Family friendly holiday cottages on the Isle of Wight

Family friendly holiday cottages on the Isle of Wight

Family holidays on the island are the kind of adventure that children remember for years to come. Choose your favourite child-friendly cottage and ask us to book the ferry for you so the little ones can start getting excited.Read more

Whether you are escaping for the first time with your newborn or holidaying with the whole tribe, it is great to have your own space and to be able to do things when you want. And family holidays on the Isle of Wight are full of exciting journeys and destinations, with ferry trips (or hovercraft!), days out, beaches and child-friendly attractions. The island has everything you could want or need for time away with family of all ages.

If you're an active family, this little landmass is surrounded by water so watersports abound. If you're all landlubbers and the ferry ride was more than enough floating, island walks are popular and there are plenty of planned routes to help you explore and discover the views.

Being surrounded by sea, fresh fish will be on the menu in many a restaurant and there are plenty to choose from that welcome little ones. There are play parks, theme parks and plenty of places to run around or just sit and picnic so you can have the best family holiday.

We've got 109 holiday cottages that welcome children on the Isle of Wight.

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 109 self catering cottages for a family holiday on the Isle of Wight to show you.

1 Harrow Cottages is a 1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £356

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £356

Mariners Cove is a 1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £390

Mariners Cove

3628

1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.


This charming one bedroom apartment forms part of a country house set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. With everything set o...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £390

Grace Cottage is a 1 bedroom, dog friendly holiday cottage close to the sea near Ventnor, Isle of Wight
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £525

Grace Cottage

4209

1 bedroom, dog friendly holiday cottage close to the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £525

Valdora is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £554 *

Valdora

4959

3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £554 *

Bay View is a 2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £614

Bay View

3902

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £614

Escape Away is a A luxury retreat with private hot tub and use of swimming pool.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

Escape Away

5612

A luxury retreat with private hot tub and use of swimming pool.


New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base you...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

Driftwood is a A dog friendly luxury retreat with private hot tub sleeping 4.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

Driftwood

5613

A dog friendly luxury retreat with private hot tub sleeping 4.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, new to the portfolio this spring and perfect for couples, small families and four-legged companions who lo...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £617 *

House of Logs is a 4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £665 *

House of Logs

4225

4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £665 *

Our guests rate us 4.8/5 on Feefo, the independent review site.

30 Seaview Bay is a 3 bedroom holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £670 *

30 Seaview Bay

3549

3 bedroom holiday cottage near the beach in Seaview, Isle of Wight.


If you're searching for a place to stay by the sea, 30 Seaview Bay could be just the spot. Perched just steps away from the enchanting Seagrove Bay and Seaview Bay, this sunny apar...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £670 *

Forget Me Not Cottage is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £720 *

Forget Me Not Cottage

5167

3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight


Welcome to the delightfully named Forget Me Not Cottage, a charming three bedroom getaway in the pretty coastal town of Bembridge. With its homely interiors and great location, thi...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £720 *

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