boasting a warm themed interior, the Treehouse offers breathtaking views over the Chess Valley, which can be seen from the balcony and through the large panoramic window. Features include a spacious king-size double bed, en-suite toilet and basin facility. The outdoor balcony is home to a shower and hot tub, the perfect spot to relax amongst the surrounding treetops!

Top 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, 176 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.

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, 827 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
Tiny home in Cuddington
4.99 out of 5 average rating, 110 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 favorite
A wood-clad cabin is nestled among trees, featuring rounded architecture and large windows. A wooden terrace with two chairs invites relaxation. A hot tub is positioned nearby, surrounded by nature and colorful autumn foliage.
Hut in Avon Dassett
4.99 out of 5 average rating, 520 reviews

Dassett Cabin - retreat, relax, romance, rewild

Disconnect from the busy … retreat beneath the canopy of an ancient woodland and soak up the views and surrounding nature. It’s not perfect. Nothing is. But luxury detailing alongside your own hot tub, hammock, sauna, indoor and outdoor showers and sun terrace is a clear nod in the right direction - all within a short walk of the friendly local pub! Short drive from the local shops and Burton Dassett Country Park Easily accessible from the M40. Close to the Cotswolds, Warwick and Stratford.

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, 226 reviews

17th Century Barn in quiet country village

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.

Superhost
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, 113 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.

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, 159 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).

Guest favorite
A modern wooden lodge is set amidst a backdrop of tall pine trees. The exterior features large glass doors opening to a spacious outdoor area with manicured grass and a concrete pathway leading to the entrance. Natural elements enhance the peaceful surroundings.
Cabin in Murcott
4.88 out of 5 average rating, 898 reviews

Woodland Lodges with Hot Tub

The perfect romantic retreat for two. Nestled in the tranquil beauty of Panshill's secluded woodland and lakes are our self-catering lodges with their very own private hot tubs. Complimentary Prosecco and Chocolates on arrival (let me know if you prefer non alcoholic) The renowned Bicester Village is just 15-minute away & as our guests will have access to an exclusive sign-up link for extra discounts. Enquire about BBQ & bike hire. Offering 20% off 2 nights & 25% off 3+ nights stays.

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, 367 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.

Top guest favorite
The historic windmill stands majestically against a backdrop of open skies, featuring a stone façade and a brick band near the top. A wooden door leads to the entrance, flanked by a gravel pathway. Lush greenery and fields are visible in the distance, enhancing the rural setting.
Windmill in Oxfordshire
4.98 out of 5 average rating, 224 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." Enjoy a luxurious stay in a historic 17th c. listed windmill and create unforgettable memories. You won’t be short of things to do—enjoy boutique shopping at the renowned Bicester Village or take leisurely walks around historic Oxford, just a 15-minute train ride away. Additionally, Blenheim Palace and Waddesdon Manor are nearby attractions worth exploring.

Top guest favorite
An aerial view captures the Pool House surrounded by lush greenery. A modern pool and hot tub are positioned alongside comfortable loungers on a spacious patio. The sliding glass doors of the house provide access to an inviting indoor area.
Guesthouse in Garsington
4.95 out of 5 average rating, 519 reviews

The Pool House

Relax and reset at the Pool House. The Pool House provides a quiet location where you can relax away from the world. Swim in our pool, heated during the warmer months. During the colder months enjoy a cold plunge, beneficial for body and mind. Ease your aches and muscles in the hot tub. Please note: you are using the pool and hot tub at your own risk, there is no life guard! Please watch children and non swimmers in the pool and hot tub at all times.

Popular amenities for Upper Winchendon vacation rentals