Luxury Cottages for 4 People on the Isle of Wight

Enjoy a luxury island retreat and book a holiday cottage for up to four people on the Isle of Wight. There's room for you and three of your nearest and dearest, and many of our cottages are dog-friendly too. Browse through our selection of 145 available self-catering cottages and take a step closer to the holiday of a lifetime.Read more

Spending time with our friends and family is really important, but it's not always that easy to get together and catch up. Holiday cottages provide great neutral ground in beautiful settings, away from the distractions of everyday life. Spend time together in a luxury self catering cottage sleeping up to 4 people and rediscover yourselves.

Self Catering Cottages on the Isle of Wight for Four People

At Classic Cottages we pride ourselves on marketing only the finest holiday cottages on the Isle of Wight. Each one of our self catering cottages is personally inspected and fully equipped to ensure your total comfort. Take your time looking through our collection of 145 available holiday cottages and find the perfect one waiting for you. 

We have 145 self catering cottages for 4 on the Isle of Wight

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £439

Spindrift

4437

Tucked away but near the beach in Seaview, Isle of Wight.


This gorgeous two bedroom terraced cottage is a few minutes from the beach, right in the heart of Seaview village, offering an ideal holiday bolthole on the picturesque Isle of Wig...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £439

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £439

Pebbles

4398

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


This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely patio area to the rear and outdoor seating so you can enjoy dining in the Is...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £439

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £441

Fir Cottage

3602

2 bedroom self catering cottage near the beach in St Helens, Isle of Wight.


Located in a quiet lane a few steps from St Helens village green, Fir Cottage is a freshly decorated, refurbished Victorian semi-detached house, complete with all modern amenities....

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £441

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £449

6 St Josephs

3846

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £449

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £456

2 Bagwich Barn

3516

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting with...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £456

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £456

1 Bagwich Barn

3501

2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.


A barn conversion set over two floors, in a rural setting, with a welcoming rustic feel to it. 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight from which...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £456

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £456

2 Bermuda

3517

2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £456

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £459

Spinnakers

3659

2 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.


A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, semi-detached Spinnakers is situated on a small private estate w...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £459

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £464

1 Starboard House

3507

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the centre of Seaview village and enjoys uni...

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £464

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £473

Westhill View

4882

2 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.


With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £473

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Loading more