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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winterbourne Steepleton holiday rentals

A modern living room with a wooden staircase, a flat-screen TV on a wooden stand, a cozy sofa, and a window with a view.

1. Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
3.0 star property
Bridport
The price is 2.362.900 ₫
4.902.910 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

2. 2 Bathsheba Terrace

2 Bathsheba Terrace
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (2 reviews)
"Everything was there that we needed. It was clean, well laid out and comfortable. "
Canada
Rachael
The price is 12.886.977 ₫
15.464.372 ₫ total
includes taxes & fees
30 Oct - 31 Oct
2 Bathsheba Terrace
A stone building with a tiled roof, a wooden bench, and a sign indicating a reception area.

3. Little Norton Mill

Little Norton Mill
4.0 star property
Stoke-sub-Hamdon
10.0 out of 10, Exceptional, (38 reviews)
"A beautiful location. Spotlessly clean and we wanted to stay longer. Thank you for meeting us and making us feel welcome. Carl and Jo"
United Kingdom
Timothy Carl
The price is 3.049.458 ₫
3.659.350 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Little Norton Mill
A modern living room with a sofa, coffee table, and a kitchen area with a washing machine.

4. Streamside Apartments

Streamside Apartments
3.5 star property
Yeovil
10.0 out of 10, Exceptional, (37 reviews)
"Excellent accommodation!"
Norway
Anonymous traveller
The price is 3.790.287 ₫
3.790.287 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Streamside Apartments
A narrow waterway flanked by lush greenery and a traditional building with a tiled roof.

5. The Coach House - Trinity Lodge

The Coach House - Trinity Lodge
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (1 review)
"Klein, aber fein, sehr ruhige Lage alles sehr sauber mit dem Hund ideal Zentral gelegen Umkreis von einer knappen Stunde kann man ne ganze Woche jeden Tag was anderes anschauen der Gastgeber sehr angenehm"
Germany
Steffen
The price is 10.221.716 ₫
12.266.059 ₫ total
includes taxes & fees
30 Oct - 31 Oct
The Coach House - Trinity Lodge
A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

6. The Little Cottage

The Little Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Clean cottage, great location, comfortable beds."
Australia
Lea
The price is 16.694.493 ₫
20.033.392 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Little Cottage
A residential property with a patio, a sliding glass door, and a brick exterior.

7. Cedar Drive

Cedar Drive
2.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"So clean I could roll around in the property, also very thoughtful of the host, even a fly squatter was available. Would highly recommend if you’re in the area."
United Kingdom
David
The price is 14.995.755 ₫
17.994.906 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Cedar Drive
Property grounds

8. Hide-a-way

Hide-a-way
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (2 reviews)
"It was in a peaceful location, although a bit far for walking into town. But the facilities were spot on, though there is no oven to cook proper meals. For someone who needs a quiet, chilled out, restful timeout, it is the perfect place to stay."
United Kingdom
Kim
The price is 11.920.454 ₫
14.304.545 ₫ total
includes taxes & fees
24 Oct - 25 Oct
Hide-a-way
A traditional stone building with a green door, two windows, and a sign reading "The Old School House."

9. The Old School House

The Old School House
3.5 star property
Dorchester
10.0 out of 10, Exceptional, (1 review)
"a spacious and comfortable property that was well equipped for our stay"
United Kingdom
NIGEL
The price is 16.284.453 ₫
19.541.344 ₫ total
includes taxes & fees
30 Oct - 31 Oct
The Old School House
A coastal beach with a prominent rock arch formation, sandy shores, and cliffs.

10. Agua de Plata, 26 Wakeling Island, Silverlake

Agua de Plata, 26 Wakeling Island, Silverlake
3.0 star property
Dorchester
9.0 out of 10, Wonderful, (2 reviews)
"It was amazing Anyone who travels to this part of the country needs to stay here It was beyond our expectation"
United Kingdom
barry
The price is 23.723.753 ₫
28.468.504 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Agua de Plata, 26 Wakeling Island, Silverlake
A traditional stone building with a thatched roof, a small window, and a sign prohibiting parking on the grass.

11. Badgers Cottage

Badgers Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Nice"
United Kingdom
Neil
The price is 14.966.467 ₫
17.959.760 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Badgers Cottage
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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Top Winterbourne Steepleton Hotel Reviews

Sleeping Bear Hotel Dorchester

Sleeping Bear Hotel Dorchester

10/10 Excellent
"Lovely place to stay, convenient for town and for visiting Dorsey County Hospital which was my main reason for visiting Dorchester."
Alan Peter 3-night trip
Posted 11 hours ago
Sleeping Bear Hotel Dorchester

Frequently asked questions

Can I find holiday rentals in Winterbourne Steepleton?

Yes, there are holiday rentals close to the most popular sights in Winterbourne Steepleton, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Winterbourne Steepleton?

While exploring the area, visit family-friendly sights like Abbotsbury Swannery, or get outside and enjoy nature at Dorset and East Devon Coast. Tutankhamun: The Exhibition and Bowleaze Cove Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in Winterbourne Steepleton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winterbourne Steepleton. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for family trips or small group gatherings.