Holiday rentals in Tolpuddle

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Top-rated holiday rentals in Tolpuddle

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Guest favourite

Hut in Owermoigne

4.88 out of 5 average rating, 273 reviews

Woodland Retreat Log Cabin nr Durdle Door Weymouth

Come stay in our secluded woodland glade in your own log cabin! Bring your own bed linen. Snuggle by the outdoor fire pit. Enjoy the views across picturesque dorset countryside. Super cosy and surrounded by nature! Only 10 minutes drive to the World Heritage Jurrasic coast, Dorset's famous beaches Durdle Door and Lulworth Cove. Parking 50 metres away with compost toilet and basic outside off grid shower. Check out our Magic, Bus, Yummy Yurt, and Homely Horsebox for more luxurious accommodation.

Top guest favourite

Guest suite in Crossways

4.96 out of 5 average rating, 101 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.

Guest favourite

Guest suite in Dorset

4.91 out of 5 average rating, 219 reviews

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

Top guest favourite

Farm stay in Blandford Forum

4.94 out of 5 average rating, 103 reviews

Self-contained annexe on organic dairy farm

Whether you’re wanting to have a base for a holiday with family, staying for a wedding, or here on business, I would love to have you stay at Lower Farm. The Annexe is situated on a working organic dairy farm, nestled in the most idyllic part of Dorset; perfectly located for beaching, country pubbing or long walks in the rolling countryside that surrounds. The property has a kingsize bed and a sofa bed. I will always do my utmost to cater to your requirements, just pop me a message ☺️

Guest favourite

Tiny home in Bere Regis

4.95 out of 5 average rating, 196 reviews

Luxury thatched Little Barn

The Little Barn is a 200 year old, thatched, cob cottage. It is a self-contained studio guest room with its entrance in the garden of the main house. It is perfect for a couple using the comfortable king-sized bed. It is thoughtfully decorated and furnished with modern fittings, including a cleverly fitted kitchenette. This picturesque cottage is located in the quiet, rural setting of Shitterton, in the village of Bere Regis, Dorset. We are within easy reach of Dorset's many attractions.

Top guest favourite

Tiny home in Tincleton

4.99 out of 5 average rating, 158 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!

Superhost

Guest house in Bere Regis

4.81 out of 5 average rating, 129 reviews

Unique Private Cabin in Purbeck Dorset Countryside

The Cabin offers a relaxing and private get away in West Dorset close to the Jurassic Coast. The Cabin is perfect for 2 adults with flexibility for a small cot & dogs are welcome. It has a private garden space overlooking nearby woodland. There is an open plan living & sleeping space with double doors opening onto the decking creating an inside out feel. The location offers easy access to neary towns and coastal spots: Studland, Corfe, Wareham, Dorchester, Lulworth, Swange, Weymouth.

Guest favourite

Treehouse in Dewlish

4.93 out of 5 average rating, 311 reviews

Tree-Tops Treehouse Eco Retreat

This beautifully crafted treehouse is deceptively spacious and is set elevated into the tree canopy with woodland to three sides affording total privacy. Facing due South, it commands extensive views over the Upper Piddle Valley in an Area of Outstanding Natural Beauty. With so much privacy, many guests opt to “stay put” but, if you want to venture further afield there are famous landmarks like Durdle Door, Lulworth Cove, Weymouth, and the Jurassic Coastline all within a short drive away.

Top guest favourite

Apartment in Hilton, Blandford Forum

4.97 out of 5 average rating, 145 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 a 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.

Guest favourite

Cottage in Lewell

4.94 out of 5 average rating, 282 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.

Top guest favourite

Shepherd’s hut in Dorchester

4.95 out of 5 average rating, 139 reviews

Troytown Farm Bespoke Shepherd's Hut

A bespoke shepherd's hut, made by a local craftsman residing on rolling pasture of a forgotten turf maze and meeting place lost in time. Welcome to the first Troytown shepherd's hut, completed in June 2023. Located on Dorset's famous Jurassic Coastline it is the perfect base for exploring sandy beaches, historic monuments and plentiful walks in nearby Puddletown Forest. Enjoy an off grid experience with views of ancient woodland and sheep grazed pasture.

Guest favourite

Cottage in Milborne Saint Andrew

4.9 out of 5 average rating, 346 reviews

Manor Farm Cottage

Welcome to Manor Farm air b n b. Self catering cottage on our sheep and arable farm in rural Dorset. Sleeping up to 5 guests - discover the beauty of Dorset in an idyllic location. The cottage sits on one of the highest points on our working farm, in a field called the nursery. Enjoy spectacular unspoilt scenery in peace and tranquillity. The perfect spot for a rural retreat that's close to all of Dorset's wonderful attractions.