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

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

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


24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £847

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £847

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


6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £847

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


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £375 - £847

2 bedroom, dog friendly holiday cottage near the beach in Shanklin, Isle of Wight


This modern and bright bungalow with a sunny garden is perfect for a family holiday and as it has a fully-enclosed rear garden, why not bring your four-legged friends? Sleeping six...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £384 - £850

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


1 Astra House is a comfortable, light and bright ground floor apartment set within a charming Victorian property in Seaview. A small family or several couples travelling together w...

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

Price per week £398 - £895

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

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


30 Seaview Bay is a lovely three-bedroom apartment set over two levels that would suit families or couples. This leafy seafront location is popular and it's easy to see why. Th...

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

Price per week £399 - £878

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


Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family in need an easy, convenient holiday exper...

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

Price per week £410 - £995

3 bedroom self catering cottage near the beach in Seaview.


This modern, well-presented town house is located in a small development in the centre of Seaview. A true home-from-home, 2 Sandpipers is perfect for a coastal break with the famil...

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

Price per week £418 - £965

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


1 Harbour Strand is a town house with jaunty decor, attractive furnishings and interesting prints, including some of the owners own artwork. It offers a games-room, with table-tenn...

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

Price per week £424 - £1245

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