Luxury Cottages in May on the Isle of Wight

Put a spring in your step and stay in a luxury self-catering cottage on the Isle of Wight this May. Whether it's a May half-term holiday, a short break over a May bank holiday or a much-anticipated getaway ahead of the summer crowds, our portfolio of 87 available properties provide an idyllic base. Look forward to adventure, fun and total comfort all with the Isle of Wight's stunning backdrop. Read more

Whoever you want to spend your dream holiday with on the Isle of Wight, be it a solo retreat, family holiday or catch up with friends, the choice is yours. One thing is for certain though: where you want to spend it. At Classic Cottages, we offer the finest quality self-catering accommodation around. With each property carefully selected onto our books, we personally inspect all of our cottages to maintain the highest standards. 

From cosy one-bed retreats to spacious family-friendly properties, we have a wide range of properties ready and waiting to welcome you. Fall in love with a beach-side cottage with spectacular sea views, or luxuriate in a rural retreat with a beautiful garden perfect for long afternoons in the sunshine. Pick a private escape set back away from it all, or choose a bolthole close to all the local amenities. The holiday of your dreams awaits.

May Cottages on the Isle of Wight 

At Classic Cottages, we understand the importance of accommodation in making or breaking your holiday. That's why all of our self-catering cottages have been handpicked; personally inspected to make sure only the best make it onto our books. You needn't worry about cramming everything into your luggage either. Each of our cottages is equipped with a full inventory. Everything from your bed linens to your morning coffee pot to enough crockery is provided, so you needn't worry about a thing. 

See our range of 87 available cottages in May on the Isle of Wight

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £340

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £340

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £550

19 Seaview Bay

4926

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island Coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel,...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £550

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

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £550

18 Seaview Bay

4996

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming apartment found in a small development close to the village centre...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £550

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £639

Oceanix

4900

1 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.


A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect sea-side getaway for your next Isle of Wight holiday. The property has been thoug...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £639

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £639

Buckland Cabin

4853

1 bedroom cabin near the beach in Seaview, Isle of Wight.


Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £639

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £445

Cockleshells

3815

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The accommodation offers a double...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £445

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £480

The Beach Retreat

3665

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


This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £480

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

Dairy Cottage

3912

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

Orchard Cottage

3936

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £502

Faithfull Cottage

3600

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £502

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