Vacation rentals in Upper Winchendon

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Top-rated vacation rentals in Upper Winchendon

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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

4.96 out of 5 average rating, 159 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, 310 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, 752 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

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, 89 reviews

Modern Self-Contained Detached Studio in Village

The Studio is a newly-built, 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, Birmingham & London), 15 minutes from M40 motorway and 4 miles north of Thame.

Top guest favorite

A charming exterior view of a black cabin surrounded by lush greenery. A blossoming tree provides shade to a small white table and chairs set on a paved area. The sky displays soft clouds and bright blue hues, enhancing the peaceful setting.

Cabin in Waterstock

4.98 out of 5 average rating, 126 reviews

Boutique couples hideaway – "The Den"

Privacy, peace and tranquility along with a generous artisan breakfast hamper awaits couples at “The Den”. Single guests also welcome and well-behaved furry friends too! Completely self-contained. Just 6 miles from central Oxford. Recently refurbished to the highest of standards. Enjoy peace and quiet with all these features: Super-comfy double bed, lounge area with Smart TV inc Netflix, WiFi, kitchenette with Belfast sink, mini fridge, microwave, toaster & kettle plus a beautiful en-suite.

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, 144 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 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

4.95 out of 5 average rating, 74 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.

Top guest favorite

A living room features a stone fireplace with a modern design, complemented by a striped armchair and a soft sofa. Natural light pours in through large glass doors that lead to a private garden, with light-colored curtains framing the windows. A textured rug covers the floor.

Home in Dinton

4.96 out of 5 average rating, 50 reviews

Lavender Keep

Lovely two bedroom annex with a private entrance and a gated garden. The living room overlooks the garden and there’s a real log burner for added warmth. Enjoy off road parking for convenience. A charming village pub is just a minutes walk away. Ideally located just 4 miles away from Thame and Aylesbury and with easy access to Oxford and London via nearby stations. There are also many fantastic places to visit close by such as Waddesdon Manor, Wycombe caves and Bicester Village.

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

4.94 out of 5 average rating, 145 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.

Top guest favorite

A compact interior of the Shepard's hut is showcased, featuring a cozy sleeping area with a spacious bed and natural light filtering through a window. A small dining table is set nearby, complemented by wooden cabinetry and a simple sink area, providing essential amenities.

Shepherd’s hut in North Marston

4.96 out of 5 average rating, 254 reviews

WWII Bomb Trailer Shepherd’s Hut

Get away from the hustle and bustle of busy life and enjoy our secluded Shepards hut retreat. Set on the outskirts of the Chilterns, a stones through from the quaint village of North Marston. You will find yourself on a working farm with little but the flora and fauna to keep you company. The hut is situated east facing, the sun creeks over the hill to uncover a stunning view. Discover the gorgeous landscape that surrounds this place and enjoy the simple life.

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

4.86 out of 5 average rating, 127 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

A modern living area features a comfortable brown leather sofa and a reclining chair, complemented by a light rug on wooden flooring. A glass door provides access to a balcony, while a TV and a small dining table enhance the space. Natural light fills the room.

Apartment in Haddenham

5 out of 5 average rating, 59 reviews

Modern Apartment in Haddenham!

Modern two-bed apartment with outstanding views and stylish open plan layout. It is very conveniently situated just a 4min walk to the station for London Marylebone (under 40min), Bicester Village, Oxford and Birmingham and a walking distance to local café’s and pubs. There is a Co-op right below, which is very handy, and free parking spaces.