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 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £643

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

7 nights from £643

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £663

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


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £663

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

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

7 nights from £700

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


With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...

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

7 nights from £700

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

7 nights from £925

3 bedroom self catering houseboat with sea views in Bembridge, Isle of Wight


Welcome aboard this luxury two-storey houseboat in Bembridge harbour with two rear balconies and a private pontoon, you can kayak right up to your back door just in time for lunch....

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

7 nights from £925

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

7 nights from £954

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


This absolutely stunning property is laid over five mezzanine floors, has two sea-facing balconies and a hot tub with a sea view! Beautifully decorated throughout, The Lodge offers...

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

7 nights from £954

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1683

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

7 nights from £1683

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

7 nights from £445

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


If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...

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

7 nights from £445

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

7 nights from £546

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

7 nights from £546

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

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

7 nights from £684

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

7 nights from £684

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

7 nights from £700

3 bedroom self catering apartment with sea views in Seagrove Bay, Isle of Wight


In the most spectacular location just a few metres from Seagrove Bay, this two-storey apartment is in a prime holiday location with a large decked balcony to admire the stunning se...

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

7 nights from £700

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