A Guide to Weymouth & Portland » Dream cottages

A Guide to Weymouth & Portland


About Weymouth

About Portland

Weymouth and Portland during the seasons

Things to do in Weymouth and Portland


Pet Friendly


About Weymouth

For a wonderful English seaside holiday destination, it would be very hard to top Weymouth. We are lucky enough to call this perfect English seaside town, home, and as such we are in the perfect position to tell you all about it!

Weymouth is the perfect place to recapture the nostalgia of childhood family holidays. The beach is golden and sandy and bustling with activity. The fine sand is great for sand castle building and the shallow paddling waters are perfect for families. The traditional Punch and Judy puppet shows, donkey rides, carousels, fish and chip shops, penny slot machines and the best sunshine record in England mean that Weymouth beach is pretty much the best family holiday location on the planet! (We could be biased)

The town itself is beautiful. The beach is positioned against a backdrop of impressive Georgian buildings, dating back some 200 years, when Kind George III famously spent his holidays here. The Royal Hotel, once the Assembly Rooms, was a favourite spot for King George for dancing and socialising. If you look at the Georgian townhouses and villas along the sea front, you will notice that many of them do not have letterboxes, since the penny stamp was not invented until 1840.

One of the most wonderful things about Weymouth is the harbour. Reputed to be one of the prettiest in Europe, it is alive and bustling with crabbers and fishermen and the best place to take a walk with a bag of freshly caught Billy Winters (Weymouth Bay prawns), soaking up traditional harbour life. There are some wonderful pubs and restaurants dotted along the harbour, where fish is served directly from the sea in front.


About Portland

Portland is a part of Dorset that is unlike the rest of the county. While the rest of Dorset is all rolling green hills, golden beaches and idyllic English villages, Portland is beautiful but in a completely different way. Portland, which is a majestic lump of rock rising above the sea, is wild, rugged and dramatic. It is faintly connected to the rest of Dorset by the sweep of Chesil Beach.

The famous red and white Portland Bill Lighthouse is at the southernmost tip of Portland and is a feature on many a Dorset postcard. Paying a visit to the lighthouse should definitely feature on your Portland itinerary. Climb to the top and see for miles across the beautiful Dorset coastline. Gaze down to the most treacherous patch of sea in the area ‘The Portland Race’, which has resulted in the demise of many a ship over the years.

The villages within Portland are completely charming, filled with old stone cottages, cobbled streets, traditional shops and cafes which serve the most delicious cake, cream teas and coffee you will find. The main village in Portland is Easton which sits on the plateau. Then there is Fortuneswell, which lies on a steep hill. Thomas Hardy wrote of Fortuneswell ‘houses above houses, one man’s doorstep rising behind his neighbour’s chimney’ and this is such a perfect way to describe this lovely village.

The geological location of Portland is such that it attracts rare and wonderful birds and wildlife, so take a ramble along the many networks of footpaths and see what you can spot!


Weymouth and Portland during the seasons

Weymouth and Portland in the spring

The Dorset countryside is resplendent in spring. It’s perfectly gorgeous all year round, but after the cold dark wintry days, when the sun peeps out and the flowers spring, it truly is a sight to behold.

Enjoy al fresco lunch or dinner on the warmer spring days in Weymouth’s Hope Square and make the most of the lovely restaurants and pubs. Or head harbour side and sip wine whilst you watch the yachts and fishing boats come and go.

Take a walk on the South West Coastal path around Portland and glimpse the wildlife, which heads here in the springtime. Spring is one of the most exciting times of the year on Portland in terms of the varieties of birds that you will spot, with April at Portland Bill being the time to witness the fascinating scenes of seabird migration.


Weymouth and Portland in the summer

Staying in a seaside holiday cottage during the summer months provides ample opportunities to keep the children entertained. Sandcastles, paddling and picnics can be followed by al fresco dinners right next to the sea.

Waking up to fresh sea air is so invigorating and can really help to press the pause button on stressful, busy lives. There is also nothing like fresh sea air to help the little ones go to bed nicely exhausted at night! This leaves parents to spend their evenings sipping wine, watching movies, or sitting on the terrace or private garden of one of our beautiful self-catering cottages.

For a traditional seaside holiday, there is no other place like Weymouth. The lure of Weymouth’s wide bay, sandy beach and elegant esplanade has been tempting holidaymakers for around 250 years and we love having our Dream Cottages office right here in the heart of it. The beach itself has won numerous awards and even just last month, it was awarded ‘No. 1 Beach in the UK’ by TripAdvisor users. It has even been awarded ‘9th best beach in Europe’!


Weymouth and Portland in the autumn 

An autumn break by the seaside in a cosy cottage is just what we all need, moving towards the end of our year. Autumn is when we want to cosy up, take bracing walks, kick through the autumn leaves and then retire to a cottage with an open fire or wood burning stove, with a warm cup of hot chocolate.

If walking is something that you are keen to do in the autumn months, The Weymouth and Portland Legacy Trail is the most wonderful things to do and one of the best ways to explore Dorset. The whole trail is 20km long, from Littlemoor through to Portland Bill or you can visit the main sites by bicycle, bus or car. The walk takes in all the places on the ‘Wild about Weymouth and Portland’ postcards and there are ten circular walks from each spot. The postcards each feature the wildlife that can be seen from each place, from Barn Owls at Lorton Meadows, Little Tern Birds at Chesil Beach, Kestrels at the Merchants Incline, Starling on the Esplanade and Razorbill on the Portland Bill. Simply take your pick from this fantastic wildlife selection and head to these beautiful Weymouth and Portland areas for your fill of enriching wildlife.


Christmas and New Year in Weymouth and Portland

If you are staying in a Dream Cottage in Weymouth or Portland over the festive period and are looking for New Year’s Eve entertainment, just head to Weymouth town centre! Weymouth embrace the countdown to the new year like nowhere else! The town becomes one huge party with everyone wearing fancy dress, live music in the town and in many of the pubs and a loud rendition of Ault Land Syne around the clock. For more glamorous events, many of Weymouth’s hotels hold beautiful New Year’s Eve dinners, such as the Rembrandt with their champagne filled 5 course meal followed by their own live music.

Christmas in Weymouth is also not to be missed. Twinkling with lights, there are plenty of Christmas events to get you in the spirit. Markets and local boutiques are a fantastic port of call for finding those one of-a-kind gifts!

Another fine Weymouth tradition happens during the Christmas period every year, normally about a week before Christmas, when hundreds of Santa’s chase a Christmas pudding down Weymouth beach. A lovely 5k run to either join or watch from the sides with a nice warming mulled wine!


Things to do in Weymouth and Portland


Weymouth Beach

A blue flag awarded, golden, sandy beach, recently given the ‘No. 1 Beach in the UK’ award by TripAdvisor users.  The waters are safe and shallow, which makes it perfect for paddling and swimming. Weymouth beach offers good old fashioned bucket and spade entertainment, with Punch and Judy shows and donkey rides on offer during the summer months. There are also some fabulous summer firework displays. Three miles of sand just next to the lovely seaside town and old harbour. Dogs aren’t allowed on certain areas of the beach between the 1st May and 30th September but from October 1st, walk to your dog’s delight!


Chesil Cove

Chesil Cove is part of Chesil Beach, a large naturally formed pebble bank, 15 miles long. The cove is a great spot for sea fishing and scuba diving. There are a few restrictions for dogs on Chesil Cove, but plenty of spots where dogs are welcome.


Castles and Forts

Portland Castle

Portland Castle was one of Henry VIII’s finest coastal forts and was built for protection against French and Spanish invasion. Overlooking Portland Harbour, the castle boasts great views of the sea from the gun platforms. Discover the 450 year old history of the castle and find out how it played its part during the First and Second World Wars. Venture through the Tudor kitchen, armoury and gun platforms and then enjoy tea and cake in the Captain’s Tearoom.


Nothe Fort

Nothe Fort is a fantastic place for the family to visit. Walk through all the tunnels and underground passageways from the lowest level, the magazine level which was used to store the gun powder and shells to the middle level, which housed the canons to the top level which the soldiers used as the platform for firing canons. After learning about the history of the fort, relax with a coffee in the Fort View Café. The Nothe also offer some fantastic seasonal events, so be sure to check their events page before your visit.


Natural Beauties

Pulpit Rock

Climb up onto Pulpit Rock and gaze out to sea from this wonderful vantage point. Pulpit Rocks are a stack of rock on the southern tip of Portland, which were left in the 1870’s by quarryman. Despite it not being a natural landform as such, Pulpit Rock has become something of a tourist attraction and is always worth a visit. On a stormy day, the waves crash over the top of the rocks and it is pretty dramatic to watch. Please only climb on the calm sunny days!

Tout Quarry Nature Reserve and Sculpture Park

At the top of Portland, sits an abandoned stone quarry, which has now become a stone sculpture park. Tout Quarry Nature Reserve and Sculpture Park is sat on the clifftop overlooking Chesil Beach and was once one of over 100 quarries on the island, worked by hand. It really is a fascinating and inspiring place to walk around and see some remarkable structures being carved out of stone as you watch.

Visitors are welcome to take a walk around the old quarry, admiring the various stone carvings that have been produced over the years. You can also take a peek at some of Dorset’s local stonemasons working away in an area of the quarry.


Visitor Attractions

The Portland Bill Lighthouse

The Portland Bill Lighthouse is still a working lighthouse to this day, necessary due to the treacherous stretch of water, known as the Portland Race. Visitors can climb up to the top of the Portland Bill Lighthouse and look down at the ‘Portland Race’ and further across the English Channel.

There is now a Visitor Centre at the Portland Bill Lighthouse, which offers plenty to do. In recent years (2015) it has been given a substantial grant which has allowed it to feature some fun informative maritime displays. Learn about the lighthouse and its keepers and encounter a stormy sea journey in the interactive feature zone ‘Into the Dark.’

After your walk around The Portland Bill, or your venture up to the top of the Portland Bill Lighthouse, you most definitely need to pop in to Portland Bill’s Café; The Lobster Pot Restaurant, famous for its fresh crab and Dorset Cream Teas.


Weymouth Museum

The Weymouth Museum is on the first floor of the beautiful Brewers Quay. Learn everything about Weymouth from the geology and pre-historic times, through to the Romans, Saxons and Danes, the Tudors and then the Georges, Victorians and finally Twentieth Century Weymouth. A nice little gem which costs just one pound to enter!


Sea Life Adventure Park and Tower

Visit the Weymouth Sea Life Adventure Park and experience a fantastic adventure above and below the ocean. With over 1000 fascinating creatures to observe, an underground sea world, attractions and rides, it makes for a fantastic and adrenaline fuelled day out!

The Jurassic Skyline is a viewing capsule, 53m above ground with panoramic views across the Jurassic Coastline and Dorset countryside.





Walk the South West Coastal Path around the Isle of Portland

There is actually a walk right around the Isle of Portland, called ‘The Isle of Portland Circuit’ which follows the South West Coastal Path right around the island. This is 13 miles long, but you needn’t do all of it. Take the dog and follow the dramatic, rugged cliffs, taking in the rare wildlife, hidden coves and stunning views at every turn.

If you are coming from Weymouth, follow the road and cycle way from Ferry Bridge or Chesil Beach, to join the South West Coastal Path as it climbs to the top of the cliff and then away you go!


Bird Watching

Rare Bird Watching at The Portland Bill

Portland is a major migrating point for birds and bird watching enthusiasts have always flocked here, to glance at some rare specimens. There is even a Portland Bill Observatory running from the Lower Old Lighthouse, open from March to November, where everyone is welcome to join and relax, to wait for some glorious glimpses.

The area of Southwell is a happy hunting ground for the local Barn Owls, and it wouldn’t be a surprise to see Little Egrets, Grey Herons, Red-throated Divers and Kingfishers around Portland, to name a few!



Portland and Weymouth Sailing

Well known for the fantastic sailing conditions, owing to the sheltered location, Portland Harbour and Weymouth were a natural choice to host the Sailing Events in the Olympic Games in 2012. In fact, Weymouth Bay and Portland Harbour are reputed to offer some of the best sailing waters on the planet!

Why not try your hand at sailing around Portland? Try a ‘Taster Session’ to begin with by taking a course with The Weymouth Outdoor Education Centre Sailing Courses or if you have already had a taste, why not take a two or four day sailing course!



Fishing from Portland Marina or Weymouth Harbour

There are several Fishing Boat Trips operating from Portland Marina and Weymouth Harbour. They take you fishing at wrecks (of which there are many, as a result of the treacherous ‘Portland Race’) or on the reef or the bank.

You can even go on a ‘Predator Trip’ and look for Porbeagle, Mako and Thresher sharks, all of which have been spotted in the waters off Portland. You can catch the shark but then they are tagged and released. Or how about a ‘Night Time Fishing Trip’.



The beautiful countryside and coastal paths in Dorset are enough to inspire anyone to pack their running shoes and head out on the South West Coastal Path.

If you are a budding runner and are renting one of our wonderful self-catering cottages, why not plan your runs before you go so that you can really experience all the delightful terrains that Dorset has to offer.

There are some really lovely running routes, which will take you through peaceful rural villages, across bracing cliff tops and along golden sandy beaches.

Even if you don’t follow a set route, simply pick up the South West Coastal Path which runs all across the coast, and run for any distance you like. Begin at Weymouth and follow the Ironman route all along the seafront and The Esplanade or head over to Portland along the Portland Beach Road, across Chesil Beach. Wherever you run you can find terrain as challenging, or as gentle as you fancy. Then head back to your cottage and sit by the open fire with a cup of tea and a good book! Enjoy!


Pet Friendly Weymouth and Portland

Pet Friendly Beaches

Weymouth and Portland are absolutely perfect for holidays with your pet. With miles of stunning coastal walks along the heritage status Jurassic coast, pet friendly beaches, welcoming village pubs with beer gardens and country walks right on your doorstep, your four legged friends will enjoy their holiday just as much as you!

Dogs are welcome all year around to Church Ope Cove in Portland and Bowleaze Cove in Weymouth. They are welcome for some parts of the year on Chesil Cove, Weymouth Beach, Castle Cove, Sandsfoot Castle, Greenhill, Preston and Overcombe. The restrictions are generally held between the 1st May and the 30th September each year.


Pet Friendly Pubs and Restaurants

Many pubs and restaurants in Weymouth and Portland lovingly welcome the four legged furry members of your family. After long dog walks, what could be better than to let them curl up beside a cosy open fire which many of our Dorset pubs proudly boast. Here are just some of our favourite pet friendly pubs and restaurants in Weymouth and Portland.

Nothe Fort Café, Weymouth

Nothe Fort is a fantastic dog welcoming attraction in Weymouth. As long as they are kept on a lead, they are permitted to walk around all sections of the Fort with you and are more than welcome in the café for refreshments. Enjoy delicious homemade cakes and cups of tea and take in the view of the Fort with your hairy companion.

The Crow’s Nest in the Square, Weymouth

This gorgeous bistro, sat behind the Old Harbour in Weymouth’s Hope Square is the perfect way to while away the afternoon sipping your favourite tipple and eating delicious food. Tapas is served from 6:30pm every evening and dogs are more than welcome. The Crow’s Nest in the Square prides itself on being ‘The little Weymouth Bistro with big Spanish passion!’

The George Inn, Portland

Said to be the oldest inhabited building on the Isle of Portland, The George Inn exudes character and the quirky layout, selection of authentic ales and south facing beer garden all add to the charm of this dog friendly pub. The George prides itself on being a hub of the community with a fabulous events calendar, so be sure to check out the events page before you visit.

The Smugglers Inn, Osmington, Weymouth

The Smugglers Inn is a picture postcard pub, which dates back to the 13th century. It is known to have been the home of the leader of the most notorious gang of smugglers in the area during the 18th and 19th centuries. It is a beautiful pub with stunning views and sits amongst some of the best dog walks around. Well behaved dogs are welcome in the bar and outdoor areas and you will always find a jar of dog biscuits on the bar. This pub makes the best pit stop during a walk along the South West Coastal Path.

The Royal Standard, Weymouth

This is a lovely cosy and friendly pub which welcomes dogs both in the bar and in the garden. With big roaring fires in the winter and a lovely sunny patio for the summer, fantastic pub food and home brewed beer, it has all the trappings of the perfect country pub.