Holiday houses in Chalmington

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Top-rated holiday rentals in Chalmington

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Top Guest favourite
The charming exterior of a Grade 1 listed cottage is presented, showcasing a white facade with traditional windows. Stone pathing and stone planters filled with greenery add to the welcoming appearance. The neighboring cottages feature historic architectural details, enhancing the village's character.
Cottage in Cerne Abbas
4.97 out of 5 average rating, 104 reviews

Pilgrims Cottage-Luxury Grade 1 Listed cottage

Take it easy at this unique and tranquil getaway. Come and unwind in our Grade 1 listed cottage set in the most beautiful street in gorgeous Cerne Abbas. Steeped in history you won’t want to leave this hidden gem. Out the front door are walks for miles and a visit to the Giant is a must! Then either cook up a storm in the well equipped kitchen , enjoy the garden with Big Green Egg bbq or wander down to the choice of three local pubs. The Sea is just a short 30 mins drive. Parking free opposite

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Superhost
A wooden deck surrounds an exclusive wood-fired hot tub, which produces gentle steam against a backdrop of the setting sun. An expansive view of the cider orchard is visible, framed by trees under a softly lit sky transitioning to twilight.
Shepherd’s hut in Chalmington
4.96 out of 5 average rating, 247 reviews

Stargazer, off grid shepherds hut in cider orchard

Our bespoke, self contained shepherds hut is sat looking over our beautiful cider orchard in the heart of Dorset complete with its own outdoor fire pit/bbq and exclusive wood fired hot tub. We have a range of produce to offer guests to cook in the hut or on the bbq outside and a farm shop selling our ciders, meat and local produce. There are great pubs, breweries and restaurants in the locality to enjoy plus cycle routes and walks for all abilities with stunning views of the Dorset countryside

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Top Guest favourite
The cottage, constructed from Portland stone with a thatched roof, is framed by a well-maintained garden. The exterior features multiple windows and a welcoming entrance, surrounded by neatly arranged flower beds and green lawns, presenting a serene countryside setting.
Cottage in Chilfrome
4.98 out of 5 average rating, 107 reviews

Beautiful 2 bedroom cottage in glorious Dorset

Nestled in the picturesque Dorset countryside, this charming Portland stone cottage offers a quintessential English retreat. Set within the grounds of a historic Old Rectory, the property is surrounded by rolling hills, lush meadows, and the tranquil River Frome, providing an idyllic spot for a holiday. It is all on one level,we are able to rent out the whole cottage also which creates an additional 2 bedrooms for extended family - we rarely rent this out to another party and is mostly empty.

LocationFamilyCleanliness

Guest favourite
The exterior of the lodge features a modern, dark wooden facade with large glass doors that open into the main living area. A spacious patio area is surrounded by landscaped gardens, with decorative plants and seating arrangements for relaxation.
Home in Leigh
4.94 out of 5 average rating, 350 reviews

Luxurious rural retreat

The Lodge at Willen Farm is a beautiful single level converted barn on the outskirts of the quiet village of Leigh, just 4 miles from the town of Sherborne in Dorset. The Lodge provides the perfect location for a relaxing escape to the rural countryside, yet just 40 minutes from the fabulous Jurassic coastline. Spacious accommodation with two double bedrooms, one with en-suite shower/toilet and a separate bathroom. Contemporary style with an outside patio area. Parking and a small garden area.

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Top Guest favourite
A cozy sitting area features a plush olive green velvet sofa adorned with patterned and solid cushions. A stylish wooden chair complements the vintage aesthetic, while large artworks decorate the walls. Exposed wooden beams add character, and a patterned rug enhances the inviting ambiance.
Barn in Dorset
5.0 out of 5 average rating, 135 reviews

Artist’s Creative Hideaway & Sauna

Beautiful, inspiring, and peaceful, Arthouse is a place to escape. This converted art studio in West Dorset is close to Chesil Beach and the Jurassic Coast. It is surrounded by wildflowers and features contemporary art and sculptures by artists Rouwen and Reeve. The space is complemented by mid-century modern furnishings, high ceilings, and exposed beams. All doors open to a private patio and a naturalistic garden. The Sauna, located in the gravel garden looks out onto sculptures and plants.

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Superhost
A shepherd's hut is nestled in a lush green landscape, framed by rolling hills. The sky showcases a stunning sunset with shades of orange and blue, while the fire pit and wood-fired hot tub are visible in the foreground, inviting cozy outdoor gatherings.
Shepherd’s hut in Chalmington
4.86 out of 5 average rating, 14 reviews

Supernova, off grid shepherds hut in cider orchard

Our bespoke, self contained shepherds hut is sat looking over our beautiful cider orchard in the heart of Dorset complete with its own outdoor fire pit/bbq and exclusive wood fired hot tub. We have a range of produce to offer guests to cook in the hut or on the bbq outside and a farm shop selling our ciders, meat and local produce. There are great pubs, breweries and restaurants in the locality to enjoy plus cycle routes and walks for all abilities with stunning views of the Dorset countryside.

LocationAmenitiesView

Superhost
The exterior of the barn reveals a charming blend of traditional stonework and wooden features, characterized by a large front door and multiple windows. Surrounding the entrance are well-maintained plants and shrubs within a curved brick border, contributing to a welcoming appearance.
Barn in Dorset
4.92 out of 5 average rating, 215 reviews

Lynchett Chase Barn in beautiful West Dorset

This Dorset stone barn has been modernised to provide spacious, open plan living. The property is ideal for large family holidays, and celebrations. The ample rear garden has a games room with table tennis table, perfect for children to let off steam! The barn is situated in the pretty village of Maiden Newton, which has great local shops and eating within a 5 minute walk and is just 30 minutes from the stunning Jurassic Coast, with the beautiful Dorset countryside right on the doorstep.

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Top Guest favourite
A charming stone cottage is framed by lush greenery and vibrant flowering plants. The structure features a sloped roof with three windows reflecting natural light, while decorative elements adorn the exterior, offering a welcoming view of the serene countryside.
Home in Chalmington
4.94 out of 5 average rating, 69 reviews

Rural Dorset Retreat

Escape to the heart of the Dorset Countryside, a charming accessible rural retreat surrounded by rolling hills and picturesque villages. Thoughtfully designed with disabled access, it offers cosy interiors, a log burner, and peaceful outdoor space, it's perfect for relaxing or exploring scenic trails. Wake to birdsong, dine al fresco or visit nearby historic towns and stunning coastlines. Whether you seek adventure or tranquility, Chalmington offers the perfect escape for a restful getaway.

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Top Guest favourite
A charming wooden hut is nestled among greenery, framed by a tree branch and vibrant foliage. The entrance is visible, adorned with a circular decorative piece. Lush grass surrounds the hut, contributing to the serene garden setting.
Hut in Cattistock
4.94 out of 5 average rating, 104 reviews

Private Garden Glamping Retreat- Firepit & Massage

The rustic glamping hut (double or twin) is nestling in the garden of this charming Georgian house in a tranquil Dorset village. Within a couple of steps is the bathroom hut with shower & toilet. Then there is the ‘firehut’, with a raised firepit, basic cooking equipment, fridge, microwave, toaster and mini stove. The walled garden is private for yourselves to enjoy, with an additional firepit for those starry nights. Additional two double bedrooms in main house available for booking.

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Top Guest favourite
A rustic log burning stove is positioned beside a charming stone wall, offering a cozy focal point. A woven rug covers the floor, leading to a dining area with a light-colored table and soft seating, inviting relaxed gatherings.
Cottage in West Coker
4.93 out of 5 average rating, 238 reviews

Little Gem Somerset Cottage

Little Gem Cottage is situated in the pretty village of West Coker just a ten minute drive from the A303. The village has a grocery shop, butcher, restaurant, pub, children’s playground and lots of walking all close by. The cottage is the perfect retreat and base to visit all Somerset and Dorset has to offer. There are two double bedrooms offering accommodation for upto 4 guests. The cottage garden is the perfect spot for your morning coffee or evening glass of wine by the fire pit.

ValueFamilyCheckout

Top Guest favourite
A former aircraft, showcased in a woodland setting, features a unique exterior design with vibrant green accents. The fuselage stands on a grassy area, surrounded by trees and green foliage, with a pathway leading up to it, indicating accessibility to the entrance.
Plane in Somerset
4.99 out of 5 average rating, 145 reviews

No Snakes on this Plane!

Tired of economy class? Charter a stay in a first class fuselage with wood fired hot tub situated in tranquil woodland. Welcome onboard your own private aircraft, step inside to the sleek contemporary interior of first class. Outside, unwind in seclusion in private woodland, a short walk away from the West Somerset Railway and the AONB of the Quantock Hills. An ideal getaway for two in first class, for families there is a bunk bed in the living room area. Dogs at additional cost.

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Top Guest favourite
Guest suite in Somerset
4.99 out of 5 average rating, 111 reviews

The Ops Room, Ground floor 2 bed Apartment

Observatory House is a converted cold war nuclear bunker. **** We are currently having our roof replaced but this work is overrunning Due to this we have scaffolding erected across the front of the building. If you book we will send a reduced price option to you to accept/decline as a gesture of goodwill for any inconvenience caused****. Pin coded lock box allows flexible self check-in and out so you can come and go as you please. Pets allowed but no cats due to allergies

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Popular amenities for Chalmington holiday rentals