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. 

 

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

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

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


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

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

Price per week £580 - £1474

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


A classic red brick Victorian home, with lovely bay windows adding to the period charm, Haslemere is a family home just a short walk from Yarmouth village. The property has an invi...

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

Price per week £588 - £1010

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

3 bedroom, rural self catering cottage in Newport, Isle of Wight


This property is a truly idyllic cottage situated in the grounds of a farm, with stunning countryside views and a lovely garden. This is what you would describe as holiday heaven. ...

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

Price per week £600 - £1300

3 bedroom, rural self catering cottage with estuary views near Newport, Isle of Wight


This stylish three-storey town house is located in the exclusive development of Island Harbour, with two balconies overlooking the busy marina and providing the perfect sun-trap to...

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

Price per week £600 - £1400

3 bedroom self catering cottage near the beach in Seaview.


In a quiet position within a secluded courtyard in Seaview, Raleigh Cottage is complete with a cosy wood-burning stove for the cooler months, lovely decking for outside dining and ...

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

Price per week £625 - £1400

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

Price per week £630 - £1428

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 Fri

Price per week £650 - £1530

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

Price per week £700 - £1400

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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


A gorgeous Victorian three bedroom house on the outskirts of Shanklin with a lovely secluded garden and a private swimming pool. Beautifully decorated throughout, the Owner has tak...

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

Price per week £706 - £1595

3 bedroom cottage with hot tub and 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

Price per week £795 - £1500

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