Holiday rentals in Middle Assendon

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Top-rated holiday rentals in Middle Assendon

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Top guest favourite
A welcoming entrance is framed by a rustic wooden gate and lush greenery. The shepherd's hut is visible in the background, with a soft sunset illuminating the sky and reflecting off the structure. Pathways bordered by wildflowers lead towards the fields beyond.
Shepherd’s hut
4.99 out of 5 average rating, 616 reviews

Luxury Shepherd's Hut with stunning sunset views!

Welcome to Honeysuckle, our luxury shepherd's hut with stunning views across the fields in the Chilterns. In the evenings sit and watch the sun go down around your fire pit or stay cosy indoors with your log burner. We are a working farm and you may see the tractor trundle past feeding our herds of Texal sheep (Lambing right in front of you in March/April 2025!) and Limousin cows grazing in fields, or watch the many birds. You have your own secluded, fenced and private garden area with seating.

Superhost
A garden terrace is shown with a table and four chairs, offering a view of a lush green pasture where horses graze. A wooden fence delineates the space, enhancing the rural ambiance.
Barn
4.83 out of 5 average rating, 144 reviews

Idyllic, Rural Barn in Henley on Thames.

The Barn is equipped with everything you need to have a relaxing stay in the countryside. It overlooks 10 acres of pasture, with its own private garden terrace and entrance. The picturesque river and town centre of Henley on Thames is a level one mile walk (approximately), and offers a variety of shops, pubs and restaurants. This is a great location for a relaxing break and the perfect spot to use as a base to explore the beautiful Chiltern Hills National Landscape! *Now with upgraded WiFi*

Top guest favourite
An outdoor terrace is furnished with a long bench and a vibrant table covered in a decorative tablecloth, ideal for dining. A collection of flowers and a bottle of wine are displayed on the table, complemented by the surrounding greenery and brick pathway.
Guest suite
4.91 out of 5 average rating, 34 reviews

Countryside retreat set within beautiful woodlands

Our self contained annex sits in a Peaceful & Rural location with stunning countryside views of the bluebell woodlands beyond. Located only 3 miles from the historic town of Henley on Thames and within view of the beautiful National Trust’s Grey’s Court, we are ideally located to explore the local area whilst remaining secluded away from the hustle and bustle . Walkers & bikers are spoilt for choice with footpaths leading from the garden including one that leads to a wonderful local pub.

Guest favourite
A modern kitchen area is featured with sleek black cabinets and a stylish countertop. Natural light is brought in through a skylight and large windows. A wooden dining table accompanied by chairs is seen, creating a welcoming space for meals.
Tiny home
4.91 out of 5 average rating, 367 reviews

The Cabin, a Gorgeous Hideaway in Henley on Thames

The Cabin, Henley on Thames is a gorgeous space for you to enjoy your holiday. Surrounded by nature, guests have the pleasure of pheasants, deers, foxes and Red Kites. Located in the back garden of our house you can walk straight into fields and the beautiful Chiltern hills. Its only a 5 minute drive/ 15 minute walk from the centre of the historic town of Henley on Thames. Newly built it features underfloor heating, and brand new designer fittings. Access via woodland path or garden stairs.

Top guest favourite
A cozy sleeping area features a spacious bed with neutral bedding against a softly colored wall. A small armchair and a light-colored rug complement the wooden flooring. Wall-mounted shelves display framed images, and a small closet provides additional storage.
Guest suite
4.94 out of 5 average rating, 455 reviews

Completely separate self-contained studio flat

Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

Top guest favourite
An open plan living area is highlighted by vaulted ceilings and natural wood beams. A kitchenette with modern appliances is complemented by a breakfast bar featuring two stools. Natural light streams in through large glass doors, leading to a cozy seating area and inviting decor.
Guest suite
4.98 out of 5 average rating, 105 reviews

Delightful, open plan studio in Brightwell Baldwin

Delightful 1 bedroom detached studio with private entrance and onsite parking. Character, spacious open plan living, beautifully furnished, vaulted ceilings and large walk-in shower room. Outside seating area with lovely views over main garden. Ideal for a relaxing break with local walks and renowned country pub less than a 10 min walk. Brightwell Baldwin is a small hamlet close to the market and historic town of Watlington. Henley-on-Thames and Oxford City Centre are a short drive away.

Superhost
A well-lit bedroom features a spacious bed with decorative pillows and a soft gray blanket. Two bedside tables with lamps flank the bed, while a full-length mirror and artwork enhance the decor. Natural light enters through the double doors leading to a small outdoor area.
Flat
4.86 out of 5 average rating, 127 reviews

Elegant Central Henley Apartment

Enjoy the charm of Henley-on-Thames from this elegant, modern apartment on Tuns Lane — right in the heart of town. Parking is easy, with free on-street options and a nearby public car park, both within 5 minutes’ walk. You’ll be just steps from Market Square’s independent shops, pubs, cafés, and restaurants, and a short stroll to the Royal Regatta and Festival sites. The town hall, theatre, and cinema are moments away, and Henley train station is only a 7-minute walk.

Top guest favourite
A bedroom features a standard double bed with a blue and white striped duvet. Nightstands with matching lamps are on either side. Wooden paddles adorn the wall above the bed, while a door leads outside. Natural light enters through a nearby window.
Flat
4.97 out of 5 average rating, 237 reviews

Cosy annexe by shops/parking 19 min walk to Henley

The Hoppy Annexe is a self-contained space, set in a little garden on a peaceful road with free parking, a 15-20 minute walk down the hill to Henley town centre. It is suitable for either a single person or a couple - there's a standard sized double bed, ensuite bathroom with shower and a small kitchenette. Beautiful countryside walking routes are just a minutes away and Henley town centre, with its shops, cafes, restaurants and river front is within easy reach.

Top guest favourite
A charming wooden barn is set amidst lush greenery and tall trees. A tranquil pond with water lilies reflects the surrounding foliage. Bright sunlight illuminates the scene, enhancing the peaceful outdoor space and the rustic charm of the barn.
Guest house
4.98 out of 5 average rating, 262 reviews

The Barn at The Grove

The Barn is a self-contained recently converted space in the heart of the Chilterns. It is close to the riverside towns of Henley-on-Thames and Marlow and the surrounding Chiltern countryside. It is located on the edge of the village of Frieth with nearby farm shops and local gastro-pubs within a 5 min drive. The Barn is in a private and peaceful location with off-street parking. It is perfect for couples, solo travellers and small families.

Guest favourite
An inviting living area features a blend of a brown leather sofa and a large blue sofa, both oriented toward a TV. A stylish coffee table sits atop a patterned rug, while a decorative fireplace and greenery add character to the space.
Apartment
4.91 out of 5 average rating, 134 reviews

Central Hidden Gem

If it is a base in the centre of Henley's beautiful market town you are seeking, then Central Hidden Gem is the perfect spot. The apartment proudly exhibits a combination of a modern style with contemporary quirks, creating a stylish yet homely air. Sleeping a maximum of five guests across two bedrooms and one sofa bed, Central Hidden Gem is ideal for small families or groups of friends who want to explore all that the town has to offer.

Guest favourite
A shepherd's hut is nestled among trees, featuring a green exterior and wooden accents. The front door is flanked by small windows, and a rustic wooden table with seating is positioned outside, complemented by a flower pot. A cozy atmosphere is created by the surrounding woodland.
Shepherd’s hut
4.95 out of 5 average rating, 58 reviews

Bluebell -Shepherds Hut, Henley on Thames

Our Beautiful Shepherds Hut named Bluebell is one of 4 cabins nestled in stunning woodlands, on a private estate just outside Henley-On-Thames. Come and relax, unwind and take time out of the hustle and bustle at Red Kite Retreats. Why not stay during the Autumn and Winter months? Cosy up in front of the log burners ( All accommodation comes with heating i.e. radiators or underfloor heating so you can be cosy all day and night)

Top guest favourite
A spacious bed is positioned against a neutral-colored wall, complemented by decorative cushions. A tall plant adds a touch of greenery to the scene, while soft lighting from a wall fixture creates a calm ambiance.
Guest suite
4.96 out of 5 average rating, 253 reviews

"Kotimme" Annexe in beautiful area near Thames

Lovely Annexe / Suite with a separate lounge, Bedroom ( Kingsize Bed ) & Bathroom - ideal for a couple. Sole Use. Attached to the main house but own private entrance & self check-in. Parking on a drive. Smart TV. We don't have a Kitchen but there is a Fridge, Kettle, Toaster and Tea & Coffee, and Milk & Juice are provided. We offer boat trips for an extra fee. Train links to Henley, Reading & London. 5 mins to River Thames

Popular amenities for Middle Assendon holiday rentals

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