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 188 available self-catering cottages and take a step closer to the holiday of a lifetime.

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 188 available holiday cottages and find the perfect one waiting for you. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 188 self catering cottages for 4 on the Isle of Wight

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview, and just a short walk from the beach and shops. Delightfully renovated, this co...

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

Price per week £347 - £730

2 bedroom self catering apartment with sea views in Seaview.


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

Price per week £348 - £735

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


Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...

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

Price per week £350 - £867

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


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

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

Price per week £350 - £867

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


Quiet Corner is a modestly furnished, comfortable cottage situated in the popular village of Bembridge, less than a mile from Bembridge beach. As its name suggests it's tucked away...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

Price per week £351 - £790

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


Number 9 has an open plan living-room with wood-burning stove for cosy nights in and door opening out to a decked area for the warmer nights. There is seating on the decking to rel...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £351 - £730

Dogs go free on holidays starting between 29th June to 5th July.

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


Number 17 is located at the end of the development looking out to the shared communal grounds and Seaview Nature Reserve. There is a downstairs twin bedroom with a walk-in shower a...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £351 - £730

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


Number 18 is a two bedroomed chalet on the small Tollgate holiday complex on the Seaview Duver. These are ideal to rent out for larger families as you can rent next door and other ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £351 - £730

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


23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £351 - £730

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


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

Price per week £352 - £780

Loading more