Our pick of the top Isle of Wight cottages for 2020


Posted by Ruth on 2nd July 2020

Isle of Wight

The Isle of Wight is a fantastic destination to visit all year round and, as it’s accessed by a short ferry crossing, it gives the feeling of a foreign holiday with the ease of a UK staycation. With so many beautiful beaches, historic sites and nature-rich landscapes to explore, whatever you want from island life, you’ll be able to find it here. Discover the Isle of Wight in our guide to find out more!

Our range of Isle of Wight cottages is equally as diverse – from huge homes close to the coast perfect for big celebrations, to cute cottages nestled in the countryside ideal for a romantic bolthole. To help you find your dream setting for the most memorable of Isle of Wight holidays, we’ve rounded up our top Isle of Wight cottages for 2020.

Including cottages with hot tubs, dog-friendly properties and luxury homes, browse our top 10 cottages and find some inspiration for your next Isle of Wight holiday. 

All Isle of Wight cottages

One of the best family-friendly cottages on the Isle of Wight

Reeth Cottage

Reeth Cottage, Ventnor | sleeps 6

This family-friendly home is sure to please every member of your family, with plenty of space to spread out, relax and cherish this special time together. Kids will love the outdoor play equipment in the large grassy garden, including a trampoline, swings and a slide, while the bunk bedroom creates a fun sleepover atmosphere. Gather all together over a BBQ in the lovely garden, or on cooler nights you can snuggle up in front of the wood burner on the plush sofas and watch a family film on the TV.

What the property manager says:

“Surrounded by countryside, this cottage is positioned within a stunning walking and cycling area in the heart of Niton. There really is something for everyone here with a stylish interior and wood burner for the grown ups, and a magnificent play area outside for the children with swings, a trampoline and a slide. This is the perfect place to make some life-long memories together.”

More family-friendly cottages

One of the best dog-friendly cottages on the Isle of Wight

Dairymaid Cottage

Dairymaid Cottage, Shanklin | sleeps 4 + 3 dogs

Welcoming three dogs with a special welcome hamper, this property is sure to set tails wagging. Four-legged guests will be in their element with an enclosed garden to zoom around, a dog-friendly beach close by and a roaring wood burner for naps when the day is done. For humans, this Grade II-listed home has been furnished in calming and rustic neutral tones and has a tranquil garden with lots of spots for sitting in the sun, creating the perfect relaxed atmosphere for a peaceful holiday.

What our guests say:

This property was everything that we wanted in a quiet location. Very well appointed with a lovely welcome hamper for both us and the dogs.” – Martyn, 2019

More dog-friendly cottages

One of the best sea-view cottages on the Isle of Wight

Sea Shells By The Beach

Sea Shells By The Beach Cottage, Bonchurch | sleeps 6 + 2 dogs

With a spectacular position right on the water’s edge, this is one of the finest Isle of Wight holiday cottages if you’re looking for awe-inspiring sea views. The coastal vista is best enjoyed from the private walled and fenced garden which has a beachy atmosphere, complete with deckchairs and parasols. However, the sea can be spied from most of the rooms indoors too, which are mainly decorated in relaxed white tones, perfect for long, lazy days relaxing with loved ones by the coast.

What our guests say:

Thank you so much for welcoming us to this house. It is an absolutely gorgeous place and we've loved our stay, waking up right next to the sea. This has been the first time we have stayed here and it’s been wonderful. It feels so homely whilst looking immaculate at the same time.” – Cain, 2019

More sea-view cottages

One of the best celebration cottages on the Isle of Wight

Bonny Blink Cottage

Bonny Blink Cottage, Seaview | sleeps 10

There couldn’t be a more spectacular setting for a big celebration than this huge home, right on the seafront in the appropriately named Seaview. Boasting five huge bedrooms and plenty of reception rooms, there’s lots of space for everyone to spread out. Come together to celebrate around the indoor dining table or take in the views from the impressive decked area, the perfect spot for extra-special drinks and a BBQ to get the party started.

What our guests say:

The most amazing views from the back with just incredible sunrises. We had a wonderful family seaside holiday, would love to go again!” – Gloria, 2019

More large cottages

One of the best Isle of Wight cottages with a hot tub

Yew Tree House

Yew Tree House, Parkhurst Forest | sleeps 6 + 2 dogs

Nothing beats relaxing in your very own hot tub while on holiday, and this property can certainly deliver that dream! With a hot tub available in the summer months, it’s one of our favourite Isle of Wight holiday cottages for a totally tranquil break, as it’s also surrounded by beautiful gardens on the edge of Parkhurst Forest. Spend an evening enjoying the peace and quiet while having drinks outside before slipping into the bubbling tub for the finishing touch to a decadent and relaxing holiday.

What our guests say:

It is in the perfect location to explore the whole island. We had everything we needed at the cottage with a very well-equipped kitchen. The hot tub went down a treat! The garden is great for kids.” – Nicola, 2019

More hot tub cottages

One of the best Isle of Wight cottages by the beach

The Sea Terrace Cottage, Shanklin | sleeps 6

If you’re looking for Isle of Wight cottages to rent that are close to the island’s many beaches, well, you can’t get much closer than at this serene home. It’s a mere stone’s throw from one of the Isle of Wight’s most popular beaches, Shanklin, and also boasts sea views from many of the rooms, creating a laidback ambience throughout. Return from a day combing the sandy shores to relax on one of the decked terraces, then drift off in the plush super-king-size bed listening to the sound of the waves lapping the sands.

What our guests say:

Great views. Beautifully clean. Owners have thought of everything – just like a home from home but right on the beach.” – Andrea, 2019

More coastal cottages

One of the best remote cottages on the Isle of Wight

Upper Dolcoppice

Upper Dolcoppice Farmhouse, Whitwell | sleeps 9 + 5 dogs

Surrounded by 33 acres of wildlife-rich land, this farmhouse is just the antidote to a hectic life and is one of our favourite remote holiday homes on the Isle of Wight. The property enjoys a garden that is 1.5 acres which creates a tranquil environment for you, your guests and the five dogs that are allowed at this property to explore. Inside, you’ll find calming tones and ample space to relax, with plenty of countryside views to be admired from most of the windows.

What our guests say:

If you like the feel of isolation and love the quiet, this is the place for you. The gardens are fabulous and dog safe. The surrounding fields wonderful for exploring. We didn't want to leave.” – Karen, 2020

More remote cottages

One of the best luxury cottages on the Isle of Wight

Haviland Cottage

Haviland Cottage | sleeps 7 + 2 dogs

This elegant period cottage will delight you from room to room, with no attention to detail spared throughout its fantastic refurbishment. It’s a wonderful location for an indulgent multi-generational holiday with something to please each member of your party; kids will love exploring the secret gardens while grown-ups can soak in the hot tub or doze in the four-posted bed – and dogs even have their own bedroom! Later on, gather together in the refined conservatory for a special meal with all your favourite people around you.

What our guests say:

This property is a real gem, with Its beautiful landscaped gardens, spacious accommodation, top-end furnishings and equipment, it really is a five-star property. Having stayed in a number of holiday lets, this is simply the best!” – Roy, 2020

More luxury cottages

One of the best quirky Isle of Wight cottages

Castle Coach House final

Castle Coach House, Ventnor | sleeps 2

This truly unique converted stable has surprises at every turn, from the distinctive façade to the jewel-toned décor through the interior. The antique furniture and charming ornaments inside create character, and there’s plenty of room to relax, whether it be in the opulent lounge in front of the feature fire or in the luxurious free-standing bath in the spacious bathroom. If you want to venture out, the centre of Ventnor can be reached via a short walk on the picturesque coast path.

What our guests say:

We enjoyed our stay in this quirky, historic cottage and especially appreciated the lovely comfy bed and luxurious roll-top bath.” – Joanne, 2019

More quirky cottages

One of the best romantic Isle of Wight cottages

Moonfleet Cottage

Moonfleet Cottage – Freshwater | sleeps 2 + 1 dog

Whisk your loved one away for a break where you can press pause on life and spend quality time together, just the two of you. This romantic cottage is perched in a private location on a clifftop on the Isle of Wight’s west coast, giving you gorgeous sea views and plenty of fresh coastal air, as well as the opportunity for a morning dip in the bay below. On chilly days, snuggle up inside in front of the wood burner and, if the sun shines, you can take a glass of something special out to the chairs in the garden and drink in the views.

What our guests say:

Moonfleet Cottage is beautiful and characterful in the most stunning location. Stepping out in the morning, taking a deep breath of fresh air on the cliff overlooking the sea is priceless. It's cosy inside, bed very comfy. Very small but everything there you need. Walks right from the doorstep, no traffic at all. Peace and quiet.” – Kerstin, 2020

Stay with us on the Isle of Wight

If you still haven’t found the perfect holiday cottage, then take a look at our brilliant collection of Isle of Wight self-catering accommodation. Ranging from large holiday lets for big celebrations to bijou villas for romantic getaways, and many boasting countryside or coastal views, we have plenty of properties for you to browse through below. 

All Isle of Wight cottages

Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.