Isle of Wight Holiday Cottages

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Although we've not seen you for a while, we look forward to welcoming you back soon. 

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Isle of Wight Holiday Cottages can be found across the Island, in both coastal and inland locations, and offer great flexibility alongside many of the home comforts that we all know and love. They may also include some luxuries not available at home like hot tubs and swimming pools!

For many the perfect Isle of Wight break represents a traditional cottage in a picturesque location, and for those searching for this there are plenty on offer! One of the reasons holiday cottages on the Isle of Wight offer a perfect escape is that many are located in secluded, rural areas, often as part of working or former farms. Some of these cottages are charming conversions of historic and former working buildings, allowing you to "step back in time" during your holiday.

There are also cottages contained within some of the holiday parks, giving you access to a range of great shared facilities including like eateries, sports facilities, swimming pools, children's areas and entertainment.

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Pet friendly

Luccombe Villa Holiday Apartments occupies a wonderful, quiet position just a short stroll from Shanklin Chine, Rylstone Gardens, Shanklin Old Village and Appley Steps which lead down to Shanklin's sandy beaches and waterfront pubs. The Dairyman's Cottage is a beautiful holiday cottage in the heart of Tapnell Farm which boasts spectacular views over the west of the Isle of Wight towards Tennyson Down and Freshwater Bay. With a range of two, three and four bedroom self-catering accommodation, Island Riding Centre also offers a great range of facilities.

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Cottages near the beach

With its long, south-facing veranda, the Pavillion Cottage, Osborne is the perfect place to stay. It’s easy to agree with Queen Victoria, who said: 'It is impossible to imagine a prettier spot'. The Old Club House is a quirky holiday cottage has views across St Helens Duver. The local sandy beach is within a few minutes walk which is perfect for a swim. Sea Shells by the Beach is a wing of Sea Shell House that has been renovated to a very high standard to provide beautiful accommodation for six people in three bedrooms.

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Luxury cottages

Whether you are looking for blissful relaxation to unwind and restore a sense of wellbeing or for a family holiday packed with fun and activities, a break at The West Bay Club & Spa is the perfect coastal getaway. Willses Bed & Breakfast and Self Catering is a beautifully restored Grade II listed thatched cottage dating back to the 17th Century, located in the historic village of Brighstone. Awarded a Gold 5* rating by the Tourist Board, Yafford Mill Barn has been designed to provide light and spacious accommodation to the highest standards for six people.

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Cottages with a hot tub

The Bay Colwell is situated on the beautiful west coast of the Isle of Wight and just a short stroll from the wonderful Colwell Bay beach and features an indoor heated swimming pool and tennis court. Whitecliff Bay Holiday Park offers gorgeous self-catering accommodation in their Jolly Nice Chalets - warm, comfortable and bright, these vibrant apartments make for a relaxing, family orientated place to stay. Woodside Coastal Retreat is a tranquil and relaxing holiday resort which offers stunning views of the north east coast of the Island, - located between Cowes and Ryde, this is the perfect destination for a self-catering holiday on the Isle of Wight.

All cottages with a hot tub

Cottages with a swimming pool

Set in 23 acres of beautiful parkland, Rookley Park features a wide range of activities for the whole family, as well as being a great place to relax. Appuldurcombe Gardens Holdiay Park is situated within an Area of Outstanding Natural Beauty (AONB), making it a perfect base for walkers and cyclists, as you can access many walkways within minutes. Situated on the edge of Newtown Estuary; a designated National Nature Reserve, Shalfleet Manor is a beautiful 17th century Manor, comprising Manor House, three bedroom barn and separate four bedroom farmhouse. Enjoy activities such as birdwatching, canoeing and paddle-boarding from the manor.

All cottages with a pool

Cottages with a sea view

Set in the Undercliff Area of Outstanding Natural Beauty, Woodcliffe Holiday Apartments & Cottage stands in peaceful secluded terraced gardens - the house, cottage and modern apartments face south, offering superb views of the English Channel. Waters Edge comprises three double bedrooms with three bathrooms arranged over three floors, twenty five metres from the sea shore and just ten minutes walk away from the historic harbour town of Yarmouth. The Sea House is a spectacular four bed luxury new build house on the seafront of Seagrove Bay, Isle of Wight that can sleep eight.

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Cottages near a pub

Longwood Edge is a beautiful detached cabin style bungalow with stunning sea views situated in the much sought-after hamlet of Bonchurch, and just 150 yards away from the popular Bonchurch Inn. A thoughtfully remodelled two bedroom detached bungalow, Windward is in the centre of Yarmouth with parking at the front. Firefly House is a luxury Victorian house with 2 parking spaces, just a few minutes walk from the historic town centre, waterfront and marinas of Cowes.

All cottages near a pub

Family friendly cottages

The charming Mill Cottages are tucked away within the grounds of one of the Island’s popular family attractions, Calbourne Water Mill, and set in 10 acres of landscaped gardens. Upper Chine Holiday Cottages & Apartments were previously a Private Girls School, built in 1928, and the site offers original stone buildings which have been sympathetically renovated to form several self-catering units. Boniface Lodge is a spacious villa with many beautiful Edwardian features but in a modern, comfortable setting and the cliff path at the end of the road has panoramic sea views.

All family friendly cottages

Group friendly cottages

Tapnell Manor is set between two working dairy farms. With views to Tennyson Down and the Solent you will find yourself surrounded by natural beauty and grazing cows. Marine Villa, The Art Deco House is a wonderful original ArtDeco house built in 1929 and which over looks Sandown Bay on the Isle of Wight. Holidays on The Garlic Farm have seven beautiful self-catering cottages and three luxury yurts on the Garlic Farm sleeping between two and ten people.

All group friendly cottages

Self-catering agencies

Created over 40 years ago, Classic Cottages are independent holiday cottage specialists, still run and owned by the founding family, who pride ourselves on their local expertise. Island Cottage Holidays have been offering cottage holidays on the Isle of Wight for over 25 years and has an enviable selection of over 130 quality properties in rural and coastal locations. With ten years of experience and many returning customers, Wight Coast Holidays have a range of great holiday homes for you to choose from.

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Cottages in the country

Nettlecombe Farm is a working farm that offers luxurious self-catering holiday accommodation nestled in the heart of the rolling South Wight countryside, half a mile from the village of Whitwell. Brook House Cottage - The Old Coach House offers style, charm and character - as well as comfort and all the essentials that you will need for a wonderful holiday on the Island. Haddon Lake Boathouse is tucked away in the glorious 2-acre grounds of Haddon Lake House, voted one of the country’s finest gardens in the television series 'I Own Britain’s Best Home & Garden'. Perfectly located at the Gateway to Freshwater Bay and nestled alongside the Afton Nature Reserve, Little Sedge self-catering holiday accommodation offers short or longer breaks for walking, cycling or simply enjoying the breath-taking views of this beautiful Island.

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