Holiday rentals in Chale

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Top-rated holiday rentals in Chale

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Guest favourite
Flat in Isle of Wight
4.99 out of 5 average rating, 170 reviews

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!

Top guest favourite
A charming courtyard is framed by vibrant purple wisteria hanging from a pergola. Two wooden lounge chairs are positioned to receive sunlight, surrounded by potted plants and lush greenery. The entrance to the cottage is visible, welcoming guests to a tranquil outdoor space.
Cottage in Isle of Wight
4.99 out of 5 average rating, 189 reviews

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres

This accommodation has been specifically designed for couples looking for a tranquil break where quality and attention to detail are important factors. Ideal for romantic breaks or special occassions, surrounded by open countryside with an abundance of wildlife right outside your door. The quiet yet accessible location is a few minutes drive from various beaches perfect for cycling, walking, nature watching and exploring the IOW. See "Other details" for ferry discounts. EV charging at 40p KWH.

Top guest favourite
Guest suite in Isle of Wight
5 out of 5 average rating, 135 reviews

Sail Away - Ventnor apt with spectacular seaviews

Situated overlooking Ventnor with uninterrupted views of the English Channel. A bright, airy, and fully equipped one bedroom apartment with a private entrance and a small balcony area. Watch the Sun and Moon rise over the sea, see the fishing boats and cruise ships sail by, and if you're really lucky, you might spot a pod of dolphins swim past. On a dark night, you can see the Milky Way light up the sky. 20 minutes stroll to Ventnor beach and High Street with its independent and artisan shops.

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.
Apartment in Isle of Wight
4.97 out of 5 average rating, 108 reviews

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.

Top guest favourite
Barn in Isle of Wight
4.97 out of 5 average rating, 241 reviews

Little Wing peaceful barn with garden/parking

Little Wing is a beautifully converted studio apartment (originally a milking parlour for goats) located in a peaceful, rural village- 'Best Kept Village' on Isle of Wight 2025 - in the heart of an Area of Outstanding Natural Beauty. Including a large, super-king size bed, the open plan contemporary design is perfect for couples looking for a quiet or romantic retreat and the patio and private garden are perfect for summer relaxation, while underfloor heating means even winter days are cosy!

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.
Guest house in Isle of Wight
4.95 out of 5 average rating, 104 reviews

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*

Top guest favourite
A lush garden scene features a flourishing tree with vibrant green leaves in the foreground, set against the rustic stone barn's weathered exterior beneath a clear blue sky. The well-maintained grass invites relaxation amid the surrounding greenery and blooming foliage.
Home in Chale
4.96 out of 5 average rating, 120 reviews

Gotten Manor Estate - The Milk House

A peaceful, remote 200-year-old stone barn set within the Gotten Estate, with three bathrooms that sleeps 6/7, with wonderful views of the countryside and sea. At the end of a country lane, we are tucked below the Hoy Monument at St Catherine's Down, a mile inland from the coast, with amazing dark skies, an abundance of wildlife and amazing coastal walks or bike rides on your doorstep. We are a wild and idyllic getaway in the most beautiful part of the island. FERRY DISCOUNTS AVAILABLE!

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 Isle of Wight
4.93 out of 5 average rating, 132 reviews

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.

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
4.98 out of 5 average rating, 193 reviews

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.

Top guest favourite
The exterior of a modern wooden barn structure is visible, characterized by a sloping grey roof and large windows. A gravel driveway leads to the entrance, with a manicured green lawn surrounding the building. A parked car is nearby, along with a tree providing natural shade.
Barn in Isle of Wight
4.99 out of 5 average rating, 158 reviews

Meadowview Barn

Enjoy sole use of this charming detached oak barn, with its upper floor recently converted into a spacious apartment. Nestled in 30 acres of stunning private grounds and countryside, perfect for peaceful walks on/off site. Super-king bed, view French doors, kitchenette, Smart TV with surround sound, pool table, table tennis, outdoor seating & BBQ. Pubs & beaches within walking/short drive. Wi-Fi, parking included. Pet-friendly on request. Ferry discounts available enquire!

Top guest favourite
An outdoor dining area features a stylish table set with drinks and refreshments. Comfortable chairs surround the table, which has a glossy surface reflecting the clear blue sky and distant sea views. The surrounding trees provide a serene backdrop.
Home in Isle of Wight
4.97 out of 5 average rating, 111 reviews

Longwood Edge, a dream home by the Sea

This stylish, spacious, ‘State of the Art’ home is perfect for those looking for a luxurious, relaxing break in a tranquil coastal location. With a large open plan living/dining area, fully equipped kitchen with breakfast island, 3 large bedrooms and 2 luxurious bathrooms. Located on a quiet road 100 yards from the award winning Bonchurch Inn, you can relax, stay at home or wander into Ventnor with its variety of restaurants. We provide discounted ferry travel on booking.

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.
Guest house in Isle of Wight
4.98 out of 5 average rating, 299 reviews

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.

Popular amenities for Chale holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Isle of Wight
  5. Chale