Vacation rentals in Shillingstone

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Top-rated vacation rentals in Shillingstone

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Guest favorite

Cottage in Shroton

4.93 out of 5 average rating, 169 reviews

Beautiful Restored Cottage in the heart of Dorset.

A stunning, newly refurbished and tranquil, Dorset holiday cottage. Old School Cottage was built in 1851, and was originally part of the village school. Nestled at the foot of Hambledon Hill, in the village of Shroton, rural rambles are a few steps from the front gate! All the landscape photos shown are only a few metres from the cottage. This is a beautiful place to stay, with a stunning review record. www.oldschoolcottagedorset.co.uk https://www.instagram.com/oldschoolcottagedorset/

Feb 1 – 8

G$32,041 GYD per night

Guest favorite

Cottage in Dorset

4.9 out of 5 average rating, 147 reviews

33 - Grade II 3 bedroom cottage in charming town

A charming Grade II listed cottage in the hub of Sturminster Newton with amenities such as Butchers, Bakers , Newsagents, Pubs & Restaurants. Easy access to countryside offering stunning walks on Dorset Trail way & Jurassic Coast within 1 hour's drive. Comfortable accommodation for up to 6 guests, The cottage comprises fitted kitchen, dining room and sitting room with wood burning stove, ground floor cloakroom, upstairs 3 bedrooms and 3 bathrooms over two floors and sheltered backyard

Oct 6 – 13

G$39,486 GYD per night

Guest favorite

Tiny home in Fontmell Magna

4.93 out of 5 average rating, 192 reviews

Cosy cottage for 2

Entire cottage to yourselves. Light and airy accommodation on one floor. Cosy and comfy sitting area (Freeview TV), WIFI. fully fitted kitchen, bedroom (Kingsize bed), shower room and dressing room. Direct access via French doors to a pretty garden. Parking is on the lane outside. Perfect for a weekend or mid-week getaway. Please note this property is for a maximum of two adults and is not suitable for children or babies. Dogs usually accepted but please check with owner prior to booking.

Jan 28 – Feb 4

G$22,711 GYD per night

Guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 153 reviews

Lovely cosy place to stay in the heart of Dorset

Oak Tree Barn is a self-catering holiday accommodation in the heart of the village of Hazelbury Bryan, Dorset. The conversion was completed in early 2012 using locally reclaimed materials and keeping many of the original features. The Barn is warm and cosy in winter and cool in summer, the detached Barn has a large open-plan lounge and kitchen with views towards the local hills. The two bedrooms (one double with bath, one twin with shower) overlook paddocks where sheep graze and chicken forage.

Oct 23 – 30

G$25,917 GYD per night

Guest favorite

Home in Dorset

4.97 out of 5 average rating, 230 reviews

The Barn @ Star Farm

Set in the heart of the Blackmore Vale in rural North Dorset, The Barn@Star Farm is a spacious 2 bedroom self catering holiday let furnished and equipped to a high standard. Recently converted the barn has its own private track and has wonderful views over unspoilt farmland. The property is quietly on the outskirts of the village of Hazelbury Bryan and is within a 45 minute drive to the Dorset Coast. The market towns of Sherborne, Blandford Forum and Dorchester are all within 20 minutes drive.

Jan 8 – 15

G$27,865 GYD per night

Guest favorite

Place to stay in Cann Common

4.97 out of 5 average rating, 223 reviews

The Barn - peaceful country setting.

A converted barn at Cann Common next to the main house with its own garden, patio and parking area. Located on a no-through road with only local residents traffic, giving a peaceful setting with views of the surrounding hills. Shaftesbury just over a mile with its historic Gold Hill and a good choice of shops and places to eat. It is a good base for exploring the area, offering historic houses, interesting gardens, walks, the Jurassic Coast, Stonehenge, Salisbury and Bath and much more.

Jan 31 – Feb 7

G$22,835 GYD per night

Guest favorite

Tiny home in Blandford Forum

4.82 out of 5 average rating, 124 reviews

Garden lodge retreat direct access to Hod Hill

We look forward to your visit. The self contained Garden Lodge with ONE double SOFA BED leads directly onto the Irwene River path to Hod Hill and walks to Hambledon Hill. It’s heated and cosy. The kitchen has a toaster, coffee machine, cooker, microwave, fridge, sink, pots pans, cutlery crockery, salt & pepper. Plus iron and hair dryer. There are cycle trails, and you can walk, run or cycle the Trailway to Blandford Forum. It’s a short drive from Shaftsbury Poole Harbour, and Wareham

Feb 8 – 15

G$10,111 GYD per night

Guest favorite

Condo in Hilton, Blandford Forum

4.96 out of 5 average rating, 118 reviews

Stylish self-contained annexe in rural mid Dorset

A thoughtfully designed space for two in glorious, peaceful Dorset countryside. Located on the edge of the lovely village of Hilton, this is a perfect place to hunker down for a few days or to use as a base for exploring all the amazing places that Dorset has to offer all within easy reach. We are gentle half hour stroll from Milton Abbey which is set in a magnificent Capability Brown landscape. We are also an easy trip (approximately 20 miles) from the spectacular Jurassic coast.

Apr 20 – 27

G$22,809 GYD per night

Guest favorite

Guesthouse in Winterborne Stickland

4.89 out of 5 average rating, 171 reviews

Pretty Self-Contained Thatched Annexe in Dorset

Rosebud is a beautiful little cottage! It is a part of a large 18th Century thatched cottage set in the heart of beautiful North Dorset countryside, ideal for a peaceful getaway for two people . We are approx. 30 minutes from the Purbecks and Poole. Rosebud is newly refurbished with all the facilities you should require during your stay with us. We are very happy to help with any local advice as we love this part of the world and are pleased to be able to share it with you.

Sep 26 – Oct 3

G$27,823 GYD per night

Guest favorite

Apartment in Droop

4.89 out of 5 average rating, 138 reviews

Locketts - self-contained stylish accommodation

Set in the heart of Dorset, we are situated close to the market towns of Sturminster Newton, Blandford Forum, Sherborne and Dorchester. With far reaching picturesque countryside views, it is also no more than forty-five minutes from the Jurassic Coast, famous for stunning beaches along the South West Coast Path. Dorset has a reputation for award-winning pubs and seafood restaurants. We're in a great spot if you want to break your journey to or on your return from Cornwall

Sep 19 – 26

G$29,644 GYD per night

Guest favorite

Condo in Child Okeford

4.94 out of 5 average rating, 150 reviews

The Willows- 2 Bedroom Ground Floor Cottage

The Willows is a two bedroom ground floor cottage in the village of Child Okeford which nestles under the iron age hill fort of Hambledon Hill. In the heart of the Dorset Countryside there are two pubs, a farm shop and café, a post office and a village shop. Child Okeford is surrounded by beautiful countryside where you will find many delightful walks. Further afield you can head to the Jurassic Coast and beautiful beaches of Poole, Bournemouth and Weymouth.

Dec 1 – 8

G$37,224 GYD per night

Guest favorite

Cottage in Okeford Fitzpaine

4.97 out of 5 average rating, 302 reviews

The Garden House Okeford Fitzpaine Dorset

The Garden House is a restored spacious 2 bedroom former 19th century Coach house, situated in the centre of an attractive rural village in the heart of the rolling North Dorset countryside. Okeford Fitzpaine, near Sturminster Newton is a picturesque, quiet and peaceful Dorset village with a shop /post office and a good local pub. A perfect destination for families, nature lovers, walkers, cyclists and anyone else wishing to escape to beautiful rural Dorset.

Jun 13 – 20

G$33,994 GYD per night