Photo by Adrian Farwell

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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Tiptoe chalets

A hot tub in a garden with a pergola overhead, surrounded by various plants and a picnic table.

1. Dassia

Dassia
Porchfield
9.6 out of 10, Exceptional, (4 reviews)
"We stayed here over Christmas and it was perfect. Our dog loved the enclosed garden. The kitchen has everything to cook a festive dinner in. We had the log burner on for the day which was great. Would definitely stay again."
United States
Emma
The price is NZ$1,896
includes taxes & fees
12 Nov - 13 Nov
Dassia
A balcony with a view of the sea and parked cars.

2. Princes Esplanade

Princes Esplanade
Gurnard
10.0 out of 10, Exceptional, (4 reviews)
"We loved the beautiful location"
United States
Susan
The price is NZ$1,895
includes taxes & fees
16 Nov - 17 Nov
Princes Esplanade
A row of terraced houses with white and brown brick facades, numbered addresses, and a green door on the right.

3. York Street

York Street
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"It was absolutely perfect ! The house was so well looked after ."
United States
Anonymous traveller
The price is NZ$2,399
includes taxes & fees
10 Dec - 11 Dec
York Street
A rooftop terrace with a table set for dining, overlooking a body of water and a distant shoreline.

4. Penderic, Isle of Wight

Penderic, Isle of Wight
Cowes
The price is NZ$1,647
includes taxes & fees
12 Dec - 13 Dec
Penderic, Isle of Wight
A swimming pool with a stone border, a covered seating area with blue chairs, and a view of the countryside.

5. Rookley Farm Lodge

Rookley Farm Lodge
Rookley
10.0 out of 10, Exceptional, (11 reviews)
"Loved the location, so peaceful and relaxing and private. Loved hearing the lambs in the field, loved the pool. House has everything you could possibly need."
United States
Sue
The price is NZ$3,621
includes taxes & fees
12 Nov - 13 Nov
Rookley Farm Lodge
A balcony with a view of a marina, a grassy area, and a wicker chair with a cushion.

6. Creek View, Isle of Wight

Creek View, Isle of Wight
Wootton Bridge
10.0 out of 10, Exceptional, (4 reviews)
"A truly amazing stay at a wonderful location. A superb home to base an island adventure! VRBO"
United States
Benjamin Gully
The price is NZ$3,531
includes taxes & fees
12 Nov - 13 Nov
Creek View, Isle of Wight
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Tiptoe

Venture to Southampton Cruise Terminal and New Forest National Park—just a couple of the popular sights around Tiptoe.

See all hotels in Tiptoe
A gravel path through a lush green landscape with dense vegetation on either side.
Photo by Adrian Farwell
Open Photo by Adrian Farwell

Top reviews in Tiptoe

An outdoor patio area with wooden pergola, tables, and chairs.
The Bear of Burton

The Bear of Burton

The Bear of Burton
Christchurch

10/10 Excellent

Just brilliant! Lovely staff and lovely room. Breakfast was delicious too
Australia
SUNG
Reviewed February 28, 2026
The Bear of Burton

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