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Winterbourne Steepleton Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winterbourne Steepleton holiday rentals

A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

1. 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 S$746
includes taxes & fees
20 Oct - 21 Oct
2 Bathsheba Terrace
Room

2. Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
3.0 star property
Bridport
The price is S$241
includes taxes & fees
9 Nov - 10 Nov
Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
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 S$200
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 S$186
includes taxes & fees
17 Oct - 18 Oct
Streamside Apartments
A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

5. 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 S$986
includes taxes & fees
27 Oct - 28 Oct
The Little Cottage
A wooden deck with a pergola, a table with chairs, and a brick pathway.

6. Home Waters

Home Waters
3.5 star property
Wyke Regis
10.0 out of 10, Exceptional, (1 review)
The price is S$1,052
includes taxes & fees
31 Oct - 1 Nov
Home Waters
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
Cedar Drive
A traditional stone building with a thatched roof, a small window, and a sign prohibiting parking on the grass.

8. Badgers Cottage

Badgers Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Nice"
United Kingdom
Neil
The price is S$884
includes taxes & fees
21 Oct - 22 Oct
Badgers Cottage
A narrow waterway flanked by lush greenery and a traditional building with a tiled roof.

9. 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 S$604
includes taxes & fees
30 Oct - 31 Oct
The Coach House - Trinity Lodge
Property grounds

10. 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 S$702
includes taxes & fees
27 Oct - 28 Oct
Hide-a-way
A traditional stone building with a green door, two windows, and a sign reading "The Old School House."

11. 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 S$962
includes taxes & fees
18 Oct - 19 Oct
The Old School House
A rustic kitchen with wooden beams, a stone wall, a sink, a stove, and a washing machine.

12. Way's Forge

Way's Forge
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Way's Forge is a quirky, convenient accommodation for exploring a wide variety of locations in the area and further afield. . It was a very comfortable stay and we enjoyed it very much. "
United Kingdom
Virginia
The price is S$879
includes taxes & fees
11 Nov - 12 Nov
Way's Forge
A coastal area with a beach, boats, and a clear sky.

13. Marina Vista

Marina Vista
3.5 star property
Southlands
10.0 out of 10, Exceptional, (2 reviews)
"Great, well appointed apartment which is very central. Can be quite noisy at night especially having to have the windows open when it’s hot. Seemed to be a popular location for late night drinkers to have heart to hearts in the wee hours. Can’t fault the apartment, it had everything you could need. Minutes away from the town and beach. On the rainy days we had there were even board games for kids which my son loved. Thanks for a great stay. "
United Kingdom
M
Marina Vista
A coastal beach with a prominent rock arch formation, sandy shores, and cliffs.

14. 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 S$1,401
includes taxes & fees
19 Oct - 20 Oct
Agua de Plata, 26 Wakeling Island, Silverlake
A grassy area with a view of a calm body of water and distant landforms.

15. Lobster Cottage

Lobster Cottage
3.5 star property
Rodwell
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and included everything you would need. The outside space was disappointing as it was just a table and chairs in a small concrete space rather than what is shown on the pictures depicting the outside space. The location made ot easy to score with a few shops, pubs and places near by."
United Kingdom
Sharon
The price is S$860
includes taxes & fees
18 Oct - 19 Oct
Lobster Cottage
A modern kitchen with a dining area, featuring a large window, a microwave, and a sink.

16. Coastguard Lookout

Coastguard Lookout
2.0 star property
Wyke Regis
The price is S$775
includes taxes & fees
18 Oct - 19 Oct
Coastguard Lookout
A bedroom with a green upholstered headboard, a floral bedspread, and a painting of flowers on the wall.

17. Rodwell Holt

Rodwell Holt
2.0 star property
Weymouth
The price is S$759
includes taxes & fees
27 Oct - 28 Oct
Rodwell Holt
A harbor with boats docked, wooden piers, and a row of buildings in the background.

18. 2 Driftwood

2 Driftwood
3.5 star property
Bridport
10.0 out of 10, Exceptional, (2 reviews)
"Our family had a wonderful time at West Bay staying at 2 Driftwood. The accommodation was clean, warm and situated in the heart of the town. It was only a few minutes walk from the beach, restaurants and the jetty. It is such a pretty place, the view along the beach is stunning and everyone we met was friendly and welcoming. I recommend staying here."
United Kingdom
Louis
The price is S$862
includes taxes & fees
23 Oct - 24 Oct
2 Driftwood
A coastal view with boats on the water, a sandy beach, and a clear sky.

19. Beach View House

Beach View House
3.5 star property
Wyke Regis
10.0 out of 10, Exceptional, (1 review)
"Vi var meget godt fornøyde med både beliggenhet og renhold, og hadde veldig fine dager her. Dette kan vi anbefale på det varmeste!"
Norway
Arve Moen
The price is S$1,241
includes taxes & fees
21 Oct - 22 Oct
Beach View House
A room with a large window overlooking a body of water, a small table with candles, and a mirror on the wall.

20. Still Waters

Still Waters
2.0 star property
Wyke Regis
10.0 out of 10, Exceptional, (1 review)
"Amazing property, had the best week staying there. Location, facilities, space.. everything!! Will be back"
United Kingdom
Rory
The price is S$1,362
includes taxes & fees
27 Oct - 28 Oct
Still Waters
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

The Manor Hotel by Greene King Inns

The Manor Hotel by Greene King Inns

8/10 Good
"Great for a quick one night stop. Staff all friendly"
Daniel 1-night trip
Posted 1 day ago
The Manor Hotel by Greene King Inns

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.