Isle of Wight Cottages Sleeping 2

Whether you’re looking for a romantic break in a cosy cottage 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. With each property handpicked and carefully inspected, we pride ourselves on offering the finest quality self-catering accommodation with excellent customer service. Book with confidence with Classic Cottages. 

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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

177 self-catering cottages on the Isle of Wight that sleep 2

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

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


This completely refurbished cottage is nestled at the end of Ryde Road, just a short walk from the beach and Seaview village. With off-street parking and a lovely large garden to t...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

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

7 nights from £850

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


A wonderful contemporary beach house, offering accommodation for eight, within a few minutes walk to the beach and Bembridge village. There is a spacious kitchen/diner with doors o...

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

7 nights from £850

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

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

7 nights from £852

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


Walnut Cottage is a real find if you're looking for a spot of luxury on holiday. Tucked away in central Seaview village Walnut offers spacious accommodation over two floors and an ...

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

7 nights from £852

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £867

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


Tides Reach is a wonderful, newly modernised family house along the Seaview Duver just a short walk into Seaview Village and the Yacht Club. Tides Reach has a stylish open plan sit...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £867

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

7 nights from £1000

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

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

7 nights from £1000

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1200

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1200

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1250

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


This absolutely stunning barn conversion is a little slice of luxury just outside the village of St Helens, only a short stroll to the St Helens Duver, sand dunes, beach and the Ba...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1250

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1375

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


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £1375

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £660

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


6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £660

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £718

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


Middle Lodge is a beautiful 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the near-east side of the Island. It would be ideal f...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £718

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