Family-friendly holiday rentals in Puddletown

Large 2 bedroom town centre flat with free parking

Located overlooking Dorchester’s beautiful, tranquil Borough Gardens, this very spacious two bedroom flat provides the perfect place to enjoy a break in splendid Dorset’s historic county town. The property is only a two minute walk from the main high street of the town with its shops, museums and historic buildings. It is also within easy, level walking distance to the two train stations and many bus routes. A free parking space included allows guests to visit all areas of the county with ease.

Kitchen · Family · Location

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.

Kitchen · Indoor spaces · Parking

Large coastal cottage with spa and private pool

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Kitchen · Indoor spaces · Walkability

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.

Family · Kitchen · Laundry

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.

Indoor spaces · Family · Comfort

The Yorkshireman @ Piddlehinton

We are so excited about our conversion. Completely self-contained, it is a lovely, light, cosy open space with a well equipped kitchen, modern bathroom and a cool sleeping platform/mezzanine. Piddlehinton is a special place, 20 mins from the Jurassic Coast and 10 mins from Dorchester, in the renowned Piddle Valley, with beautiful walks, views and our award winning pub, The Thimble Inn. We are right next door if you need anything, but if you prefer your privacy, you can be totally separate.

Family · Kitchen · Parking

Little Piddle

Little Piddle is a charming, self-contained annex set within the garden of our home — the perfect spot to relax in Dorset. Surrounded by nature enjoy views across fields and the water meadows, with the River Piddle flowing through our garden. It’s a haven for wildlife lovers, with plenty of birdlife to watch from your own private balcony. The annex is self-contained, offering privacy and comfort during your stay. Ideal for couples or solo travelers looking to escape the hustle and bustle.

Family · Indoor spaces · Hospitality

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!

Indoor spaces · Family · Amenities

Stunning Barn conversion with heated swimming pool

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

Family · Kitchen · Parks

Retreat studio with a terrace

A beautiful new studio in the Dorset countryside with stunning views, a private entrance and a private terrace to relax on. The studio is equipped with an ensuite bathroom and a new kitchenette for your use only. Located opposite the awards winning pub "Thimble Inn" in a friendly village in the scenic Piddle Valley. It is a perfect central location to explore Dorset, with many attractions nearby, only 10min drive to the Cerne Abbas giant or Dorchester and 25min to the Jurassic Coast.

Indoor spaces · Family · Long stay

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.

Kitchen · Family · Comfort

Troytown Farm Traditional Shepherd’s Hut Cabin

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 cabin experience with views of ancient woodland and sheep grazed pasture.

Family · Kitchen · Outdoor spaces