Holiday cottages for September on the Isle of Wight
If Septembers past are anything to go by, this is often one of the loveliest months to enjoy a holiday cottage on the Isle of Wight.
The beaches are still peachy, the sea's had all summer to warm up and the schools have gone back. So you can have more sand, more cliffs and more moor to yourself. Use the search options on the left to choose your holiday dates. We've got 157 holiday cottages on the Isle of Wight available for your September break.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
157 Self Catering Cottages on the Isle of Wight
40 Trelawny Way
35553 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...
Price per week £405 - £641
2 Sea Whispers
39783 bedroom self catering cottage near the beach in Seaview, Isle of Wight
This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...
Price per week £405 - £615
Park Lodge Annexe
37202 bedroom, dog friendly holiday apartment near the beach in Shanklin.
Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...
Price per week £407 - £511
September Cottage
36553 bedroom self catering cottage near the beach in Brook.
September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...
Price per week £413 - £601
Dogs go free on holidays starting between 29th June to 5th July.
Treat your four legged friend to a holiday
Holidays starting between 29th June to 5th July 2018 inclusive will have the cost of the dog(s) removed from their final payment on checkout.
Does not apply to bookings already made.
Chillerton Farm Barn
39643 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight
This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...
Price per week £495 - £695
Westhill
41053 bedroom self catering apartment near the beach in Seaview, Isle of Wight
An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...
Price per week £550 - £775
The Old Boat House
36763 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
The Old Boat House is an attractive period cottage set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This is a charming family home and can be rented...
Price per week £567 - £861
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...
Price per week £612 - £893
Bella Cottage
39033 bedroom self catering cottage in Newport, Isle of Wight
Located in the centre of the Island on the outskirts of the town of Newport, this is perfectly located to explore different places on the Isle of Wight. In the colder months, wrap ...
Price per week £760 - £860
3 Astra House
35413 Astra House is a comfortable first floor apartment within a converted Victorian House
3 Astra House is a comfortable first floor apartment within a converted, red brick Victorian house, located on a quiet residential no-through road in Seaview. Offering light and sp...
Price per week £334 - £525
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.