
Holiday rentals in Fair Oak
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Top-rated holiday rentals in Fair Oak
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One bedroom home.
Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.
4.94 out of 5 average rating, 426 reviews
Nettlebed Farm Holiday Lets, Barn1 of 3
* From £124 p/n +Airbnb charges Beautiful oak barn set in traditional english countryside. Placed with own access within 15 acres of private woodland and grazing land, away from the main road for peace and tranquility. Guests are able to have privacy for relaxation and enjoy views of horses grazing and the comings and goings of the British wildlife. Just 4 minute drive to the market town of Bishops Waltham or you can join and follow the infamous Pilgrims Trail and walk there in just 30 minutes.
4.97 out of 5 average rating, 417 reviews
Boutique Flat | >1 min Station | Pub | River Walks
A beautifully styled boutique flat set a stones throw away from the river in charming Shawford. Thoughtfully designed with comfort and quality in mind, it offers a calm, elegant retreat moments from riverside walks, a characterful pub opposite, and the train station just one minute away. Ideal for couples or professionals seeking a refined stay with effortless access to Winchester, South Downs, Southampton & London. Hosted by a local family dedicated to comfort, detail and a seamless stay.
5.0 out of 5 average rating, 45 reviews
The Nest
This charming 3-bed cottage with private parking and garden is situated in Shawford, near to the historic town of Winchester. Walks along the River Itchen, swimming, fishing and picnic spots are on your doorstep. Local pub in Shawford and pubs in nearby village of Twyford. Winchester is also accessible by foot ( 45 mins) or a short 5 minute train or bus away. London is an hour by train and other local attractions include Marwell Zoo, Peppa Pig World, South Coast, Portsmouth and New Forest.
4.81 out of 5 average rating, 162 reviews
The Limes, Colden Common, Winchester, with parking
Escape to peace and comfort at The Limes, a spacious and private ground-floor annexe set in a rural village just south of Winchester. Tucked well back from the main road and overlooking a beautiful garden with countryside views, this light-filled retreat offers a true home-from-home experience. With its own private entrance, off-road parking, and easy access to Winchester (just 15 minutes away), it’s an ideal base for relaxing breaks, work trips, or exploring the surrounding area.
4.99 out of 5 average rating, 156 reviews
Newly refurbished Bungalow
Enjoy a relaxing stay in our newly refurbished 3-bed bungalow in peaceful Fair Oak. Ideal for families and groups, & business/work colleagues! Featuring 3 double bedrooms (one en-suite), plenty of storage, a modern bathroom, and a fully equipped kitchen with breakfast bar and large dining table for 8 people. Walk to village shops and pubs, with easy access to Winchester, Southampton, the Ageas Bowl (10 mins), and Paulton's Park / Peppa Pig World (20 mins) Eastleigh (5 mins)
4.94 out of 5 average rating, 62 reviews
Room with a view
You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.
4.92 out of 5 average rating, 426 reviews
Durley, Hampshire UK - secluded private 1 bed flat
The flat is a self-contained one bedroom first floor apartment located in the quiet and picturesque village of Durley. It is above the garage block beside the owners' property situated on the first floor, accessed via its own front door. Durley is only 10 minutes from junction 7 of the M27, or 15 minutes from the M3 and a great central location situated roughly halfway between the cities of Southampton and Winchester yet only 30 minutes from the New Forest.
4.96 out of 5 average rating, 90 reviews
Pretty self contained annexe
Pretty, self contained annexe with its own entrance, located between the historic city of Winchester & Southampton and on the doorstep of the New Forest National Park. Great travel links - M3/M27, Southampton Airport & Southampton Parkway station. Studio comprises double bed, kitchen with oven, hob, fridge & microwave. Breakfast bar, which doubles as a workspace, shower room and shared use of patio and garden. We also have a young, bouncy dog!
4.97 out of 5 average rating, 219 reviews
Cosy Riverside Escape Near Winchester
* Cosy autumn evenings beside the riverside fire pit * Morning coffee overlooking the water * Wildlife spotting from the garden * Peaceful, uninterrupted river views Wake to birdsong and sweeping views of the River Itchen, where kingfishers, herons and other wildlife are regular visitors. Nestled at the water’s edge, Dove Cottage is a peaceful riverside retreat made for slow mornings, cosy evenings and reconnecting with nature.
5.0 out of 5 average rating, 61 reviews
The Cottage in Compton
Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!
4.99 out of 5 average rating, 224 reviews
New barn conversion
Brand new! Found at the end of a quiet lane, surrounded by fields, this stunning barn set is in beautiful countryside within the South Downs National Park. An ideal retreat for families and friends alike, lovely walks, cycle routes, local attractions all within easy reach. The barn is recently built with all the amenities needed for a home-from-home feel.
5.0 out of 5 average rating, 36 reviewsPopular amenities for Fair Oak holiday rentals
Other great holiday rentals in Fair Oak

Stunning peaceful base to explore Hampshire
5.0 out of 5 average rating, 85 reviews
Luxurious 5 Bedroom 3.5 Bathroom House
5.0 out of 5 average rating, 20 reviews
Beautiful Cottage by RiverItchen
4.97 out of 5 average rating, 31 reviews
Great place to work or relax
4.92 out of 5 average rating, 50 reviews
Self Contained Annexe Hampshire
4.94 out of 5 average rating, 36 reviews
Scandinavian Bbq Hut ‘Alaska’
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The Stable House
4.97 out of 5 average rating, 90 reviews
The Den
5.0 out of 5 average rating, 45 reviewsDestinations to explore
- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- Longleat Safari Park
- Goodwood Motor Circuit
- Thorpe Park Resort
- Stonehenge
- South Downs National Park
- Southbourne Beach
- Windsor Castle
- LEGOLAND® Windsor Resort
- Boscombe Beach
- Bracklesham Bay
- Highclere Castle
- Chessington World of Adventures Resort
- Mudeford Quay
- Durdle Door Holiday Park
- Winchester Cathedral
- The Tank Museum
- Ascot Racecourse
- University of Reading
- Kimmeridge Bay
- Bournemouth International Centre





