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Luxury Holiday Homes & 5 Star Cottages

25 Isle of Wight holiday cottages with 4 Star Gold Award, 5 Star and 5 Star Gold Award tourist board gradings.

You can find out more about the Gold Award below these cottages.

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

4

Sleeps 4 in 2 bedrooms
Built of Island Stone and the building dates back to 1695. It is one of a pair of cottages divided by an impressive central arch leading to an inner courtyard with pretty gardens and four additional cottages. The cottage is very pleasantly situated in a quiet hamlet in attractive countryside.

Dairymaid Cottage self catering cottage Shanklin, Isle of Wight

Shanklin, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

4

Sleeps 4 in 2 bedrooms; Children 5 + welcome
This delightful Grade II listed stone cottage has been sympathetically converted from the former stables of the nearby Apse Manor. It nestles within an enclosed courtyard approached through a lovely large arched entrance. The original building dates back to 1695, and period stone door surrounds and lintels can be seen on its south elevation. Deceptively spacious, Groom Cottage has thick stone walls, wooden beams and an attractive appearance with four gables.

Groom Cottage self catering cottage Shanklin, Isle of Wight

Shanklin, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

4

Sleeps 4 in 2 bedrooms; Children welcome
Honeymoon Cottage stands towards the end of a country lane beside a small farm. It is in an ‘Area of Outstanding Natural Beauty' on the edge of the rural village of Whitwell close to the south coast of the Island. This is a wonderful walking area with footpaths leading directly from the cottage into the beautiful countryside and on to the downs.

Honeymoon Cottage self catering cottage Whitwell, Isle of Wight

Whitwell, Isle of Wight

WiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

4

Sleeps 4 in 2 bedrooms; Children 12 + welcome
The Granary is a charming cottage, which has been carefully converted from the wing of a large ancient barn dating back to the 17th Century - Ningwood Green Barn. It is nestled in lovely peaceful West Wight countryside and has views across the surrounding fields to the downs. This is a lovely walking area and is not too far from the coastal path.

The Granary self catering cottage Yarmouth, Isle of Wight

Yarmouth, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

5

Sleeps 5 + baby in 3 bedrooms
This wonderful property occupies a delightful location in the extensive grounds of Yafford Mill, an 18th century restored mill, set amidst the beautiful countryside of the coastal area of south west wight. This is ‘An Area of Outstanding Natural Beauty’. The quiet and unspoilt beaches of Brighstone and Brook are within a 5 minute drive.

Yafford Mill Barn self catering cottage Yafford, Isle of Wight

Yafford, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

6

Sleeps 6 in 4 bedrooms; Children welcome
This lovely detached house is very attractively situated, close to the cliff top above Totland Bay, on the west side of the Island. There are sea views from the rooms at the front of the house and the lighthouse at Hurst Point can be glimpsed in the distance. The sandy bay of Totland where swimming, paddling and boating can be enjoyed is only a 3 minute walk away. This is also a marvellous walking area.

Chine Cottage self catering cottage Totland Bay, Isle of Wight

Totland Bay, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

6

Sleeps 6 in 3 bedrooms; Children welcome
High Rising is situated within a few minutes walk of the sea at Gurnard. Here there is a quiet beach where visitors can enjoy paddling swimming and boating. A pleasant café and nearby public house provide refreshments. There is easy access to the west side of the Island with its quiet sandy coves and the nearby National Nature reserve of Newtown – an area of outstanding Natural Beauty and a wonderful area for walking and bird watching.

High Rising self catering cottage Gurnard, Isle of Wight

Gurnard, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

6

Sleeps 5 + 1 in 3 bedroom; Children welcome
This lovely thatched cottage dates back to 1701. It is full of character with exposed beams, inglenook fireplaces. It stands in ‘An Area of Outstanding Natural Beauty' with views of Brighstone Downs. The pretty village of Brighstone village with its tea rooms, public house and village shops is within a 15 minute stroll. The cottage is only a mile from the coast and here there are several quiet sandy coves.

Old Rock Cottage self catering cottage Brighstone, Isle of Wight

Brighstone, Isle of Wight

Pets welcome Self Catering Holiday Home Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

6

Sleeps 6 in 3 bedrooms; Children welcome
Situated within a few minutes walk of the centre of the pretty village of Shalfleet on the west side of the Isle of Wight. The village has a lovely 12th century church, its own village shop and a public house which is extremely good for meals. There is a tennis court which visitors are welcome to use and also an attractive heated swimming pool.

Shalfleet Manor Barn self catering cottage Shalfleet, Isle of Wight

Shalfleet, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

6

Sleeps 6 in 3 bedrooms; Children welcome
The Old Cottage is a wonderful 18th Century, Grade 2* listed property. It is beautifully situated overlooking the sea, in ‘ An Area of Outstanding Natural Beauty', on the south coast of Island. A quiet cove, where visitors can paddle and swim, is within a 15 minute walk of the cottage. St Lawrence is renowned for its mild climate and in the nearby Botanical Garden many rare and tropical trees and plants are grown.

The Old Cottage self catering cottage St Lawrence, Isle of Wight

St Lawrence, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

7

Sleeps 6 + 1 in 4 bedrooms
This lovely stone cottage is situated in the small rural hamlet of Bowcombe which stands between the pretty village of Shorwell and Carisbrooke with its medieval castle. Shorwell and Carisbrooke are both within a 5 minute drive and have public houses which are good for meals. The cottage offers easy access to the small bays and coves on the south west side of the Isle of Wight. The larger sandy beaches of Ventnor and Shanklin are within a 20 minute drive.

Bramble Cottage self catering cottage Newport, Isle of Wight

Newport, Isle of Wight

Pets welcome Self Catering Holiday Home Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

7

Sleeps 6 + 1 in 3 bedrooms; Children welcome
This lovely stone cottage is built of Isle of Wight Stone and has been converted from an ancient stone barn. Byre Cottage is situated in a small country lane in attractive countryside. This is a lovely walking area and footpaths lead from close to the cottage to the beautiful downs above Ventnor. Byre Cottage is only 1.5 miles from the centre of the seaside town of Shanklin with its wonderful sandy beach which is popular for swimming and paddling. The neighbouring seaside towns of Sandown and Ventnor are within a 10 minute drive.

Byre Cottage self catering cottage Shanklin, Isle of Wight

Shanklin, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

7

Sleeps 6 + 1 in 3 bedrooms
This attractive New England Style property stands on high ground in a small rural hamlet on the south west coast of the Island and enjoys spectacular views of the sea. A lovely quiet beach where visitors can paddle and swim is only a 3 minute walk away. This is ‘An Area of Outstanding Natural Beauty' and there are wonderful walks from the cottage, with the coastal path only a stones throw away. The picturesque village of Brighstone with its thatched cottages, public house, restaurant and tea shop is within a 10 minute walk.

November Cottage self catering cottage Brighstone, Isle of Wight

Brighstone, Isle of Wight

Pets welcome Self Catering Holiday Home Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

7

Sleeps 6 + 1 in 3 bedrooms; Children welcome
This delightful detached property is set in its own grounds in an attractive semi rural area within 5 minutes walk of the beach and within a 10 minute stroll of the small coastal town of Yarmouth – a small port on the west side of the Island, renowned for sailing. Yarmouth has a variety of small shops, public houses, tea shops and restaurants. The sandy coves of Totland and Colwell Bay are only a few minutes drive away.

Treetops self catering cottage Yarmouth, Isle of Wight

Yarmouth, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

7

Sleeps 7 in 4 bedrooms, Children Welcome
This picturesque Grade II listed cottage dates back to 1676 and is attractively situated at the end of a quiet lane with a lovely ford and footpath leading to the nearby medieval castle of Carisbrooke. Located in the oldest part of Carisbrooke village which is a conservation area lying within ‘An area of Outstanding Natural Beauty'. The castle is only 5 minutes walk away and can be glimpsed from the garden and main bedrooms. This is a wonderful walking area as within 5 minutes walk of the cottage visitors can join the famous Tennyson Trail which follows the downs westerly towards The Needles.

Virginia Cottage self catering cottage Carisbrooke, Isle of Wight

Carisbrooke, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

8

New Cottage; Sleeps 7 + 1 in 4 bedrooms
This elegant Victorian Villa is situated close to the centre of the attractive coastal town of Yarmouth and is within a few minutes walk of the beautiful River Yar and wonderful walks. The town is a fashionable sailing centre with a good variety of restaurants, public houses and small interesting shops. The sandy bays of Colwell and Totland are within a 5 mintue drive. Belmont Villa has a lovely large fenced garden and private parking.

Belmont Villa self catering cottage Yarmouth, Isle of Wight

Yarmouth, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

8

Sleeps 8 in 4 bedrooms; Children welcome
This spacious house is splendidly situated immediately beside the sea. A stroll across the lawn leads to the beach where swimming, beach sports and boating can be enjoyed. A yacht can also be privately moored. There are spectacular, and panoramic sea views from the main rooms in the house and from the garden. Bonny Blink is in the quiet seaside village of Seaview on the east side of the Isle of Wight, commanding views across the Solent and the open sea. The pleasant village centre with its shops, post office and restaurants is less than a five minute walk away.

Bonny Blink self catering cottage Seaview, Isle of Wight

Seaview, Isle of Wight

Seaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
0 Star Self Catering Isle of Wight Holiday Cottage

8

Sleeps 8 in 4 bedrooms
Greenside is very pleasantly situated in a quiet,prestigious residential area of Cowes. There are open views from the rear of the house across the golf course. It is less than half a mile from the beach at Gurnard. The centre of Cowes is a 15-minute walk from the house.

Greenside self catering cottage Cowes, Isle of Wight

Cowes, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

8

Sleeps 8 in 4 bedroom; Children 5+ welcome
Spring Cottage stands in an idyllic location, within a 2 minute walk of the beach in the pretty seaside village of Bonchurch on the south east coast of the Island. The cottage enjoys beautiful sea views from most rooms and from its enchanting garden. Bonchurch is a peaceful village with a small shop, public house, good restaurant and two ancient churches plus a pretty pond which is home to carp, ducks and a variety of birds.

Spring Cottage self catering cottage Bonchurch, Isle of Wight

Bonchurch, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

8

Sleeps 8 + 2 (1 child on folding bed and 1 baby in cot) in 4 bedrooms; Children welcome
This lovely old farmhouse is very attractively situated in peaceful countryside within a 5 minute drive from the market town of Newport with its various shops and the medieval castle of Carisbrooke. The lovely central position of this property makes it ideal for touring the Island as most parts can be reached within a 30 minute drive. The beautiful sandy beaches of Sandown and Shanklin are only a 20 minute drive away.

Stone House self catering cottage Blackwater, Isle of Wight

Blackwater, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

8

Sleeps 8 in 4 bedrooms; Children welcome
This wonderful detached property stands in a superb position beside the sea, close to the centre of Cowes. It enjoys panoramic sea views from almost every room. The glass walls, balconies and large open terraces of the house enable visitors to relax, enjoy meals and awake to the sight of the sea.

The Glass House self catering cottage Cowes, Isle of Wight

Cowes, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightPets welcome Self Catering Holiday Home Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
4 Star Self Catering Isle of Wight Holiday Cottage

10

Sleeps 7/8 + 2 in 4 bedrooms
This lovely stone cottage is beautifully situated in a small hamlet, on the south west coast of the island, amidst a wonderful rural and coastal landscape. The cottage is within a 2 minute walk of the delightful beach at Brook where visitors can paddle and swim. This is ‘An Area of Outstanding Natural Beauty’ with much of the area protected by the National Trust.

Greystone Cottage self catering cottage Brook, Isle of Wight

Brook, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

10

New Cottage; 5 Stars; Sleeps 10 in 7 bedrooms
Orchard Bay House is a unique and absolutely wonderful property with stunning sea views from all of the main rooms. The house stands in an idyllic position, being the sole property on the beach of Orchard Bay - a small secluded cove on the south coast of the Isle of Wight.

Orchard Bay House self catering cottage St Lawrence, Isle of Wight

St Lawrence, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightSeaside Self Catering Holiday Cottage near the beach Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

10

Sleeps 10 in 5 bedrooms;
This wonderful property stands beside the beach in Seaview – a small prestigious resort renowned for beach holidays, sailing and boating. It provides a destination for many discerning families who return year after year. The Beach House has a prime & peaceful position which enjoys panoramic sea views from most rooms. A stroll across the garden leads to a gateway providing direct access to Seagrove Bay and visitors can relax on the balcony and watch the children playing on the beach.

The Beach House self catering cottage Seaview, Isle of Wight

Seaview, Isle of Wight

Gold Award Self Catering Holiday Cottage Isle of WightWiFi internet Self Catering Holiday Cottage Isle of Wight
5 Star Self Catering Isle of Wight Holiday Cottage

11

Sleeps 11 in 5 bedrooms;
A delightful detached house with a private heated swimming pool set in extensive private grounds and with coastal views from all the front facing rooms. It is very attractively situated in the small rural hamlet of Limerstone and is only 1.5 miles from the south west coast of the Isle of Wight. This is an area of outstanding natural beauty. There is access to a wonderful walking area with footpaths following the downs at the rear of Monkspath on the Worsley / Tennyson Trial towards the Needles.

Monks Path self catering cottage Limerstone, Isle of Wight

Limerstone, Isle of Wight

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Gold Award Self Catering Isle of WightWhat is the Gold Award?

In the words of VisitEngland, who give the award,"[Gold Awards] are given in recognition of exceptional quality within a property's star rating, or for outperforming a star rating".

We are proud to have a large number Gold Award holiday cottages on the Isle of Wight and some extremely prestigious 5 Star Gold Award properties as well.

For more information about the Gold Award visit VisitEngland

If you are looking for 5 Star self catering holiday cottages on the Isle of Wight visit our 5 Star Self Catering page.

Luxury Isle of Wight Self Catering Holiday Home Map