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Winterbourne Steepleton Vacation Rentals

Check prices for these dates

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

Our top choices for Winterbourne Steepleton vacation 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
$484 nightly
The price is $581
Oct 20 - Oct 21
Total with taxes and fees
2 Bathsheba Terrace
A dining table with pink plates, a glass, and a spoon set. There is a window with white curtains and a view of a building outside.

2. Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
3.0 star property
Bridport
$157 nightly
The price is $188
Nov 4 - Nov 5
Total with taxes and fees
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
$130 nightly
The price is $156
Nov 2 - Nov 3
Total with taxes and fees
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 traveler
$133 nightly
The price is $133
Nov 12 - Nov 13
Total with taxes and fees
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
$640 nightly
The price is $768
Oct 27 - Oct 28
Total with taxes and fees
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)
$682 nightly
The price is $819
Oct 31 - Nov 1
Total with taxes and fees
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
$575 nightly
The price is $690
Nov 6 - Nov 7
Total with taxes and fees
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
$574 nightly
The price is $688
Oct 21 - Oct 22
Total with taxes and fees
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
$392 nightly
The price is $470
Oct 30 - Oct 31
Total with taxes and fees
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
$457 nightly
The price is $548
Oct 19 - Oct 20
Total with taxes and fees
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
$624 nightly
The price is $749
Oct 19 - Oct 20
Total with taxes and fees
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
$570 nightly
The price is $684
Nov 11 - Nov 12
Total with taxes and fees
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
$909 nightly
The price is $1,091
Oct 19 - Oct 20
Total with taxes and fees
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
$558 nightly
The price is $669
Oct 19 - Oct 20
Total with taxes and fees
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
$503 nightly
The price is $603
Oct 26 - Oct 27
Total with taxes and fees
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
$494 nightly
The price is $593
Oct 23 - Oct 24
Total with taxes and fees
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
$559 nightly
The price is $671
Oct 23 - Oct 24
Total with taxes and fees
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
$805 nightly
The price is $966
Oct 21 - Oct 22
Total with taxes and fees
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
$883 nightly
The price is $1,060
Oct 27 - Oct 28
Total with taxes and fees
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

Fairhaven Hotel

Fairhaven Hotel

8/10 Good
"It was a last minute booking . Good value for the money. Breakfast was excellent freshly cooked. very attentive staff. Had the pizza in the evening beautifully cooked very fresh. Ideal hotel if you want to be close to the town. Has lift so easy for people who struggle with mobility issues."
Angela 2-night trip
Posted 6 hours ago
Fairhaven Hotel

Find out more about Winterbourne Steepleton

Everything you need to know about Winterbourne Steepleton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winterbourne Steepleton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winterbourne Steepleton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winterbourne Steepleton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterbourne Steepleton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winterbourne Steepleton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $156 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winterbourne Steepleton rentals

At Expedia, we put the best Winterbourne Steepleton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winterbourne Steepleton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winterbourne Steepleton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterbourne Steepleton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Winterbourne Steepleton?

Yes, we give you a choice of vacation rentals close to well known local attractions in Winterbourne Steepleton, or you can select a more secluded option if you're looking for relaxation.

What's the top vacation rental that Winterbourne Steepleton has to offer?

Holiday Home of the Year | Sleeps 20 | Tennis, Gardens | 1m Jurassic Coast Beach: This vacation home rental outside of Winterbourne Steepleton is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 larger area.

What’s a vacation rental in Winterbourne Steepleton like?

Vacation rentals are private properties you can stay in for a long or short time in Winterbourne Steepleton. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.