Holiday houses in Chale Green

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Top-rated holiday rentals in Chale Green

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Top Guest favourite

Apartment in Ventnor

The Ocean Suite, Ventnor Beach (with Sauna)

Laid back beachfront living at its best, a romantic escape - popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner 2025 LUXLife Awards, Best Coastal Retreat, South England. 52 sq metres and open plan, with bi-fold windows/doors creating a beautiful space of just you and the ocean. With 2 private balconies, one south facing for sunbathing, the second with a private sauna, combine with a swim in the sea just a few steps away. No pets but baby welcome!

FamilyValueBreakfast

4.99 out of 5 average rating, 180 reviews

Top Guest favourite

A single-storey cottage is showcased, featuring a natural stone exterior with a red brick trim. The vibrant greenery of the lawn surrounds the building, and a blooming rosebush is positioned near a large window. Sunlight casts a soft shadow across the ground.

Cottage in Kingston

Pretty cottage in lovely area near south coast

WARM, COMFORTABLE, AMAZING LOCATION A super-cosy, rural getaway with an unbelievable view, set in the grounds of a medieval manor but feels private. Perfect for a family, a couple, friends. Looks out onto a lake and the downs. 10 mins to the coast, within 30 mins to anywhere on the island - village pubs, seaside towns, foodie restaurants, beaches, adventure parks, castles, cliff-top walks. An incredibly peaceful and restorative haven for 2 to 4 people. A very tranquil yet very handy location.

LocationFamilyParking

4.94 out of 5 average rating, 70 reviews

Top Guest favourite

A scenic view features golden hay bales scattered across a field, with a cluster of houses in the foreground. The coastline in the distance showcases cliffs and the sea, framed by a clear blue sky.

Condo in Isle of Wight

Chale Bay Farm - Needles' View

Needles' View at Chale Bay Farm is an air-conditioned family-friendly self-catering apartment with stunning views towards the Needles. The living area features a contemporary open-plan, fully-equipped kitchen with oven, hob, microwave, fridge, freezer, dishwasher and combined washer/dryer and adjacent dining and lounge/sun-room. Sleeps up to 4 (or 5 with sofa-bed or cot) but you can add more space by booking our stand-alone room Tennyson View or one or more of our other adjacent apartments.

ValueFamilyQuiet

4.98 out of 5 average rating, 120 reviews

Top Guest favourite

Holiday home in Isle of Wight

Gotten Manor Estate - The Left Cart House

A remote, 200-year-old stone barn converted into two self catering cottages, retaining the open facade of the original building, situated on the Gotten Estate . Hidden at the end of a country lane, tucked away at the foot of St. Catherine’s Down, a mile inland from the south coast of the Isle of Wight, in the middle of an AONB. Ideal for walking or cycling. Cart House is split into two cottages, so the Left Cart House can also be booked for larger gatherings. FERRY DISCOUNTS AVAILABLE!

ValueLocationLaundry

4.92 out of 5 average rating, 184 reviews

Top Guest favourite

A charming cottage is set against a clear blue sky, featuring a slate roof and multiple windows adorned with shutters. The entrance is approached via a gravel pathway, bordered by shrubs and greenery, leading to a slightly elevated lawn area behind.

Cottage in Isle of Wight

Rural Isle of Wight cottage with indoor pool use

Escape to the Isle of Wight countryside in this peaceful, semi-detached cottage with three bedrooms, a large garden, wood burning stove and views across open fields. Rowborough Cottage is just 300m from our family farm. Guests can enjoy access with two other cottages to farm animals, playground, games room and heated indoor pool (Feb-Oct) - perfect for families seeking a rural break. With EV charging at the farm and plenty of space to unwind, it’s an ideal base for exploring the island.

LocationFamilyAccuracy

4.99 out of 5 average rating, 140 reviews

Guest favourite

The image features two rustic stone buildings surrounded by greenery. A gravel courtyard is visible in front, bordered by a wooden fence. Potted plants add a touch of color, while a tree line provides a natural backdrop to the serene setting.

Barn in Shorwell

Hidden Away Converted Barn Loft in Shorwell

Northcourt Farm is situated in a valley on the edge of chalk down land, surrounded by pastureland and Grade II Listed Parkland, because of its historic link to Northcourt Manor (privately owned). It's home to our horses, dogs and occasionally some sheep. There are just two dwellings on the farm, our farmhouse cottage and The Barn Flat. The Barn Flat would appeal to walkers and cyclists, having access to the Tennyson Trail, with several paths/bridleways running across our farmland.

ValueLocationLaundry

4.88 out of 5 average rating, 136 reviews

Guest favourite

A charming thatched cottage is surrounded by mature gardens and lawned areas. The cottage features multiple windows adorned with vibrant greenery. A blue sky and bright sunlight highlight the serene setting, inviting views of the natural landscape.

Cottage in Ventnor

Breakers Sound - Thatched Cottage with sea views

Breakers Sound is a detached, listed thatched cottage that sits within an acre of mature gardens with stunning sea views across the English Channel from most areas of the property. The historic village of St Lawrence sits within an area of outstanding natural beauty, with coastal and country walks on the doorstep of the cottage and easy access to many of the island's attractions. The vibrant town of Ventnor, with all its amenities, bars and restaurants, is a 5 minute drive away.

ValueFamilyLaundry

4.93 out of 5 average rating, 144 reviews

Top Guest favourite

A charming brick building is seen nestled among lush greenery, with a gravel driveway leading to the entrance. The surrounding countryside features gently rolling hills under a cloudy sky, creating a serene and natural setting.

Cottage in Isle of Wight

Converted barn perfect for families and couples

At the base of Rowridge Valley in the heart of the Isle of Wight countryside. You will find The Piglet, a great place to stay, relax and use as a base to explore the island. A cosy building with a sunny aspect and a private garden to the rear that overlooks the neighbouring countryside. Due to its location most of the island is accessible from here within a short drive. Explore the heritage castles & monuments, the beaches & surf, and family friendly parks throughout the island.

FamilyLocationCheck-in

4.99 out of 5 average rating, 211 reviews

Top Guest favourite

Lush green fields extend towards the horizon, framed by a sturdy tree and fencing. Rolling hills are visible in the distance under a clear sky, creating a serene countryside atmosphere. Sunlight illuminates the landscape, highlighting the vibrant grass and dotted shrubs.

Guesthouse in Isle of Wight

Perfect cycling, walking and star gazing base

Tucked into the heart of an area of outstanding natural beauty, Fircones is a cosy, purpose built holiday cottage which looks out over beautiful farmland towards Hoy Monument. Short drive to some of the islands wonderful beaches. With a comfortable master bedroom with a double bed and twin beds in the second bedroom, Fircones is ideal for families, cyclists, walkers and anyone who enjoys escaping to the country. Short drive to Ventnor, Freshwater and Newport.

ValueLocationWi-Fi

4.98 out of 5 average rating, 316 reviews

Top Guest favourite

The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.

Home in Lepe

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.

ValueLocationCheck-in

4.98 out of 5 average rating, 149 reviews

Top Guest favourite

A bright master bedroom features a spacious bed dressed in a plaid blanket. Natural light floods the room through large windows framed by elegant wooden beams. A cozy ambiance is created by bedside lamps, and doors open to a balcony overlooking greenery.

Cottage in Ventnor

Woodland View

‘Woodland View’ offers a light, airy and modern interior with beautiful wooden beams and floors finished to a very high specification. It is a real ‘home from home’ and has every mod con a family could need to make their stay feel comfortable. Set on a quiet residential road with an area of woodland to the rear. It has views towards the sea enjoying the beauty of the rugged coastline and warm micro-climate of the south of the Isle of Wight.

LocationFamilyIndoor spaces

4.92 out of 5 average rating, 166 reviews

Top Guest favourite

A charming, vibrant green structure is portrayed, featuring a red door and window accents. The building's unique shape is complemented by a round window at the top. A white picket fence encircles the property, enhancing its quaint appearance against the lush greenery.

Place to stay in Isle of Wight

Quirky Converted Scout Hall with sea views

The Scout Hall is full of fun things & interesting artefacts. One of the first Scout Halls anywhere & dating back to 1908, the property has great sea views towards the Needles from the large balcony. The well known local pub, The Wight Mouse is within two minutes staggering distance and the area is criss-crossed with footpaths, with the sea being approx. a 15 minute walk.

FamilyLocationView

4.94 out of 5 average rating, 82 reviews