Vacation rentals in Chale

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Top-rated vacation rentals in Chale

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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!

4.99 out of 5 average rating, 180 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.

4.98 out of 5 average rating, 120 reviews

Top guest favourite

Vacation 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!

4.92 out of 5 average rating, 184 reviews

Top guest favourite

A view from the cabin captures lush greenery and colorful flowers leading down to the village below. The open sea glistens in the distance, framed by trees and rooftops. A clear blue sky enhances the scenery, offering a sense of tranquility and natural beauty.

Guesthouse in Ventnor

Beautiful Cabin with spectacular sea views & deck

Enjoy peace and tranquility in this comfortable spacious Cabin located in the owner's beautiful garden. Kingsize bed with luxury bedding, fully fitted kitchen and bathroom. Dining table and large comfortable sofa, with 2 sets of doors leading to private deck and spectacular sea views. Private access at the rear of the plot for free parking. You will need a torch after dark, and please note the plot is steep. Cabin equipped with superfast broadband. *Ask me about Ferry discount vouchers*

4.96 out of 5 average rating, 114 reviews

Top guest favourite

A cozy sitting room features a comfortable sofa, decorative cushions, and a log burner set in the stone fireplace. Natural light fills the space through two windows, with a small dining table and a television positioned nearby. Sunlight casts soft shadows, enhancing the room's inviting feel.

Cottage in Whitwell

Hedgerow Cottage (Berryl farm Cottages)

Hedgerow Cottage is in a row of 4 idyllic stone cottages, in an area of outstanding natural beauty. Surrounded by fields in the hamlet of Berryl, but under a 10 minute walk to the village pub. Complete peace with only the sound of the birds and Cows! 2 miles to stunning national trust coastline and swimming beaches. A perfect base to explore the Island. Dog friendly, adult only. Generous ferry discounts available. If unavailable, please see our other listings for the neighbouring cottages.

4.97 out of 5 average rating, 164 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.

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.

4.93 out of 5 average rating, 144 reviews

Superhost

A spacious living area features a soft rug and comfortable seating, with light filtering through large glass doors. Outside, a wooden dining table is set for al fresco meals amidst a lush garden, inviting a serene and relaxed dining experience.

Home in Niton

Cherrydale Cottage - Semi Rural Family Retreat

Are you are looking for both peace and quiet and access to local amenities? Well you have found it here :-) Cherrydale is set in a quiet cul-de-sac on the edge of the village, backing onto fields. This is the ideal base to explore the Island. Heading out from this tranquil home, you are never far from beautiful beaches, cycling routes, scenic coastal roads, excellent walks and an array of pubs and restaurants. We provide ferry discounts with booking confirmation.

4.84 out of 5 average rating, 100 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.

4.98 out of 5 average rating, 316 reviews

Top guest favourite

A bright living space is showcased through large glass doors, offering a view of shimmering waves. A vase of white flowers is prominently displayed on a wooden table, contrasting with a soft grey sofa in the background, creating a serene atmosphere.

Condo in Ventnor

Modern Beach Side apartment with easy access.

“Beach Side” is a modern apartment directly on the seafront of the popular seaside resort of Ventnor. Located on the south coast of the Isle of Wight, Beach Side is the perfect location to enjoy a beach holiday in one of the sunniest places in the U.K. and as a base to explore the rest of our beautiful Island. Beach Side is on the ground floor of a small block of newly built apartments and so offers easy, no step, access directly onto Ventnor Seafront.

4.91 out of 5 average rating, 255 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.

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.

4.92 out of 5 average rating, 166 reviews