Winterbourne Steepleton holiday homes

We found 974 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Winterbourne Steepleton that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you need and want for your stay, which might include a garden and hot tub. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winterbourne Steepleton

Showing deals for:6 Nov - 13 Nov

Interior
Our house is at the entrance to the grounds.
Dorset Alpaca Shepherd's Hut was built to our specification, and is spacious!
There is inside dining or 'al fresco' dining at the shepherd's hut.
Exceptional
(42 reviews)

REALLY luxurious pair of shepherd's huts, overlooking our alpacas!

Dorchester

9% off
NZ$1,629
for 7 nights, 1 cabin
NZ$233 per night
includes taxes & fees
REALLY luxurious pair of shepherd's huts, overlooking our alpacas!
Inside The Shepherd’s Hut at ‘The Hide’
The Wood Fired Hot tub and an evening sunset!
The Shepherd’s Hut at ‘The Hide’
Inside the Cabin at The Hide
Exceptional
(55 reviews)

The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard

Weymouth

8% off
NZ$2,794
for 7 nights, 1 cabin
NZ$399 per night
includes taxes & fees
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
Double bedroom
Exterior
Outdoor dining
Kitchen
Wonderful
(46 reviews)

Pretty Cottage Close To The Dorset Coast.

Weymouth

23% off
NZ$1,564
for 7 nights, 1 cottage
NZ$223 per night
includes taxes & fees
Pretty Cottage Close To The Dorset Coast.
Living area
Jungle room
Double bed
Dining
Outdoor dining
Wonderful
(35 reviews)

A charming seaside cottage 5 minutes walk from beach on Jurassic Coast

Weymouth

20% off
NZ$7,764
for 7 nights, 1 home
NZ$1,109 per night
includes taxes & fees
A charming seaside cottage 5 minutes walk from beach on Jurassic Coast
Grade II listed bay front
Room
Dining
Private kitchen
Excellent
(9 reviews)

5 bed, 5 bath, Slps 18, Town Ho. 60 yds Weymth beach & harbour, NEWLY RENOVATED!

Weymouth

9% off
NZ$5,426
for 7 nights, 1 home
NZ$775 per night
includes taxes & fees
5 bed, 5 bath, Slps 18, Town Ho. 60 yds Weymth beach & harbour, NEWLY RENOVATED!
Exterior
Our herd of 19 alpacas live in our field opposite the cottage (but CAN stray!)
Room
Property grounds
Exceptional
(157 reviews)

Beautifully appointed west Dorset Cottage With Open Parkland Views

Dorchester

9% off
NZ$1,672
for 7 nights, 1 cottage
NZ$239 per night
includes taxes & fees
Beautifully appointed west Dorset Cottage With Open Parkland Views
Living area
Living area
Room
Private kitchen
Wonderful
(36 reviews)

Apartment near the beach with private parking and pet friendly

Weymouth

17% off
NZ$1,213
for 7 nights, 1 apartment
NZ$173 per night
includes taxes & fees
Apartment near the beach with private parking and pet friendly
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Winterbourne Steepleton getaway

Learn about the unique charm of Winterbourne Steepleton with a stay in a holiday home rental. This city has something for everyone. Weymouth Beach and Durdle Door are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Winterbourne Steepleton

Are you hoping to discover attractions to see during your stay? Venture out of your holiday home and check out everything that makes Winterbourne Steepleton a fun place to get away to. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Abbotsbury Swannery (4.1 mi / 6.7 km)
  • Warmwell Holiday Park Ski Slope (8.8 mi / 14.1 km)
  • Bridport and West Dorset Golf Club (8.9 mi / 14.4 km)
  • Monkey World Ape Rescue Center (14.2 mi / 22.9 km)
  • Charmouth Heritage Coast Centre (15.9 mi / 25.6 km)
  • SEA LIFE Centre Weymouth (6.7 mi / 10.8 km)

Exploring the natural features in Winterbourne Steepleton

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Winterbourne Steepleton is a great spot to appreciate mother nature. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Weymouth Beach (7.4 mi / 11.9 km)
  • Durdle Door (12.8 mi / 20.7 km)
  • Abbotsbury Sub-Tropical Gardens (4.2 mi / 6.8 km)
  • Dorset and East Devon Coast (5 mi / 8.1 km)
  • West Bexington Beach (5.8 mi / 9.3 km)
  • Bowleaze Cove Beach (6.9 mi / 11.1 km)

Transport to and around Winterbourne Steepleton

Fly into Bournemouth (BOH-Bournemouth Intl.), the closest airport, located 31.5 mi (50.6 km) from the city centre.

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 Weymouth Beach. Durdle Door and Abbotsbury Sub-Tropical Gardens 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.