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 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

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


The Limes is nestled in a corner of St Helens Green overlooking the cricket pitch, with far reaching views from the rear master bedroom over Brading Marshes. The location is peacef...

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

Price per week £426 - £980

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

3 bedroom self catering cottage near the beach in Shanklin.


25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...

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

Price per week £427 - £939

3 bedroom self catering apartment near the beach in Seaview.


Pandora Lodge is a lovely ground floor apartment forming part of a larger Victorian property in central Seaview. With sea views from the sitting-room and large bay windows featured...

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

Price per week £429 - £969

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


Nestled in the heart of Seaview village this lovely ground floor apartment is a stone’s throw from the sea front and all the village amenities. Seaview is an idyllic Edwardian reso...

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

Price per week £435 - £1020

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


Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...

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

Price per week £436 - £969

View
  • 10% off

    20 Oct 2018 - 27 Oct 2018

    £620.92 £558.83

3 bedroom self catering cottage in East Cowes, Isle of Wight


Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...

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

Price per week £440 - £1015

View
  • 20% off

    20 Oct 2018 - 27 Oct 2018

    £639.98 £511.99

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


East Gull Sands is an attached, comfortably furnished, beachfront holiday home in Seaview. Sitting right opposite the beach this property has sea views from the upstairs double bed...

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

Price per week £451 - £1010

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

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


A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...

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

Price per week £453 - £1082

View
  • 10% off

    19 Oct 2018 - 26 Oct 2018

    £650.31 £585.28

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


Where to start in describing this picture-perfect property in Ventnor? Originally built in 1868 and part of Ventnor Botanic Gardens the cottage now affords all modern conveniences ...

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

Price per week £453 - £1140

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