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

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

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


Barton Manor Farmhouse is a beautifully refurbished, 150 year old property set in the delightful grounds of the Barton Estate, adjacent to English Heritage's Osborne House, former ...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1277 - £3120

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £717 - £1928

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £738 - £1683

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


Swift Cottage is a gorgeous, comfortable Edwardian end-of-terrace property, spread over three levels with wooden flooring throughout the kitchen and dining area. The spacious dinin...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £828 - £2045

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


Mariners is a beautiful beachfront property offering light, spacious, contemporary family accommodation. Tastefully refurbished in recent years, this modern property is spread acro...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £873 - £2122

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


Mountbatten Garden Apartment is a fabulous apartment stylishly furnished with four en suite bedrooms and comes with a private courtyard including a six person hot tub. Vibrantly de...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £895 - £2250

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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


Seacrest House is a stunning holiday home with fabulous Solent views across beautiful Appley beach and is perfect for a large family or group of friends looking for a property with...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £989 - £2311

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


This stunning converted coach house, benefitting from a fabulous location within the grounds of the Priory Estate, is an exceptional holiday home-from-home. The Priory Coach House ...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1129 - £2760

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


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is roomy, with plenty of space for the family to spread out. As w...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £1244 - £2642

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


A truly amazing, contemporary home with views directly out to sea, in the popular sailing town of Cowes. Offering exceptional quality throughout the whole home this is a superb bas...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1578 - £2885

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