Popular property types See all properties

24/7 “On Holiday” Support

Our friendly UK team are here to help, in case of any emergency.

Award Winning Holiday Experts

Over 30 years of experience in UK self-catering holidays.

B Corp Certified Business

Committed to making a positive social and environmental impact.

Safe & Secure Payments

Flexible payment options for peace of mind.

Isle of Wight Cottage Holidays

REFINE SEARCH

Your Isle of Wight & Hampshire search returned 314 cottages

Most relevant
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Primrose Cottage is a delightful, detached home resting in St. Helens, on the Isle of Wight. Close to a shop and a pub. Close to a beach. Near AONB. Sandown 4.3 miles; Ryde 4.5 miles; Newport 10.6 miles. (Ref. 1151022)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £496

  • Sleeps10
  • Bedrooms5
  • PetsYes
  • Sykes rating

Appuldurcombe Farmhouse is a historic, detached property in Wroxall, near Ventnor, Isle of Wight. Grade-II listed property. Woodburning stove. Pet-friendly. Ventnor 3.1 miles; Godshill 3.3 miles; Shanklin 4.2 miles. (Ref. 1070757)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £1127

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3

    Good

  • Sykes rating

This stylish workshop conversion resides in Ventnor, Isle of Wight. Smart TVs. Close to amenities and beach. En-suite bathrooms. Summer house. Newport 11.1 miles; Cowes 15.5 miles. (Ref. 1115193)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £608

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A delightful, single-storey, detached timber-clad cottage in the village of Boldre in the New Forest National Park. Well-presented, furnished to a good standard. Woodburner. Lymington 2.6 miles. (Ref. 25473)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from £360

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Garstons Barn is a lovely, three-bedroom barn conversion resting in Gatcombe near Newport, Isle Of Wight. In an AONB. Countryside views. Open-plan. Off-road parking. Cowes 9.5 miles; Ryde 10.9 miles; Yarmouth 12.3 miles. (Ref. 1133914)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £628

Last booked yesterday
See more details
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stable conversion cottage set in beautiful countryside, but only 2 miles from the Victorian seaside resort of Ryde. Many interesting shops and restaurants and sandy beach close by. Sandown 7 miles. (Ref. 10062)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly

7 nights from £335

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

This stunning, ground-floor holiday home rests on the outskirts of Fareham, Hampshire. Smart TV. Woodburning stove. Close to amenities. Bedrooms with en-suites. Portchester 6.7 miles; Southampton 10.1 miles; Portsmouth 12.2 miles. (Ref. 1111930)

  • Wi-fi
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £737

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A delightful semi-detached cottage perched in the seaside resort of Shanklin in the Isle of Wight. Off-road parking. Pet friendly. WiFi. Godshill 4 miles; Sandown 4.1 miles. (Ref. 1068112)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Sky TV

7 nights from £450

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.0

    Good

  • Sykes rating

A remarkable three-bedroom holiday home resting in Sandown, on the Isle of Wight. Open-plan. Family-friendly. Close to the beach. Ryde 6.5 miles; Cowes 14 miles; Yarmouth 18.9 miles. (Ref. 1073331)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £514

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A beautiful three-bedroom apartment set in a converted church in Ventor, Isle of Wight. Smart TV. Original features. Near a beach. In AONB. Newport 12.1 miles; Cowes 15.9 miles. (Ref. 1072796)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £588

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Beautifully located barn conversion cottage in the small hamlet of Gatcombe. Well-equipped, comfortable accommodation. Private patio with furniture. Stunning walks and mountain biking from cottage. Newport 4 miles. (Ref. 913107)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £436

Last booked yesterday
See more details
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Northern Byre is a delightful, four-bedroom barn conversion resting in Sopley, Hampshire. Pet-friendly. Contemporary. Close to amenities and attractions. Christchurch 3 miles; Ringwood 6.3 miles; Bournemouth 7.5 miles. (Ref. 1141030)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Washing machine
  • Sky TV

7 nights from £823

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

Flexford Mill Cottage, a stunning holiday home in Sway near the market town of Lymington, Hampshire. Pet-friendly. Within New Forest National Park. Lyndhurst 7.8 miles; Christchurch 11.8 miles; Southampton 17.7 miles. (Ref. 1142485)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £1060

Last booked yesterday
See more details
  • Sleeps2
  • Bedrooms1
  • PetsYes
  • Sykes rating

2 Welford Barns, a delightful barn conversion rests in Fordingbridge, Hampshire. Close to amenities. Off-road parking. Outdoor space with furniture. Salisbury 11.3 miles; Bournemouth 16.6 miles; Cranborne Chase National Landscape 18.9 miles. (Ref. 1162549)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom

7 nights from £399

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A marvellous townhouse sitting on the coast in Portsmouth, Hampshire,sea views. Near the beach. Close to amenities. Hayling Island 9.9 miles; Southampton 21.3 miles; New Forest 34.3 miles. (Ref. 1070068)

  • Wi-fi
  • Dishwasher
  • Baby-friendly

7 nights from £1614

Last booked 2 days ago
See more details
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A wonderful property with a lot of character, St. Michael’s House is the perfect property for families or a group of friends. Dog-friendly. Near the coast. Bembridge 2.3 miles. (Ref. 1000597)

  • Wi-fi
  • Washing machine

7 nights from £439

  • Sleeps11
  • Bedrooms5
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Spacious, character barn conversion 1.5 miles from the Hampshire village of West Tytherley. Exposed wooden beams. En-suite. Dog-friendly. Countryside views. (Ref. 983306)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £1285

Last booked 3 hours ago
See more details
  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

The Anchorage is a pleasant terraced house in the village of Bembridge on the Isle of Wight. Pet-friendly. Open-plan. Off-road parking. Child-friendly. Ryde 7.3 miles; Newport 11.3 miles; Cowes 15.8 miles; Yarmouth 20.7 miles. (Ref. 1153862)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly

7 nights from £559

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This charming three-bedroom holiday home rests in Havant, Hampshire. Pet-friendly. Enclosed garden. Off-road parking. Waterlooville 4.8 miles; Portsmouth 8.6 miles; Chichester 9.9 miles. (Ref. 1121678)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £434

Last booked 2 days ago
See more details
  • Sleeps12
  • Bedrooms6
  • PetsYes
  • Sykes rating

The Old Dairy is a detached barn conversion resting in Wroxall, near Ventnor, Isle of Wight. Near AONB. Countryside views. Woodburning stove. Pet-friendly. Ventnor 3.1 miles; Godshill 3.3 miles; Shanklin 4.2 miles. (Ref. 1070762)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £1340

Last booked 2 days ago
See more details

If you're looking for an alternative holiday, then a cottage on the Isle of Wight may just be right for you. Located just three miles off the Hampshire coast, the Isle of Wight's easy-going pace of life feels a world away from the bustle of the mainland.

Why Isle of Wight Holidays?

The Isle of Wight's gloriously sunny climate helps make it one of the UK's most desirable holiday locations. During a summer Isle of Wight holiday, head to one of many fun-filled festivals, or simply admire the ever-present scenery on foot or bike. The coastline is just as impressive as the countryside, with soft sandy beaches around every corner. The Isle of Wight is a marvellous holiday spot all year round, with much to explore, even when the weather isn't so good. Our Isle of Wight Travel Guide tells you all you need to know about Isle of Wight holidays.

Places to Visit During Isle of Wight Holidays

This scenic island is a mere 25 miles wide, making the entire place accessible by car. Despite its size, there is a fabulous variety of things to see and do to suit tastes of all kinds. The west of the island hosts both the Isle of Wight AONB and the Hamstead Heritage Coast, showcasing jaw-dropping scenery for lovers of the outdoors. If you love a bit of history, visit the palatial Osborne House close to Cowes, or admire the striking Carisbrooke Castle near Newport.

When enjoying Isle of Wight holidays, consider visiting places such as:

Bembridge

Freshwater

Ryde

Ventnor

Yarmouth

Types of Isle of Wight Holidays

You can experience the stunning countryside of the island during a glamping break on the Isle of Wight or with a holiday park on the Isle of Wight. Be sure not to leave your canine companion behind by booking a dog-friendly cottage on the Isle of Wight and allow the entire family to enjoy this wondrous location. Why not treat yourself to a touch of class? Choose a luxury Isle of Wight cottage that will provide you with that little something extra. Planning to treat your loved one to a charming weekend away? This array of Isle of Wight short breaks is a great choice. Alternatively, secure a late deal by booking a last-minute Isle of Wight holiday.