Shepherd Oak

Upwey, near Weymouth, Dorset
4 Guests
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    Shepherd Oak, sleeping 4, is an architect-designed semi-detached cottage
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    Shepherd Oak, constructed and furnished to a very high standard, has vaulted ceilings and floor-to-ceiling windows
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    Ground floor: Sitting & dining area in the open plan living space, with floor-to-ceiling windows
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    Ground floor: Open plan living space comprising kitchen, dining and sitting areas
  • View Large
    Ground floor: Kitchen area in the open plan living space
  • View Large
    Ground floor: Sitting & dining area in the open plan living space, with floor-to-ceiling windows
  • View Large
    Ground floor: Kitchen area in the open plan living space
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    Ground floor: Double bedroom with zip and link beds which can convert to twin beds on request
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    Ground floor: Bathroom with shower over the bath
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    Mezzanine level: Double bedroom with en suite shower room
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    Shepherd Oak is one of five architect-designed cottages grouped around a courtyard
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    Mezzanine level: En suite shower room to double bedroom
  • View Large
    Mezzanine level: En suite shower room to double bedroom
sleeps4Ground Floor BedroomTwo Nightschildren-01dogwifienclosedGardenparkingAvailablepubeasyWalkingAccessBeach Nearby
Shepherd Oak is an architect-designed semi-detached cottage, one of five on-site grouped around an attractive shingled courtyard. Nestling in a semi-rural south Dorset location, within the valley of the River Wey, on the edge of the village of Upwey, the cottage is just 3.5 miles north of Weymouth. This luxury holiday base is ideal for couples, families or friends who wish to enjoy all that Dorset has to offer.

This quality cottage has been constructed and furnished to a very high standard. Once inside this luxury cottage you will find vaulted ceilings in the open plan living area, along with floor-to-ceiling windows. Also on the ground floor is a king-size double bedroom with zip and link bed and a bathroom, and on the first floor is a mezzanine bedroom with en suite facilities. Open the doors out onto the private patio with outdoor furniture, where you can relax with a glass of your favourite tipple. There’s off road parking for one car, as well as use of attractive shared raised lawned areas that take you up shingle paths to a seating area with picnic benches.

Guests can enjoy the delights of this lovely location, situated close to the family-friendly seaside resort of Weymouth with its golden sands, attractive harbour offering diving and fishing trips and all kinds of watersports.

Locally, take a visit to nearby Portland with its rugged scenery and dramatic Chesil Beach, or venture inland to the attractive bustling market town of Dorchester, Thomas Hardy’s ‘Casterbridge’, where you will find a fine selection of shops and restaurants.

Alternatively, visit historic Sherborne and Shaftesbury and enjoy the footpaths, country lanes and thatched-roof pubs Dorset offers.

In fact there’s so much to see and do, a week is hardly long enough! Shepherd Oak provides an excellent and convenient base from which to explore this stunning coastal area.



  • 4 Guests
  • Two bedrooms; one double, one double/twin
  • One bathroom, one en suite shower room
  • Suitable for a baby (travel cot and highchair on request)
  • Children are welcome
  • The cottage welcomes one well-behaved dog*
  • Private patio with outdoor furniture
  • Shared hillside garden with picnic benches
  • Bed linen and towels included
  • Parking for one car


  • One of a cluster of five impressive cottages nestling in a semi-rural south Dorset location.
  • Architect-designed, with floor-to-ceiling windows, and vaulted ceilings.
  • Designed with your comfort and relaxation in mind and tastefully furnished, with a sociable open plan living area.
  • Private large patio sitting area and shared use of an attractive hillside garden with picnic benches.
  • Flexible accommodation with one ground floor bedroom and one bedroom which can be either a twin or double to suit your party.
  • The perfect base for couples, families or friends who wish to enjoy all that Dorset has to offer.
  • Short and mid week breaks are available, with a minimum stay of two nights.
  • Brilliant in all seasons and the ideal setting for Autumn and Winter breaks.
  • Just 3.5 miles from the family-friendly seaside resort of Weymouth with its golden sands and attractive harbour offering all kinds of watersports.
  • The market town of Dorchester, Thomas Hardy’s ’Casterbridge’ is just a short drive.
  • Explore the fossils and stunning beaches of Dorset’s Jurassic Coast, visit historic Sherborne and Shaftesbury, or enjoy the footpaths, country lanes and thatched-roof pubs Dorset offers.
  • There is a shop and pub only 10 minutes’ walk away.

Property layout

  • Ground floor

    Open plan living space, with floor-to-ceiling windows, comprising kitchen, dining and sitting areas.

    Double bedroom with a 5′ zip and link bed which can convert to twin beds on request.

    Bathroom with shower over the bath.

  • Mezzanine

    Double bedroom with en suite shower room.


  • Gas central heating
  • Electric oven and ceramic hob, microwave, fridge, dishwasher, washer/dryer.
  • 3 x Smart TVs with Freeview
  • WiFi internet access*
  • Outdoor furniture
  • Off road parking for one car


”Had a great stay at Shepherd Oak, it was a really good base to explore Dorset. The cottage is excellent and the owner was really helpful from start to finish. Would highly recommend to anyone looking for a pet friendly location.”
Mr Steve Parker, Sutton Coldfield, West Midlands – April 2016

There really is an exhaustive selection of places to go and things to do during your stay at Shepherd Oak – here’s just a snapshot of some ideas to inspire you…


The picturesque village of Upwey lies just four miles north of Weymouth, nestling beneath the Dorset Ridgeway, and takes its name from the shallow chalk stream which bubbles up from an underground spring. Upwey is well-known for its Wishing Well, where George III once sought the benefits of the natural spring water, but is now a delightful tea room serving traditional cream teas.

An easy drive or bus ride takes you to the popular seaside resort of Weymouth offering visitors glorious golden sandy beaches, excellent watersports facilities and a bustling harbour, whilst the market town of Dorchester, Thomas Hardy’s ’Casterbridge’ is also just a short drive or bus ride away. Walkers to Upwey can easily travel by train and bus to the Wishing Well.

An attractive village location and an ideal place to escape from the hustle and bustle of everyday life.


WEYMOUTH (3.5 miles). Top attractions include the SEA LIFE Adventure Park & Tower, Brewer’s Quay, fishing and the great family beach, the winner of a seaside award.

DORCHESTER (4.5 miles), Hardy’s ‘Mayor of Casterbridge’ has many fascinating museums including the Tutankhamun Exhibition, The Dinosaur Museum, the Dorset County Museum, the Teddy Bear Museum and the Terracotta Warriors Museum. Other attractions include Max Gate, Thomas Hardy’s Home (National Trust), the Roman Town House and Maumbury Rings.
Nearby Maiden Castle (English Heritage) is largest hill fort in England.

ABBOTSBURY (7 miles) is home to the lovely Abbotsbury Subtropical Gardens, Abbotsbury Swannery and Children’s Farm.

PORTLAND (8.5 miles), five miles south of Weymouth, great for fishing, sailing and rock climbing. Attractions include Portland Castle (English Heritage) and Portland Museum.

CERNE ABBAS (13 miles) is a charming and quaint village that is world renowned for the Cerne Giant (National Trust), a 180 ft high ancient chalk figure carved out into the steep sloping hillside above the village. There is an extensive range of public footpaths and bridleways throughout the village and walks to suit every taste. Other attractions include the Cerne Abbey remains and the Medieval Tithe Barn. Visitors can enjoy food and drink in some picturesque surroundings in pubs such as The New Inn, The Giant Inn and The Royal Oak and Abbotts Tea Rooms.

BURTON BRADSTOCK (14 miles) is a pretty village with lovely Hive Beach, the Hive Beach Cafe, a shop and pubs.

BRIDPORT (16 miles) is an elegant town with antique markets (on the Sunday of each month), farmer’s markets, unusual and specialist shops and supermarkets, historic Georgian buildings and a wide range of outstanding restaurants and pubs. At the twice weekly market, local produce can be sampled as featured in the popular ‘River Cottage’ TV series. Attractions include Palmers Brewery Tours and the Bridport Arts Centre.

WEST BAY (16.5 miles) is the dramatic Jurassic coastal setting for TV’s Broadchurch, with its bustling harbour and scenic coastal walks. Boating and sea fishing trips can be arranged at the picturesque harbour.

CORFE CASTLE village (22 miles) offers a unique range of independent shops, pubs, restaurants, teahouses and two free museums and is best known for its Castle, Corfe Castle (National Trust).

SHERBORNE (24 miles) is a beautiful, small market town which boasts a wealth of unspoilt medieval buildings, the splendid Abbey Church, Sherborne Castle & Gardens and the ruins of Sherborne Old Castle.


Bennetts Water Gardens, Putton Lane, Chickerell, Weymouth (3.7 miles).

Kingston Maurward Gardens & Animal Park, Dorchester (6.7 miles).

Abbotsbury Subtropical Gardens, Abbotsbury (7 miles).

Hardy’s Cottage (National Trust), Higher Bockhampton, Dorchester (7.7 miles).

Portland Castle (English Heritage), Portland (8.3 miles).

Athelhampton House and Gardens, Athelhampton, Dorchester (11 miles).

Clouds Hill (National Trust), Bovington, near Wareham (13.3 miles), the rural retreat of T. E. Lawrence.

Minterne House & Gardens, Dorchester (14.7 miles).

Lulworth Castle & Park, The Lulworth Estate, East Lulworth (17.5 miles).

Corfe Castle (National Trust) (22 miles).

Mapperton House & Gardens, Beaminster (22 miles).

Montacute House (National Trust), Montacute, Yeovil (29.6 miles).


Abbotsbury Swannery and Children’s Farm, Abbotsbury (7.7 miles).

Isle of Purbeck, which in fact is a peninsula, is a World Heritage Site fringed with unspoilt beaches including Studland Bay and Lulworth Cove, West Lulworth (14.8 miles) with its spectacular scenery. There is a fine cliff top walk to Durdle Door, West Lulworth (14 miles), a Natural Chalk Arch. Swanage is the main town in the area.

Monkey World, Longthorns, Wareham (14.7 miles).

The Tank Museum, Linsay Road, Bovington (15 miles).

Henley Hillbillies (Quad Bikes etc.), Old Henley Farm, Buckland Newton (15.7 miles). Based on the 180 acre family farm, all the activities are on site. Quad bikes, mini mavericks, clay pigeon shooting, hovercraft flying, archery and crossbow and air rifle shooting.

Mangerton Mill, Mangerton, Bridport (18 miles).

Furleigh Estate Vineyard and Winery, Furleigh Farm, Salwayash (19.7 miles) – Vineyard Tours.

The Blue Pool & Tea House near Wareham (21 miles).

Farmer Palmer’s Farm Park, Wareham Road, Organford, Poole (22 miles) for children around 8 and under. There are animals to look at, touch and feed, play areas, a straw mountain, outside animal pens, bouncy castle, tractor trailer rides, woodland walk, cafe and shop.

UK Llamas, New House Farm, Beaminster (24.5 miles) offers trekking around the county with Llamas.


Came Down Golf Club (5.3 miles) is a 12 minute drive.
Weymouth Golf Club (3.3 miles) is a 10 minute drive.



Visitors’ Notes

Things you need to know about Shepherd Oak if you’re thinking of booking a holiday there:

  • Smoking is not allowed inside any of our properties
  • *This cottage welcomes one well-behaved dog. Your pet must be kept on a lead whilst outside, and nearby kennels are available to rent by arrangement with owner.
  • There is a sloping ceiling in first floor bedroom.
  • Minimum stay 2 nights in off peak periods. Minimum stay 7 nights Friday to Friday during Summer High season.

*Internet access is offered at this property for recreational purposes only and is not meant for business use. Speed/service may vary depending on the package obtained by the owner which is provided to guests free of charge. Should guests experience difficulties or loss of use, neither the owner nor the agent will be held responsible.