Holiday rentals in Crossways

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Top-rated holiday rentals in Crossways

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Top guest favourite
A luxury hot tub filled with bubbling water welcomes relaxation, framed by lush greenery and open fields under a clear blue sky. The spacious area includes a basketball hoop for added enjoyment, creating an inviting outdoor atmosphere.
Guest house in Tarrant Gunville
4.88 out of 5 average rating, 208 reviews

The Retreat ~ Hot Tub~ Sauna ~ Charming & Cosy Gem

Step into the stylish and comfortable 1BR 1Bath guest house nestled in the picturesque village of Tarrant Gunville. It offers a relaxing oasis with a luxury hot tub, sauna, and a perfect base to explore natural attractions and historical landmarks of Dorset County. Modern design and a rich amenity list will satisfy your every need. ✔ Comfy BR with a Double Bed ✔ Bright Living Space ✔ Kitchenette Amenities ✔ Garden ✔ Hot Tub ✔ Sauna ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Parking See more below.

ValueFamilyAir conditioning

Top guest favourite
A functional open-plan space features a well-equipped kitchen with green cabinet fronts and modern appliances. A dining table and chairs are set nearby. A cozy sleeping area is marked by a four-poster bed, complemented by natural wood flooring and soft decor elements.
Guest suite in Crossways
4.97 out of 5 average rating, 143 reviews

The Annex @14

Welcome to The Annex @14, a newly renovated ground floor property and great base for exploring historic Dorset and a perfect getaway for two! Self-contained with its own private entrance .The annex is attached to our home at the end of a quiet cul-de-sac in the village of Crossways near Dorchester. There is a hot tub available for your own exclusive use! In the heart of Hardy Country, ideal for walkers and cyclists. Lulworth Cove, Durdle Door, the beautiful sands of Weymouth Bay are close by.

LocationFamilyGetting around

Guest favourite
The exterior of the Victorian Reading Room is presented, showcasing a charming brick facade with light moss present on the roof. A welcoming entry door, framed by two chimneys, is complemented by modern windows. A vintage-style post box is positioned beside the entrance.
Tiny home in West Stafford
4.92 out of 5 average rating, 293 reviews

The Old Reading Room West Stafford, Dorset.

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

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Guest favourite
Holiday park in West Lulworth
4.95 out of 5 average rating, 118 reviews

Sea View Chalet - Durdle Door

Our Chalet is a treasured home away from home, overlooking stunning Durdle Door, a World Heritage Site on the beautiful Dorset Jurassic Coast…. The chalet has a large decking overlooking the sea, it’s a total escape…..it has 1 King Double bedroom with en-suite, & 1 twin, 2 shower rooms & fully fitted modern kitchen/living area which opens onto the large decking area and panoramic views of the sea… to the left is Lulworth Cove, to the right the Isle of Portland, amazing sunrises and sunsets!

LocationFamilyAmenities

Guest favourite
Bus in Owermoigne
4.87 out of 5 average rating, 318 reviews

Fun Bus family playground woodburner dogs nr beach

Escape to a beautiful vintage bus, set in the enchanting grounds of a 13th-century moated manor house. Fully equipped with kitchen, wood burner, solar power, and private shower & compost toilet nearby. Enjoy a private garden with fire pit, plus access to a huge shared garden, treehouse, trampoline & fire pit. Just 10 mins from the Jurassic Coast & 15 mins from Weymouth Beach. A perfect family getaway, and well-behaved pets are welcome! Also available: vintage horsebox, woodland hut & yurt.

LocationFamilyCheckout

Top guest favourite
A cozy bedroom is presented with a wooden bed featuring crisp white linens and decorative pillows. A light-colored dresser is positioned nearby, complemented by a small lamp. Natural light filters in through patterned curtains, enhancing the serene atmosphere.
Tiny home in Dorset
5.0 out of 5 average rating, 210 reviews

Cosy private Loft overlooking Dorset countryside

Nestled in the heart of the Dorset countryside, The Loft is your ideal 'getaway'. From stunning views to a comfy king-size bed, this cosy space will provide you with everything you need to relax. Open the stable door, and listen to the birds, reconnect with nature while sipping coffee and tucking into a selection of breakfast options provided upon your arrival. With an abundance of local amenities, please see the guide for my favourite secret spots! We look forward to welcoming you!

ValueLocationHospitality

Top guest favourite
The entrance features a charming brick façade with large windows, allowing natural light to fill the space. A wooden bench is positioned near the front door, surrounded by potted plants that enhance the welcoming ambiance.
Cottage in Dorset
5.0 out of 5 average rating, 94 reviews

No1. The Courtyard, Clyffe House

Enjoy a tranquil break in our recently renovated Grade II listed cottage in the heart of Dorset. No.1 The Courtyard is nestled just outside the village of Tincleton and was originally part of the servant’s accommodation to Clyffe House (1842). We are situated 6 miles from Dorchester, and within easy reach of many Dorset attractions; Lulworth Cove, Durdle Door, Corfe Castle, The Purbeck Hills, Kimmeridge, Southwest Coastal Path, Bovington Tank Museum, Monkey World, Weymouth, Swanage.

LocationFamilyCleanliness

Top guest favourite
A private garden features a round table surrounded by four chairs, set on a stone patio. Lush greenery and flowering plants border a well-maintained lawn, while a rustic shed is visible in the background under a clear blue sky dotted with clouds.
Cottage in Lewell
4.94 out of 5 average rating, 319 reviews

Jasmine Cottage

Jasmine Cottage is a characterful, compact barn conversion, that sits next to the 400 year old farm house. It sleeps up to four people (including infants), with a double and a twin room. We are one mile away from The Wise Man Inn - an award-winning pub; 6 miles from Dorset's stunning Jurassic coast and 3 miles from the county town of Dorchester. You will, however, need a car- or bikes! Sorry, no pets and no smoking. No EV charging, yet, but there are many fast charging points nearby.

FamilyValueGetting around

Top guest favourite
The exterior of the barn features a heart-shaped wooden accent on the entrance, surrounded by two planters with neatly trimmed shrubs. A pathway of stone slabs leads through a grassy area adorned with round stones and blooming flowers, set against a backdrop of large windows.
Barn in Dorset
4.99 out of 5 average rating, 149 reviews

Coppice Barn, farm stay, nr Durdle Door & Lulworth

Sorry no Pets Suitable for only one infant. A barn conversion two miles from the Dorset coast. Set within its own private garden with unspoilt views of Galton Farm overlooking Moreton forest and Tadnoll Heath. Ten minutes drive to Durdle Door, Lulworth Cove and Ringstead Bay. Plenty of coastal and country walks to choose from. The barn consists of one bedroom with a superking bed. Large bathroom and open plan kitchen, dining and sitting area all delightfully decorated.

LocationValueOutdoor spaces

Guest favourite
An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.
Cottage in Dorset
4.97 out of 5 average rating, 395 reviews

Private use of Indoor Pool available May- end Sept

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

LocationFamilyHospitality

Top guest favourite
The image depicts a roundhouse surrounded by a gravel garden with various plants. A wooden bench is positioned in the foreground, while a fire pit is visible. The outdoor deck features seating and a log burner, with clear blue skies in the background.
Place to stay in North Curry
4.99 out of 5 average rating, 145 reviews

Luxury Roundhouse with log fired hot tub

A bespoke, luxury roundhouse, with log fired Skarsguard hot tub & stunning views of the Blackdown Hills and surrounds. Nestled above the Somerset Levels. The Good Life’s roundhouse is the perfect place to get away from it all and enjoy some quiet time in the country. Come for a romantic getaway, just the two of you, unwind & destress, with luxurious and private surroundings.

FamilyLocationHospitality

Top guest favourite
A well-lit room features a sloped ceiling with a skylight providing natural light. A wooden table with two folding chairs is positioned beside a small television on a stand. An open doorway leads to a separate sleeping area with a neatly made bed and patterned bedding.
Guest suite in Crossways
4.95 out of 5 average rating, 375 reviews

Self contained flat in quiet residential close.

We are situated in a village close to the Jurassic Coast and a short distance from Dorset's county town Dorchester. We offer a self contained annex to our house. It has one bedroom, a bathroom and living area with kitchenette. There is a large parking area and we benefit from a local railway station with connections to London and Weymouth and local bus service.

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Popular amenities for Crossways holiday rentals