Winterbourne Steepleton Vacation Rentals from $236: Search Short-Term Rentals

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Our top choices for Winterbourne Steepleton vacation rentals

1. The Little Cottage

Weymouth

Lea

$656 nightly

Sep 2 - Sep 3

Total with taxes and fees

Apartment, Ensuite, Garden View | Lounge

2. Streamside Apartments

Yeovil

Anonymous traveler

$185 nightly

Sep 8 - Sep 9

Total with taxes and fees

3. Yeovil 1-bed Annex Sleeps 2 With Wifi

Yeovil

Leigh

$77 nightly

Sep 1 - Sep 2

Total with taxes and fees

4. Badgers Cottage

Weymouth

Neil

$588 nightly

Sep 3 - Sep 4

Total with taxes and fees

5. The Coach House - Trinity Lodge

Dorchester

Steffen

$402 nightly

Sep 4 - Sep 5

Total with taxes and fees

6. 2 Bathsheba Terrace

Dorchester

Rachael

$496 nightly

Sep 23 - Sep 24

Total with taxes and fees

7. Way's Forge

Dorchester

Virginia

$585 nightly

Sep 2 - Sep 3

Total with taxes and fees

8. The Old School House

Dorchester

NIGEL

$640 nightly

Sep 5 - Sep 6

Total with taxes and fees

9. Beach View House

Wyke Regis

Arve Moen

$825 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

$758 nightly

Sep 5 - Sep 6

Total with taxes and fees

11. Hide-a-way

Weymouth

Kim

$468 nightly

Sep 2 - Sep 3

Total with taxes and fees

12. Brewery View

Rodwell

Helen

$520 nightly

Sep 2 - Sep 3

Total with taxes and fees

13. Coastguard Lookout

Wyke Regis

$516 nightly

Sep 7 - Sep 8

Total with taxes and fees

14. Bay Cottage

Rodwell

Neil

$1,179 nightly

Sep 2 - Sep 3

Total with taxes and fees

15. Harbour Reach 7

Weymouth

Austin

$650 nightly

Sep 2 - Sep 3

Total with taxes and fees

16. Still Waters

Wyke Regis

Rory

$906 nightly

Sep 20 - Sep 21

Total with taxes and fees

17. The Cow Shed

Dorchester

$1,114 nightly

Sep 2 - Sep 3

Total with taxes and fees

18. Home Waters

Wyke Regis

$700 nightly

Sep 10 - Sep 11

Total with taxes and fees

19. Mermaid Cottage

Portland

Terry

$563 nightly

Sep 3 - Sep 4

Total with taxes and fees

20. Wessex View

Weymouth Town Center

Kimberley

$559 nightly

Sep 13 - Sep 14

Total with taxes and fees

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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."

The Manor Hotel by Greene King Inns

10/10 Excellent

"The single room was fine and reasonable value (the doors do shut loudly). The staff were all very friendly, helpful and impressive (excepting one rather sour lady behind the bar!). They were very polite and kind, it makes a big difference to how you feel about a hotel. The food was really good and not expensive, excellent value. The drinks selection was extensive. There's plenty of outside seating. All in all, I definitely recommend the hotel and would happily stay there again."

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 $236 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?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: This vacation home rental outside of Winterbourne Steepleton comes with WiFi so 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 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.

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Check prices for these dates

Our top choices for Winterbourne Steepleton vacation 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 vacation rentals that suit your style

Top Winterbourne Steepleton Hotel Reviews

George Albert Hotel & Spa

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

The Manor Hotel by Greene King Inns

Find out more about Winterbourne Steepleton

Frequently asked questions

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