Vacation rentals in Middle Assendon

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Top-rated vacation rentals in Middle Assendon

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Top guest favorite

A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.

Cottage in Warfield

4.98 out of 5 average rating, 282 reviews

Newly refurbished luxury 2 bedroom cottage

Luxury cottage at Hayley Green that accommodates up to 4 people. Newly refurbished in semi-rural setting. Full of character with all the amenities you need for a luxurious comfortable stay. The perfect relaxing getaway for couples, family and friends. The cottage is located 16 minutes to Windsor, 30 minutes to Henley on Thames, 11 minutes to Ascot, 9 minutes to Legoland, 6 minutes drive to Lapland Ascot.We are also close to Bracknell train station where you take a train to London under 1 hour.

Guest favorite

An open-plan sitting room features a grey sectional sofa with bright green accent pillows, creating a comfortable seating area. A dark wooden coffee table is centrally placed on a textured rug, with a modern clock visible on the wall. The kitchen area is partially seen in the background.

Guesthouse in Henley-on-Thames

4.87 out of 5 average rating, 196 reviews

Charlotte's Place

This beautiful annexe is a new addition to our home and has provided us with an amazing space within our garden. The annexe has a open plan sitting room with kitchen and breakfast bar at one end. The bedroom has a super king size bed that can be set up as a twin room if required and there is a separate bathroom with double walk in shower. This is an ideal space for business trips with its own access, wifi, usb points and the ability to self cater if you wish but equally a great weekend getaway.

Top guest favorite

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 in Ewelme

4.99 out of 5 average rating, 546 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.

Guest favorite

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 in Oxfordshire

4.91 out of 5 average rating, 328 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.

Guest favorite

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 in Oxfordshire

4.86 out of 5 average rating, 132 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 Area of Outstanding Natural Beauty.

Guest favorite

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.

Apartment in Oxfordshire

4.89 out of 5 average rating, 112 reviews

Elegant Central Henley Apartment

Enjoy the beautiful market town of Henley-on-Thames from this elegant modern apartment, located on Tuns Lane, right in the town centre. Nearby paid (public car park) and free (road) parking available, within 5 minutes walk. A few minutes walk from the Royal Regatta and Festival sites and only 100m walk to Market Square in the centre of town with many independent shops, pubs, cafes and restaurants. Close to the town hall, theatre and cinema. 7 minutes walk to Henley train station.

Top guest favorite

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.

Apartment in Oxfordshire

4.97 out of 5 average rating, 218 reviews

Cosy annexe by shops/parking, 19min 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.

Guest favorite

A serene landscape unfolds with gentle hills and lush greenery, set against a vibrant sunset sky. The foreground features a rustic brick wall, partially covered by grass and wildflowers, providing a natural boundary to the expansive fields beyond.

Home in Skirmett

4.9 out of 5 average rating, 115 reviews

Gorgeous Cottage in Skirmett with Parking

This gorgeous 3 bedroom cottage, is in the quiet village of Skirmett, situated in the Hambleden Valley, in a particularly pretty area of the Chilterns. Many films and TV series have been filmed in the area, as it is often thought of as quintessentially English. Just a hop and a skip from London and its airports and a short distance from Marlow, Henley or High Wycombe stations... come and step back in time and enjoy a rural setting you won't forget.

Top guest favorite

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A white shelving unit displays various items, including vases and artwork. Natural light enters through windows, creating a cozy ambiance. Decorative mirrors add to the room's openness.

Home in Nettlebed

4.97 out of 5 average rating, 33 reviews

Outstanding quality secluded country cottage

Quiet getaway just an hour from Central London located in the heart of the Chilterns with immediate access to large nature reserve yet only a 5 min drive to Henley on Thames. Stylish and spacious contemporary bungalow, secluded garden, ideal for walking or biking enthusiasts, horse back riding easily available. Wide selection of top quality restaurants on your doorstep as well as being just 40 mins from Oxford and Reading. Not suitable for children

Top guest favorite

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.

Guesthouse in Buckinghamshire

4.98 out of 5 average rating, 253 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 favorite

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.

Condo in Henley-on-Thames

4.91 out of 5 average rating, 123 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.

Top guest favorite

The exterior of the cottage is showcased, featuring a charming wooden façade with a light green front door. Lush greenery surrounds the property, including neatly trimmed hedges and small decorative plants in pots. A gravel pathway leads to the entrance, under a partly cloudy sky.

Home in Oxfordshire

4.99 out of 5 average rating, 75 reviews

The Little Cottage At The Barn

This cottage is for those who want a peaceful location but also want to be able to walk into the beautiful town of Henley on Thames, or perhaps take one of the footpaths up into the Chiltern hills. It is a part of a charming barn conversion, with its own garden and parking at the end of a secluded private road. Recently refurbished it offers a relaxing environment with comfortable 'cottage chic' decor.