Vacation rentals in Chale

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Top-rated vacation rentals in Chale

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Top guest favorite

A scenic view captures a landscape of rolling fields dotted with hay bales, leading towards a cluster of farm buildings. In the distance, the coastline is visible with cliffs and a backdrop of blue sea under a clear sky.

Condo in Isle of Wight

4.98 out of 5 average rating, 120 reviews

Chale Bay Farm - St Catherine's View

St Catherine's View at Chale Bay Farm is a quiet and comfortable two-bedroom/two-bathroom self-catering apartment. The air-conditioned living area features a contemporary open-plan, fully-equipped kitchen with oven, hob, microwave, fridge/freezer, dishwasher and washer/dryer with dining and lounge space, smart TV, Blu-Ray and WiFi. Sleeps up to 4 (or 5 with rollaway-bed or cot) but you can add more space by booking our stand-alone room Tennyson View or one or more of our other main apartments.

Guest favorite

The exterior of the self-contained residence is depicted, featuring a welcoming entrance with a wooden door and a small staircase leading up to it. Lush green grass surrounds the entrance, complemented by a sun lounger and seating area nearby, creating a relaxing outdoor space.

Guest suite in Whitwell

4.88 out of 5 average rating, 118 reviews

Angela’s Retreat: An adorable countryside property

Angela’s Retreat is located in Whitwell on the Isle of Wight, approx 5 km from Ventnor. There are a variety of old stone buildings and it is home to the Isle of Wight’s oldest pub ‘The White Horse’. It is ideally situated for walks, beach days, cycling and fishing holidays. Angela’s Retreat is a self contained residence with its own entrance, small kitchenette, bathroom and 1 bedroom with a double bed and a sofa bed if required. WiFi and SKY are also available, as well as parking for one car.

Guest favorite

An outdoor area is presented with artificial grass, featuring two folding chairs adorned with floral patterns. A charming bathtub is located nearby, flanked by plants and wooden discs that serve as stepping stones. A wooden fence provides privacy while enhancing the serene setting.

Cabin in Whitwell

4.96 out of 5 average rating, 136 reviews

Cosy dog friendly lodge with an outdoor bath

Willow Brook Lodge is a cosy woodland themed lodge set on the bank of a small Brook on the outskirts of Whitwell on the beautiful Isle of Wight.This lodge sleeps two people comfortably with the added bonus of a sofa bed in the living area should a 3rd person come. Guests will receive a welcoming selection of helpful goodies on their arrival. This lodge is ideally situated if you enjoy walking,cycling or just need a relaxing time away. New 2022 we have an outdoor bath. New 2023 we now allow pets.

Guest favorite

The exterior of Milkpan Farm features a charming bungalow surrounded by lush greenery and flowering plants in pots. A gravel driveway leads to the entrance, creating a welcoming approach to the property.

Guest suite in Godshill

4.97 out of 5 average rating, 147 reviews

Milkpan Farm Holidays

Milkpan Farm is situated in Godshill, which we have recently purchased and have refurbished. ** We offer generous discounts on the ferries * It is set in a superb rural location for couples, ramblers, dog walkers and cyclists and a great place from which to explore the Island. The accommodation is self-contained annex with private access and off-road parking. Central heating, Wi-Fi and smart TV are just some of the facilities available. The accommodation is newly fitted to a high specification.

Guest favorite

A serene walkway lined with charming chalets is surrounded by thriving greenery and trees. The space features a smooth stone path bordered by white railings and planters, leading toward a peaceful garden area. Bright sunlight illuminates the scene, enhancing the natural beauty.

Chalet in Niton

4.75 out of 5 average rating, 181 reviews

Squirrels Nook, Westcliff Holiday Chalets

Jon and Elizabeth welcome you to our lovely cosy holiday chalet, located in one of the most tranquil villages on the Isle of Wight. The perfect retreat for couples, walkers and nature lovers looking for a peaceful tech-free getaway. Local village shops, cafes, and two cosy gastro / real ale pubs. 15 minute drive to the Victorian seaside town of Ventnor with lots of places to eat out, the Island's finest butchers, and little shops selling local crafts and produce, records and antiques. No wifi !

Guest favorite

Two lounge chairs sit on a wooden deck overlooking the tranquil sea, with sandy beach visible in the distance. The ocean reflects a clear blue sky, while plants along the railing add a touch of greenery to the serene coastal setting.

Apartment in Isle of Wight

5 out of 5 average rating, 154 reviews

The Ocean Suite, Ventnor Beach (6ft superking bed)

The ultimate in beachfront living, a perfect romantic escape and popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner of 22/23 LUXLife Magazine Awards, Best Luxury 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, 1 south facing for sunbathing, the other perfect for an alfresco breakfast in the morning sun. No pets but baby welcome!

Top guest favorite

Vacation home in Chale

4.93 out of 5 average rating, 130 reviews

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!

Guest favorite

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

4.95 out of 5 average rating, 117 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.

Guest favorite

A charming cottage is set amidst a well-maintained garden, featuring a lush green lawn and various flowering plants. The stone exterior is complemented by wooden accents, and large windows invite natural light. A peaceful environment contributes to the serene atmosphere of the property.

Cottage in Niton

4.8 out of 5 average rating, 109 reviews

Cosy coastal cottage

Recently fully refurbished cottage, re-opened as an airbnb in May 2024. We are situated in the most southerly village on the Island right on the coastal footpath. A beautiful secluded cottage with lovely walks all around us. Ideal for those looking for some peace with the local village just a 5 min walk away and the beach just a 15 min walk. The cottage itself is really comfortable with 100% cotton or linen bedding. Treat yourself with hot tub hire (at an additional cost).

Top guest favorite

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

4.98 out of 5 average rating, 287 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.

Guest favorite

The charming stone facade of the house is framed by lush greenery and colorful foliage. A thatched roof lends rustic character, while windows reveal a glimpse of the inviting interior. A small entrance leads to an outdoor seating area, surrounded by trimmed hedges.

Cottage in Niton

4.86 out of 5 average rating, 139 reviews

Classic Farmhouse nestled in National Landscape

Locks Farm House is a Grade II listed stone build dating back to 1702. It is a traditional long thatch with the roof also covering the former barn. There are two plain beam reception rooms and two double bedrooms, one with an original panel wall. All the rooms look out onto a walled garden and the Downs surrounding the village. The current owners restored the house lovingly using original materials and remain resident in Niton.

Superhost

An outdoor patio area is visible, featuring a small, round table with two chairs set against a quaint stone wall. The surrounding stone cottage walls exhibit rustic charm, framed by greenery and soft sunlight filtering through nearby trees.

Guest suite in Chale Green

4.89 out of 5 average rating, 259 reviews

Stroud Green Farm 17th Century Brew House

Originally a 17th Century Brew House and Dairy located on a ten acre small holding in the village of Chale nestled at the foot of St Catherine's- Down on the South Coast of the Isle of Wight. It is an ideal base for walking and cycling.local pub nearby. And nearest village store 4 miles away