Vacation rentals in Woolland

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Top-rated vacation rentals in Woolland

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Guest favorite

Hut in Piddlehinton

4.99 out of 5 average rating, 166 reviews

Kingfisher cabin in secluded Dorset woodland

In Middlemarsh not Piddlehinton. Reconnect with nature at this lovely secluded spot, surrounded by woodland and forest, this is the perfect getaway from busy city life. The cabin is located within an area of outstanding natural beauty with access to a great range of footpaths, and the Hunters Moon Inn a short walk away. It is also only a 30 minute drive to the Jurassic coast with beaches like Lulworth. There are a herd of friendly deer on site that you can be introduced too. We do not allow dogs

Mar 21 – 28

G$20,751 GYD per night

Guest favorite

Cottage in Dorset

4.97 out of 5 average rating, 537 reviews

Cute & Cosy Bothy Cottage, near Sherborne & Yeovil

The Bothy is a stylish detached cottage where you can share some Prosecco on your terrace or snuggle up beside a log fire Dating from the 1700's, our recently restored "boutique" stone cottage is in the rural historic Yetminster Conservation Area with a thatched pub, lovely local cafe & shop. It is next door to a quintessential English Heritage listed thatched cottage You are on the edge of the Dorset Area of Outstanding Natural Beauty and you have great access to the sea on the Jurassic Coast

Sep 21 – 28

G$29,346 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$25,915 GYD per night

Guest favorite

Home in Dorset

4.96 out of 5 average rating, 232 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.

Oct 29 – Nov 5

G$27,694 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.

Aug 28 – Sep 4

G$22,807 GYD per night

Guest favorite

Guesthouse in Winterborne Stickland

4.9 out of 5 average rating, 172 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 28 – Oct 5

G$27,525 GYD per night

Guest favorite

Guesthouse in Kings Stag

4.94 out of 5 average rating, 135 reviews

The Annexe

Peaceful annexe located within the 2 acre grounds of a traditional thatched cottage . Based within a small village in the beautiful North Dorset countryside. The annexe consists of a bright and airy bedroom/ sitting room upstairs and a kitchen diner with small shower room downstairs The sitting room leads onto a large balcony overlooking a large pond and countryside views The town of Dorchester is 15 miles away with access to the Jurassic coast about a 40 minute drive away

Aug 26 – Sep 2

G$22,676 GYD per night

Guest favorite

Guest suite in Pulham

4.97 out of 5 average rating, 230 reviews

Cosy Self-Contained Annexe in Rural Dorset

Set in the heart of the Blackmore Vale, the village of Pulham is perfectly situated close to the market towns of Sherborne, Dorchester and Bridport. With far reaching picturesque countryside views, it is also no more than a half an hour drive from the Jurassic Coast where you will find many stunning beaches set along the South West Coast Path. Dorset has a well-deserved reputation for eateries, from award-winning pubs and seafood restaurants to tearooms from a by-gone era.

Jun 10 – 17

G$20,393 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

Aug 8 – 15

G$29,642 GYD per night

Guest favorite

Cottage in Okeford Fitzpaine

4.97 out of 5 average rating, 303 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 11 – 18

G$32,012 GYD per night

Guest favorite

Cottage in Henley

4.92 out of 5 average rating, 276 reviews

Shepherd's Cottage

Shepherd's cottage is a delightfully cosy annexe with it's own private entrance and own cottage garden. Tucked away on a no through road, that leads directly onto a bridleway and footpaths, Shepherd's cottage makes an ideal place to stay for those who simply want to get away from it all. We welcome 2 small dogs ( pet fee applies) and horses - with a choice of fields to keep your horse in (please note the additional charge of £30 per night for horses).

Oct 2 – 9

G$19,055 GYD per night

Guest favorite

Apartment in Stoke Wake

4.96 out of 5 average rating, 158 reviews

Willow Tree Farm Studio

Welcome to Willow Tree Farm. We have a lovely large private studio with stunning views from its own balcony across the Dorset countryside. Our space is perfect for two adults to escape the rat race and unwind. The studio has a country theme with a comfy Super King Bed, sofa, an indoor table for two, a TV as well as a large en-suite bathroom. Outside you'll find your own private balcony with garden furniture and a BBQ just down the steps below.

Jun 12 – 19

G$18,965 GYD per night