Holiday rentals in Shaftesbury

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Top-rated holiday rentals in Shaftesbury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The open-plan living area features a soft carpet and neutral walls, with a comfortable armchair and simple side table. A modern kitchen is visible in the background, equipped with essential appliances. Decorative plants add a touch of warmth to the space.
Guest suite in Shaftesbury
4.98 out of 5 average rating, 251 reviews

Spacious, private annexe with garden, Shaftesbury.

Private and spacious annexe in Shaftesbury, with it’s own entrance Double bedroom with en-suite, walk in shower. Single fold away bed, cot and toddler bed available for younger guests. Well equipped kitchen - fridge freezer, hob, oven, microwave, coffee machine, washer dryer. Open plan living and dining area, Sky TNT Sports TV Private garden with table and chairs. Key safe entry system. Off road parking. 10 min walk from central Shaftesbury and Gold Hill. Close to Longleat, Stourhead, and more

Top guest favourite
Cottage in Shaftesbury
4.99 out of 5 average rating, 196 reviews

Little Coombe

Little Coombe welcomes all couples, lone travellers and fellow pooches. Little Coombe is a totally self-contained cottage attached to the main cottage, where the owner lives. It is a tranquil stone cottage sitting by the brook in a small hamlet near Shaftesbury. The cottage was formerly two thatched farm cottages and where our family has lived for nearly 100 years! We live next door in the main cottage, but guests will have their own entrance and garden space and their privacy is guaranteed.

Top guest favourite
The entrance to the studio apartment is framed by vibrant purple wisteria cascading over a decorative gate. The exterior is clad in light-colored paneling, complemented by potted plants placed symmetrically at the entrance. Gravel pathways provide access to the front door.
Guest house in Cann Common
4.98 out of 5 average rating, 138 reviews

Self-contained studio

Cute but spacious studio apartment on the edge of Cranborne Chase AONB; only 5 mins drive to the historic town of Shaftesbury. 'Bumbles' is the perfect place to provide easy access to a wealth of attractions, whether it be the newly re-opened Compton Airfield, famous Gold Hill and Shaftesbury Abbey, Breezy Ridge Vineyard, Stonehenge or even a day out at the beach! Guests are also offered discount on treatments at the onsite beauty studio, and are welcome to relax in the adjoining orchard.

Top guest favourite
An iron gate, labeled 'Pump Yard,' opens into a landscaped area surrounded by stone cottages. Lush greenery and flowering plants frame the entrance, leading to a gravel path that connects the cottages in a serene courtyard.
Cottage in Shaftesbury
4.97 out of 5 average rating, 111 reviews

Cosy 1-bedroom cottage in Dorset

Welcome to peace and relaxation in my Grade II listed cottage in historic Shaftesbury. The self-catering cottage is in a unique gated courtyard near the foot of Gold Hill and is within a short walk of the town centre and a local pub. It is compact and therefore suitable for singles and couples (I do not accept 3rd party bookings), and we also welcome well-behaved pets. You will have use of a private enclosed garden a short walk from the cottage, and on-street parking is available nearby.

Top guest favourite
The exterior of a rustic barn features a stone façade with wooden elements. Large, sliding glass doors are framed by weathered wood. A small window with flower boxes is visible to the left, and a traditional wooden door borders the entrance, adding character to the setting.
Place to stay in Cann Common
4.97 out of 5 average rating, 276 reviews

The Barn - peaceful country setting.

A converted barn at Cann Common next to the main house with its own garden, patio and parking area. Located on a no-through road with only local residents traffic, giving a peaceful setting with views of the surrounding hills. Shaftesbury just over a mile with its historic Gold Hill and a good choice of shops and places to eat. It is a good base for exploring the area, offering historic houses, interesting gardens, walks, the Jurassic Coast, Stonehenge, Salisbury and Bath and much more.

Top guest favourite
Cottage in Shaftesbury
5 out of 5 average rating, 33 reviews

Button Cottage on Gold Hill Breath-taking Views

A rare chance to stay on the ancient cobbles of Gold Hill, England’s most iconic street and home of the famous Hovis Bread advert. Button Cottage is a Grade II listed, 450-year-old former button makers’ home, built from ancient Shaftesbury Abbey stone and restored to an authentic, 5 star standard. With sweeping countryside views and walks, a secluded courtyard garden and artisan shops, cafés and welcoming pubs just a stroll away, it’s a beautifully romantic and enchanting couples retreat.

Top guest favourite
A charming wooden structure is set against a backdrop of rolling hills shrouded in soft morning mist. Lush greenery and wildflowers surround the building, creating a serene atmosphere typical of the Dorset countryside.
Tiny home in Shaftesbury
4.98 out of 5 average rating, 240 reviews

The Apex: a tiny house retreat in a wild meadow

A wonderful and unique tiny house on wheels, The Apex is nestled within a wildlife habitat surrounded by unspoilt views of the rolling Dorset countryside. Stay and experience the ideal retreat in which to relax and unwind, from where you can venture out on country walks in nature and to neighbouring rural villages and towns. Enjoy the loft-style bedroom and separate reading room floating above a fully equipped kitchen and living area, looking out to an area of outstanding natural beauty.

Top guest favourite
A charming exterior of the cottage is surrounded by lush greenery and colorful flower beds. Two large windows brighten the front, while a white door invites entry. A wooden bench offers a serene spot for relaxation in the garden, complemented by various shrubs and plants.
Cottage in Shaftesbury
4.93 out of 5 average rating, 139 reviews

Charming Grade II listed cottage in Shaftesbury

A charming Grade II listed cottage, just a 10 minute walk from the centre of Shaftesbury with easy access to countryside and coast. Comfortable accommodation for up to 8 guests with off street parking. The cottage comprises of fully fitted kitchen, dining room and sitting room both with wood burning stoves, ground floor family bathroom, upstairs cloakroom and four bedrooms over two floors. There is a pretty garden to the front of the property with two seating areas.

Guest favourite
A row of quaint cottages is visible on a gently sloping hill. The buildings feature a mix of textured stone and brick exteriors, with sloping roofs and chimney pots. Lush greenery surrounds the cottages, adding to the serene setting against a softly lit background.
Home in Shaftesbury
4.99 out of 5 average rating, 71 reviews

Stay right on Gold Hill (famous Hovis ad)

A special opportunity, unlike anything else, to stay right on Gold Hill in a luxury one bedroom cottage that has been immaculately restored. Gold Hill is known for the famous 'Hovis bread' ad and many visitors come to Shaftesbury in Dorset and photograph the spectacular views from the hill. With no passing traffic, the cottage is very quiet and peaceful, yet you are only steps away from the shops, restaurants and pubs in the High Street.

Top guest favourite
A view of charming cottage homes with thatched roofs is captured, set against a backdrop of lush green hills. The picturesque countryside leads down to a stone pathway, bordered by a wooden fence that complements the natural landscape.
Home in Shaftesbury
5 out of 5 average rating, 25 reviews

"Hovis Hill" Cottage, Gold Hill, Shaftesbury.

Our cottage is the last one on the famous Gold Hill in Shaftesbury, Dorset (at the bottom). The hill that was made famous by the Hovis bread advertisement, directed by Ridley Scott. The first flight of stairs is extra steep so please consider this if you have small children or might find this challenging. There is no TV in the cottage so please consider bringing alternative entertainment if you are planning to spend quiet evenings in.

Superhost
A compact kitchen area features a wooden countertop, a sink, and a stove, complemented by patterned tiles. A wood-burning stove is positioned nearby, contributing to a comfortable atmosphere. Natural light enters through a window adorned with floral curtains, enhancing the inviting interior.
Shepherd’s hut in Shaftesbury
4.81 out of 5 average rating, 90 reviews

Lovely Shepherds Hut with stunning views.

Holyrood Shepherds Hut is situated in a 100 acre working farm, in a peaceful spot, 5 minutes walk to the famous Gold Hill and the centre of Shaftesbury, which has a variety of independent shops, coffee shops, pubs and restaurants. There are many attractions close by and the beautiful Dorset coast is only 45 minutes drive. Brilliant for a weekend break or for longer if you are keen to explore what Dorset and Wiltshire have to offer.

Guest favourite
Cabin in Dorset
4.88 out of 5 average rating, 170 reviews

The Boat House, Shaftesbury

A beautiful 2 bedroom wooden cabin set on a working farm, a short walk from the picturesque village of Shaftesbury, Dorsett. The Boat House is set in acres of rolling Dorset countryside looking out onto one of the number of lakes on the farm. The Boat house is dog friendly and sleeps up to 4 adults and 2 children. Relax with the whole family at this peaceful place to stay.

Popular amenities for Shaftesbury holiday rentals

When is the best time to visit Shaftesbury?

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Avg. price$180 SGD$195 SGD$185 SGD$188 SGD$198 SGD$207 SGD$205 SGD$214 SGD$204 SGD$200 SGD$178 SGD$198 SGD
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Frequently Asked Questions

  • What are the best places to stay in Shaftesbury?

    Shaftesbury has options around the town centre for those interested in historic architecture and proximity to markets, cafes, and local landmarks. The surrounding countryside features stays in converted barns, cottages, and farmhouses.

  • What are the best things to do in Shaftesbury with kids?

    Families can explore Shaftesbury Abbey Museum, visit local parks for outdoor games, or follow nature trails in the nearby countryside. Gold Hill often attracts children curious about history and the classic hilltop views.

  • What are some of the best things to do in Shaftesbury?

    Explore Shaftesbury’s historic streets, stroll Gold Hill, and visit Shaftesbury Abbey Museum for insight into the area’s monastic past. The town also has art galleries, independent shops, and peaceful green spaces.

  • How is the weather in Shaftesbury?

    Shaftesbury has cool winters around 36–48°F (2–9°C) and milder summers with highs near 71°F (22°C). Rain falls throughout the year, so a light waterproof layer is practical whenever you visit.

  • When is the best time to visit Shaftesbury?

    Late spring and summer are often recommended for milder temperatures, blooming flowers, and outdoor events. Autumn brings colorful foliage to the surrounding countryside, while winter has quiet streets and festive markets.

  • What are the best places to visit in Shaftesbury?

    Popular sites include Gold Hill for its iconic slope, Shaftesbury Abbey Museum with gardens, and local art galleries. The town’s market square is also known for seasonal events and independent shopping.

  • What are some hiking trails in Shaftesbury?

    Shaftesbury has scenic walking paths, including the Gold Hill trail, which is known for its historic cobblestone slope and countryside views. Around the town, explore local footpaths weaving through green hills, woodlands, and farmland.

  • What are some family activities we can do in Shaftesbury?

    Families can tour the Shaftesbury Abbey Museum, enjoy picnics in nearby parks, or hunt for snowdrops in the local garden during early spring. Exploring Gold Hill has wide appeal for its history and views.

  • What are some of the best day trip ideas from Shaftesbury?

    Explore nearby historic towns, ancient stone circles, or walks in the rolling hills of the Cranborne Chase Area of Outstanding Natural Beauty. Local farms and rural villages provide a glimpse into Dorset’s agricultural life.

  • Are there any pet friendly accommodations available in Shaftesbury?

    Many Shaftesbury stays welcome pets, especially in the surrounding countryside where walking trails and green spaces are abundant. Some town centre rentals also accommodate guests with dogs.

  • What are some local tips for visiting Shaftesbury?

    Visit Gold Hill early or late in the day for quieter moments, and check local listings for market days or pop-up events. Comfortable footwear is useful, as some streets are cobbled and steep.

  • What is Shaftesbury known for?

    Shaftesbury is known for its steep Gold Hill, often featured in British film and television, and its Saxon roots. The town has a preserved abbey site, traditional markets, and panoramic countryside views.

  • What are the best foods to try in Shaftesbury?

    Shaftesbury has locally baked breads, Dorset Blue Vinny cheese, and hearty pies often found in traditional pubs or markets. Afternoon tea with scones and regional preserves is frequently suggested for visitors.

  • What should I bring for a trip to Shaftesbury?

    Bring comfortable shoes for exploring steep streets, a waterproof jacket due to frequent showers, and layers for cooler evenings. A reusable bag is helpful for market shopping and local produce.

  • What is the nightlife in Shaftesbury like?

    Nightlife in Shaftesbury is relaxed, with welcoming pubs, microbreweries, and venues hosting live music or quiz nights. Some local restaurants host themed evenings or culinary nights.

  • What are the most popular events or festivals in Shaftesbury?

    Shaftesbury frequently hosts an annual Food and Drink Festival showcasing local produce, as well as spring snowdrop celebrations in the Snowdrop Garden. Seasonal markets, craft fairs, and outdoor performances occur throughout the year.

  • Are there family friendly vacation rentals in Shaftesbury?

    You can find family-friendly rentals in and around Shaftesbury, including spacious cottages, converted barns, or town centre homes. Many have outdoor areas and flexible layouts to suit a range of travelers.

  • How much does it cost to stay in cottage rentals in Shaftesbury?

    Experience the best of Shaftesbury with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about holiday rentals in Shaftesbury

  • Total holiday rentals

    Explore 50 holiday rentals in Shaftesbury

  • Nightly prices starting at

    Shaftesbury holiday rentals start at $78 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,910 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Shaftesbury holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shaftesbury rentals

  • 4.9 Average rating

    Shaftesbury stays are highly rated by guests – averaging 4.9 out of 5!

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