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 206 self catering cottages on the Isle of Wight that sleep two.

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


Flackstead is a unique eco-friendly house which has breath-taking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of conte...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1650 - £2950

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


Ashmead Cottage has been thoughtfully decorated throughout offering three lovely bedrooms and two modern bathrooms. The kitchen opens out onto a charming private decked-area with o...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £437 - £990

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

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £499 - £1325

3 bedroom, dog friendly cottage near the beach near Old Freshwater, Isle of Wight.


If you're after a period property that is full of character, then Afton Thatch is the place for you. With its thatched roof, oak beams, open fireplaces and glorious river views, th...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £655 - £1535

4 bedroom, rural self catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location, surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £670 - £1556

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


Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £781 - £1990

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


Large and modern, Skylark Cottage is one of the premium properties available at Salterns Village, an exclusive small gated development on the edge of Seaview. The village has a lov...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £479 - £1499

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


One of a handful of pretty pastel beach bungalows located in Salterns Village, Curlew Cottage is a small, exclusive development at the edge of Seaview that offers securew communal ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £479 - £1499

Our property managers are local experts who handpick perfect places to stay.

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


Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation. This detached property has a ground floo...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £500 - £1153

4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £532 - £1208

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