Vacation rentals in Winterbourne Steepleton

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Top-rated vacation rentals in Winterbourne Steepleton

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Guest favorite

Home in Dorset

4.93 out of 5 average rating, 91 reviews

BEACH HOUSE: sleeps 14 right on Sea / Beach / Sand

- Stunning sea and beach views: >80 reviews! - Right on beach without crossing any road - safe for children - Large 1840s period house, superbly equipped, quirky charm - Quieter end of town, exclusive use + 2 car permits - Space for several families to spread out, great privacy - Beach for a mile in both directions - Recent upgrades, was guesthouse - "Weymouth Best Beach in UK" (2023 Sunday Times) - UK's 3rd sunniest place - Harbour boat trips, sailing - Jurassic coast, unspoilt countryside

Top guest favorite

Condo in Canford Cliffs

4.96 out of 5 average rating, 69 reviews

Beach Retreat 1 - 400m to beach-Luxury 2 bed Flat

Luxury, family friendly apartment in an outstanding location with everything on your doorstep! On a quiet street in exclusive Canford Cliffs village, moments from top restaurants, bakery/deli, 2 gastropubs and Tesco. 5 min scenic woodland walk to stunning award winning Sandbanks beach and children's Pirate playground. Ideal luxury family holiday with the perfect location to park the car and enjoy the beach, watersports and entire holiday on foot. Free parking provided & no Airbnb cleaning fees!

Guest favorite

A spacious safari tent is set on a wooden deck, surrounded by greenery. The tent features a canopy roof supported by wooden poles, with a picnic table on the deck and a fire pit nearby. Gravel pathways enhance the outdoor space.

Tent in Corfe Castle

4.96 out of 5 average rating, 53 reviews

Farm glamping close to Swanage coast (2 of 5)

Glamping in one of our 5 rustic and very comfortable safari tents on our working dairy farm close to Swanage. Tents sleep up to 4 guests in a king bed, twin beds or double cabin style bed. Beds made up. Bring your own towels. Own shower room. Cook on the wood burning stove (with oven) or BBQ outside. Basic electricity providing overhead lanterns and a couple of sockets for charging mobiles. Firewood included. Dog welcome at an extra £25 (must be booked in and paid for prior to arrival)

Guest favorite

A private enclosed garden features neatly trimmed grass and vibrant greenery, providing a peaceful atmosphere. Two chairs are positioned for relaxation, with lush plants and hedges enhancing the natural surroundings. Scenic countryside views extend beyond the garden, inviting enjoyment of the outdoors.

Cottage in Upton Scudamore

4.94 out of 5 average rating, 212 reviews

*New Luxury 5 * “Cosy-Up Cottage” Near Longleat

A delightful chocolate box, cosy-up, Romantic cottage set in a charming friendly, peaceful village. Recently renovated and decorated throughout . It has so much charm and character. Bright and contemporary style. Retaining the beautiful exposed oak beams and open fire. private enclosed garden with country views. Truly romantic get away. Surrounded by stunning countryside where you can enjoy plenty of walking, cycling, bird watching, amazing views, paragliding, golf Award Winning village pub.

Top guest favorite

Home in Friars Cliff

4.99 out of 5 average rating, 203 reviews

Whole seaside apt, stones throw to the new forest.

Relax with the whole family at this peaceful & child friendly place. Well presented holiday home with exclusive use of home and private garden / patio area. A short walk to award winning Avon beach, Saltwater Sauna & Mudeford Harbour. New forest close also. ideal for a family of four, with one double bed with ensuite and premier metal action sofa bed easily made up located in the living room. Bars and restaurants are all within a short stroll. Explore / relax in this bright comfortable annexe.

Guest favorite

A modern dining area is displayed with wooden chairs arranged around tables set with white tablecloths. Floor-to-ceiling windows offer a view of the water and distant boats, allowing natural light to fill the space.

Home in Parkstone

4.88 out of 5 average rating, 172 reviews

Cottage close to beaches and restaurants

A beautiful two bed house with garden and off street parking in an excellent location in Poole Dorset. The property features a new luxury bathroom installed in June 2021. There is an additional double sofa bed in the second living room. The property is moments from popular Ashley Cross with its bustling bars and restaurants and only a five minute drive to the award winning beaches of Sandbanks and Branksome Chine. Guests also have the open spaces of Poole Park only 5 minutes walk away.

Guest favorite

Cottage in Kingston Deverill

4.92 out of 5 average rating, 165 reviews

Kings Cottage - Heart of the Deverills - EV Point

Experience Kings Cottage in Kingston Deverill, a 17th-century thatched gem harmonizing historic charm with modern comforts. Nestled by the River Wylye in an Area of Outstanding Natural Beauty, it invites hikers, cyclists, and explorers. Nearby attractions like Stourhead and Longleat add allure. This tranquil village, with a rich 4,000-year history, offers quiet pubs, historic sites, and timeless countryside beauty. A perfect retreat equidistant from Bath, Salisbury, and Stonehenge.

Superhost

A private entrance is framed by stone pillars topped with blue spheres. The pathway leads through lush green grass towards the sea, lined with tall, slender trees under a partly cloudy sky. The openness invites exploration towards the Short House.

Cottage in Bridport

4.9 out of 5 average rating, 122 reviews

5* Cottage on Chesil Beach Dorset Jurassic Coast

SHORT HOUSE, CHESIL BEACH; beautiful 'Switch off the world', 5* Seaside Cottage on Dorset's World Heritage Jurassic Coast. Private access to Chesil Beach; 400m. Dogs welcome. Spectacular ocean views, dining terrace, large living space, fully equipped kitchen, 2 double ensuite bedrooms, king size (or twin) beds, Egyptian linen, fluffy towels & sandpit in a lovely garden. 43" Sony UHD TV + SKY Q, DVD & Bose Sound. A peaceful place to isolate, recuperate & build sandcastles.

Superhost

A private hot tub sits on a wooden deck, offering views of the expansive grassy landscape. In the distance, a children's play structure stands amidst the serene countryside, under a clear blue sky with scattered clouds.

Cottage in Blandford Forum

4.84 out of 5 average rating, 323 reviews

Ranmoor Estate - Kestrel Lodge - Hot Tub & A/C

Experience the charm of a unique, pet-friendly glamping lodge featuring two cozy bedrooms. Enjoy the luxury of private hot tubs and a barbecue on your patio, perfect for relaxing evenings under the stars. This fully air-conditioned retreat comes equipped with a modern kitchen, complete with a fridge, ensuring you have everything you need for a comfortable stay. Each room is fitted with smart TVs, providing entertainment at your fingertips for a delightful getaway.

Guest favorite

A secluded cabin, partially hidden by lush greenery, offers a serene escape. Surrounding the cabin, a mix of wildflowers and tall trees creates a natural setting. Outdoor furniture, including a table and seating area, is arranged on a grass path, inviting relaxation in nature.

Hut in Dorset

4.96 out of 5 average rating, 111 reviews

Secret cabin by stream in lovely wild garden

Enjoy a magical stay in our secret cabin, situated in our award-winning wild garden beside a lovely stream. This storybook cabin is nestled in nature but is also in the heart of the pretty small town of Beaminster. It offers the best of both worlds when it comes to glamping! Venture out to pubs and restaurants in easy walking distance and return to the sound of an owl hooting. The perfect base for exploring the countryside and coastline of beautiful West Dorset.

Superhost

An open-plan kitchen and dining area features modern appliances and a sleek countertop with four black bar stools. A cozy grey sofa is positioned against a wall adorned with artwork. Natural light brightens the space through multiple windows.

Condo in East Southbourne

4.85 out of 5 average rating, 107 reviews

The White House - Lux Southbourne beach 3 bed stay

Relax with the whole family at our peaceful apartment. [*] Newly renovated and lovingly refurbished art deco apartment. [*] 2 minutes walk from 9 miles of Dorset blue flagged sandy beach. [*] Top class modern finish. [*] Luxury, three bedroom modern apartment. [*] Ideal for families, couples and remote working. With access to Fast Wifi and Netflix, you can really make yourself at home. If you have any questions about our family run apartment,let us know!

Guest favorite

A light-filled living area features a cozy sofa adorned with decorative cushions. A wooden coffee table holds a book and two glasses beside a bottle of wine. Bi-fold doors open to a well-maintained garden, offering a glimpse of greenery and flowering plants outside.

Home in Tisbury

4.98 out of 5 average rating, 118 reviews

Spacious 4-bedroom holiday home in Tisbury

Beech House is a new, stone-built 4-bedroom house with a large open-plan living area and beautiful views over rooftops to the countryside beyond. Nestled in the heart of the popular small town of Tisbury, it’s a convenient stroll away from high-street shops, pubs and the train station. Despite its central location, the house is tucked away just off a quiet lane, making it wonderfully peaceful and homely.