Isle of Wight Cottages Sleeping 2

Whether you’re looking for a romantic break or a chance to rest and recharge with a family member, there’s a cottage that sleeps two for every visit on the Isle of Wight.

Staying in a cottage for two gives you enough space to relax and unwind without being too big. Plan a getaway to the island and enjoy the broad diversity that it has to offer. Plan a romantic break together for a special occasion or take a trip with a family member for some quality time together. 

As soon as you cross the Solent, you’ll feel all your worries melt away. This is where your holiday begins. Spend the journey nestled together discussing your plans and what you’d like to see the most before heading back to your car to drive on to the isle.

For walkers, the hills of West Wight make an excellent playground for two. Mix the coast paths with walks further inland around Freshwater Bay or Brighstone to really see the nature of the island. If you prefer a classic promenade with golden sands, waltz along the coast at Sandown, Shanklin and Ventnor. These classic Victorian holiday locations still have their historic charm. Shanklin Old Town is particularly picturesque with thatched roofs and souvenir shops. There’s also amazing opportunities for cycling: there are several cycling festivals throughout the year and plenty of routes for all abilities across the island.

Finding foodie hotspots isn’t hard here. Newport plays host to some excellent restaurants. Thompson’s offers a classic dining experience with an amazing display of culinary expertise. For taste with a twist, we love Nomad. A cool restaurant with a focus on Mexican and Asian fusion. They bring your food out on tiles and have a set menu called ‘Shut and feed me’. What more is there to love? For daytime dining, Ventnor and Godshill in the South have a host of individual cafes to pop in for a cup of tea whilst exploring the island. Whilst in Ventnor, stop by the beautiful botanical gardens to take some lovely photographs with your travel buddy and enjoy the tranquillity of this part of the isle.

No matter the time of year, a lovely cottage for two will make a beautiful bolthole for couples, a homely hub for friends and the perfect base for family visiting the island together.

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

We have 196 self catering cottages on the Isle of Wight that sleep two.

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £483 - £1090

3 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight


Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £495 - £1100

We’re here to help you find your perfect place to stay 7 days a week.

3 bedroom self catering cottage in East Cowes, Isle of Wight


Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £495 - £995

3 bedroom self catering cottage with sea views in St Helens, Isle of Wight


With wonderful views over Bembridge Harbour and Brading Marshes, 5 Yar Quay is a charming three storey house in St Helens within walking distance of Bembridge Village. The sitting-...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £495 - £1150

View
  • 10% off

    27 Apr 2018 - 4 May 2018

    £619.97 £558.00

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


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £495 - £1100

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


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £504 - £1170

3 bedroom self catering apartment near the beach in Seaview.


Perched right on the waterfront opposite Seaview beach, 3 Quay Rocks has unrivalled views of the attractive seafront and beyond, out to the ships passing by on the Solent. The apar...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £510 - £1065

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


Tucked away down a quiet side street in the idyllic village of Seaview, Portholes is a fantastic holiday home just minutes away from the sea. All within walking distance from your ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £520 - £1200

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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


Rose Villa is a little gem of a home in Yarmouth with its open plan kitchen and dining-table close to the doors to the garden, capturing the light nicely on a sunny day. Continuing...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £520 - £1160

3 bedroom, dog friendly cottage near the beach in East Cowes, Isle of Wight.


This truly lovely holiday home, with a wood-burner, is a great choice whatever the season. 1 Barton Lodge is a beautiful property which has been lovingly restored with your comfort...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £544 - £1190

Loading more