Vacation rentals in Tolpuddle

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Top-rated vacation rentals in Tolpuddle

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Guest favorite
A charming wooden cabin features a rustic design with blue trim around the windows and door. The surrounding garden includes young plants and a patio area showcasing seating and a BBQ grill. Trees provide a natural backdrop, highlighting the peaceful rural setting.
Cabin in Affpuddle
4.89 out of 5 average rating, 47 reviews

Piddle Puddle Cabin

Imagine yourself in the grounds of a 16th Century thatched cottage, in rural Dorset. The river Piddle can be heard flowing nearby and the birdsong and gentle breeze is whispering through the trees. You are surrounded by fields, heathland and forests, and the Jurassic Coast is just a few miles away. Heaven... well that's what we think anyway, and we would like to share it with you. Come to stay in our beautiful log cabin, complete with spacious raised deck with views down to the river Piddle.

Top guest favorite
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, 142 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 favorite
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, 292 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.

Guest favorite
Home in Milborne Saint Andrew
5 out of 5 average rating, 28 reviews

Woodland View, 2 Greenacres Bungalows

Welcome to Woodland View- 2 Greenacres Bungalows a stylish two bedroom countryside retreat in Dorset, sleeping up to four guests. This light filled home features open plan living, a modern fully equipped kitchen, cosy lounge with wood-burning fire. The property offers a king size bedroom, a double bedroom and a sleek bathroom with bath and separate shower. 510 sq ft. Outside, enjoy a large private garden, patio with barbecue and a luxurious hot tub. Secure parking, Wi-Fi, Smart TV and Alexa.

Top guest favorite
An outdoor table is set with two wine glasses, a bottle of sparkling wine, and decorative plates. A vibrant candle stands in a holder, while a floral arrangement adds a touch of nature. The backdrop features a sunset casting warm colors over the landscape.
Tiny home in Puddletown
5 out of 5 average rating, 110 reviews

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.

Top guest favorite
A quaint cob cottage with a thatched roof is framed by vibrant pink flowers and lush greenery. The garden features well-maintained plants and an inviting path leading to the cottage's window, creating a serene and welcoming outdoor space.
Tiny home in Bere Regis
4.96 out of 5 average rating, 234 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 an 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 favorite
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 Tincleton
5 out of 5 average rating, 206 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!

Guest favorite
The exterior of a charming one-bedroom annex is shown, featuring a blend of white and stone walls with a sloping roof. A private patio area with outdoor seating is visible, along with surrounding trees and clear blue skies, suggesting a serene countryside setting.
Home in Briantspuddle
4.84 out of 5 average rating, 122 reviews

Historic one bedroom annex in secluded Dorset

Break away from the rush, in this secluded, beautifully presented one bedroom annex in the idyllic Dorset countryside with close proximity to the sea at Weymouth and Poole, award winning Dorset Golf resort, and the county towns of Dorchester and Blandford. Enjoy quiet walks from the doorstep, based in a historic home once owned by Sir Ernest Debenham. Blending historic architecture with 21st Century technology and high speed broadband, this meets the needs of most discernible visitors!

Top guest favorite
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 Tincleton
5 out of 5 average rating, 92 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.

Top guest favorite
Cottage in Milton Abbas
5 out of 5 average rating, 22 reviews

Luxury Cottage | Sleeps 8 | Jurassic Coast

Luxury 4-bedroom cottage in Milton Abbas, Dorset, sleeping up to 8 guests, with parking, fireplaces and stylish interiors — just 25 minutes from the Jurassic Coast and Lulworth Cove. St James Cottage is a beautifully restored Grade II listed home blending timeless charm with modern comfort. Recently refurbished to an exceptional standard, it features three elegant living areas, a high-end kitchen and inviting fireplaces, creating the perfect countryside escape for families and groups.

Top guest favorite
A charming barn-style building with a rustic wooden exterior is featured, complemented by solar panels on the roof. A fenced area is visible in the foreground, with outdoor seating arrangements and potted plants enhancing the entrance.
Home in Tolpuddle
4.98 out of 5 average rating, 84 reviews

Park Farm Byre

Relax in the heart of the Dorset countryside. Located 1 mile from the historic village of Tolpuddle, in a rural location, Park Farm Byre sleeps 5 guests in 3 bedrooms. The Byre has an open plan kitchen-dining-living room, and a log burning stove. Outside there is a courtyard area with bbq, outdoor dining table and a wood fired hot tub. The friendly owners are on site but you are assured of your privacy. Dorchester is 15 minutes away, and it’s 25 minutes to the stunning Jurassic Coast.

Guest favorite
A private terrace features a wooden table and two folding chairs, set for a relaxing moment. Two wine glasses are positioned on the table, with a backdrop of lush greenery and a clear blue sky, inviting peaceful outdoor enjoyment.
Loft in Piddlehinton
4.88 out of 5 average rating, 134 reviews

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.

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