Winterbourne Steepleton Holiday Rentals from NZ$398: Search Short-Term Rentals

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Our top choices for Winterbourne Steepleton holiday rentals

A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

1. The Little Cottage

Weymouth

Lea

includes taxes & fees

26 Sept - 27 Sept

A modern living room with a sofa, coffee table, and a kitchen area with a washing machine.

2. Streamside Apartments

Yeovil

Anonymous traveller

includes taxes & fees

10 Sept - 11 Sept

3. Yeovil 1-bed Annex Sleeps 2 With Wifi

Yeovil

Leigh

includes taxes & fees

1 Sept - 2 Sept

A traditional stone building with a thatched roof and a chimney.

4. Badgers Cottage

Weymouth

Neil

includes taxes & fees

3 Sept - 4 Sept

A narrow waterway flanked by lush greenery and a traditional building with a tiled roof.

5. The Coach House - Trinity Lodge

Dorchester

Steffen

includes taxes & fees

26 Sept - 27 Sept

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

6. 2 Bathsheba Terrace

Dorchester

Rachael

includes taxes & fees

23 Sept - 24 Sept

A rustic kitchen with wooden beams, a stone wall, and a built-in oven.

7. Way's Forge

Dorchester

Virginia

includes taxes & fees

11 Sept - 12 Sept

A traditional stone building with a green door, two windows, and a sign reading "The Old School House."

8. The Old School House

Dorchester

NIGEL

includes taxes & fees

16 Sept - 17 Sept

A coastal view with boats on the water, a sandy beach, and a clear sky.

9. Beach View House

Wyke Regis

Arve Moen

includes taxes & fees

11 Sept - 12 Sept

A coastal area with a beach, boats, and a clear sky.

10. Marina Vista

Southlands

"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. "

M

includes taxes & fees

5 Sept - 6 Sept

11. Hide-a-way

Weymouth

Kim

includes taxes & fees

1 Sept - 2 Sept

A harbor with boats docked, a building labeled 'The George Inn', and a cloudy sky.

12. Brewery View

Rodwell

Helen

includes taxes & fees

2 Sept - 3 Sept

A modern kitchen with a dining area, featuring a large window, a microwave, and a sink.

13. Coastguard Lookout

Wyke Regis

includes taxes & fees

7 Sept - 8 Sept

A row of colorful beach huts numbered 16 to 17, with a gravel path in front.

14. Bay Cottage

Rodwell

Neil

includes taxes & fees

26 Sept - 27 Sept

A marina with multiple sailboats docked along a waterfront promenade.

15. Harbour Reach 7

Weymouth

Austin

includes taxes & fees

26 Sept - 27 Sept

A room with a large window overlooking a body of water, a small table with candles, and a mirror on the wall.

16. Still Waters

Wyke Regis

Rory

includes taxes & fees

26 Sept - 27 Sept

A wooden interior with a staircase, a window with a view of trees, and a shelf with boots.

17. The Cow Shed

Dorchester

includes taxes & fees

10 Sept - 11 Sept

A wooden deck with a pergola, a table with chairs, and a brick pathway.

18. Home Waters

Wyke Regis

includes taxes & fees

10 Sept - 11 Sept

A spacious kitchen with a dining area, a grey sofa, and a vintage trunk.

19. Mermaid Cottage

Portland

Terry

includes taxes & fees

3 Sept - 4 Sept

A seaside promenade with colorful buildings, a palm tree, and a beach.

20. Wessex View

Weymouth Town Center

Kimberley

includes taxes & fees

13 Sept - 14 Sept

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Top Winterbourne Steepleton Hotel Reviews

George Albert Hotel & Spa

10/10 Excellent

"Really good stay high standards maintained throughout without being intrusive"

Pen Mill Hotel

10/10 Excellent

"From the moment I walked in the door this hotel gave me a brilliant experience. A really friendly welcome and check-in process. The room was no frills but a really comfortable bed and a large bathroom with very nice towels providing plenty of room to dry off after the shower. Ate in the restaurant and again every member of staff were helpful, attentive and welcoming which was just what I needed after a long day and being on my own. The food was also really very good as well. In the morning the breakfast was cooked fresh and loads of choice. Breakfast bap was perfect for me but I will definitely have the cooked breakfast next time. I will certainly return as felt the overall experience was very good value for money."

Sleeping Bear Hotel Dorchester

10/10 Excellent

"We arrived late at the Sleeping Bear Hotel and the self check-in was incredibly easy and smooth. We simply pressed the green button by the door and followed the instructions. Walking through the hallway, staircase and lovely sitting/living room area with my daughter, we were pleasantly surprised by how beautiful and cosy everything looked. There were lots of comfortable sofas with cushions, making it feel just like home, and we loved that we could make coffee from the machine whenever we wanted. Our room was very clean and cosy, and the mattress was unbelievably comfortable and soft. At check-out, the two lovely ladies at reception even found me a takeaway cup so I could take my coffee with me. A truly wonderful stay — I will definitely be coming back!"

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"Very nice hotel in a great location, room was more than adequate for our needs, just a couple minor faults in bathroom, a damp smell & shower head holder needed replacing as didn’t keep head in place, all the staff were excellent but a special shout out to Charlie who checked us in & was so cheerful & full of useful information about Weymouth to make our break even more enjoyable, he’s a huge asset to your hotel."

Find out more about Winterbourne Steepleton

Everything you need to know about Winterbourne Steepleton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winterbourne Steepleton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winterbourne Steepleton holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterbourne Steepleton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterbourne Steepleton holiday rentals we have selected for you start as low as NZ$398 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winterbourne Steepleton rentals

At Expedia, we put the best Winterbourne Steepleton holiday 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 holiday.

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 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 are some of the best holiday rentals that Winterbourne Steepleton has to offer?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: This holiday home rental outside of Winterbourne Steepleton comes with WiFi so that you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop and a microwave.

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

While exploring the area, visit family-friendly sights like SEA LIFE Centre Weymouth, or get outside and enjoy nature at Dorset and East Devon Coast. Tutankhamun: The Exhibition and West Bexington 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.

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Check prices for these dates

Our top choices for Winterbourne Steepleton holiday rentals

1. The Little Cottage

2. Streamside Apartments

3. Yeovil 1-bed Annex Sleeps 2 With Wifi

4. Badgers Cottage

5. The Coach House - Trinity Lodge

6. 2 Bathsheba Terrace

7. Way's Forge

8. The Old School House

9. Beach View House

10. Marina Vista

11. Hide-a-way

12. Brewery View

13. Coastguard Lookout

14. Bay Cottage

15. Harbour Reach 7

16. Still Waters

17. The Cow Shed

18. Home Waters

19. Mermaid Cottage

20. Wessex View

Find holiday rentals that suit your style

Top Winterbourne Steepleton Hotel Reviews

George Albert Hotel & Spa

Best Western Weymouth Hotel Rembrandt

The Jubilee Hotel East- with Spa Facilities

Pen Mill Hotel

The Bull Hotel

Crown Hotel

Sleeping Bear Hotel Dorchester

Heights Hotel

The Jubilee Hotel West- with Spa Facilities

Find out more about Winterbourne Steepleton

Frequently asked questions

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