Trinity Road · Weymouth Harbour · Dorset
Two harbourside homes on the Jurassic Coast, a bridge away from the beach.
Sailor's Watch sleeps six across two floors with a sun room and a secret walled garden. Waterside sleeps four at water level with a bay window on the boats. Both sit on Trinity Road, the quiet side of the old harbour, opposite the fishing boats and the George Inn.
The cottages
Weymouth's inner harbour is the working heart of the town: fishing boats, a lifting bridge, pubs on the quay and a terrace of tall painted houses along Trinity Road on the Rodwell side. Both of our holiday cottages are here, so you wake to masts and gulls, cross the Town Bridge for the beach, and are on the South West Coast Path within ten minutes.
A two-floor maisonette above the harbour with a south-facing sun room, a range-cooker kitchen and, at the back, a walled garden nobody would guess was there. The master bedroom's window frames the boats.
A ground-floor apartment with one step in from the street and the harbour filling the bay window. Open-plan living, a king-size bedroom with its own shower room, and a twin that turns into a super-king on request.
Both cottages face Weymouth's inner harbour from Trinity Road. Watch the Town Bridge lift from the window.
Over the bridge and along the Esplanade to three miles of sheltered, shallow, sandy bay.
One well-behaved dog is welcome in each cottage. The Rodwell Trail starts a short walk away.
Heating, power, bed linen and towels. Travel cot and highchair on request. Wi-Fi throughout.
A Zone L on-street parking permit comes with each cottage, subject to availability, with a council car park close by.
Brewers Quay, Hope Square and the harbourside pubs are two minutes away; the town centre is five.
Sailor's Watch · sleeps 6
Sailor's Watch takes up the first and second floors of a brick-and-render house on Trinity Road. The name is earned: the sitting room's bay window is level with the masts, and from the master bedroom above you can watch the bridge open for the boats.
The first floor is where you will spend your evenings. A bright sitting room in deep teal looks over the water; behind it a kitchen and dining room, with a range cooker, a big blue island and a table for six, opens through folding glass doors into a south-facing sun room. Beyond that is the surprise: an enclosed, high-walled garden with a terrace and soft turf, completely private and warm out of the wind.
Upstairs are three bedrooms and a shower room. The super-king master has the harbour view; a king-size room and a twin sit at the quieter rear. The family bathroom with its bath is on the first floor. Contemporary throughout, but the house keeps its old bones: wooden stairs, painted panelling and windows that have looked at the same water for two centuries.
Live availability and prices are on Dream Cottages, who manage the bookings. Short breaks and full weeks, year round.
Check availabilityPhotos do not do it justice.
Kelly, guest review, June 2025
Everything that you need for your stay is there.
Karen, guest review, September 2023
We have just spent two weeks in Sailor's Watch and it was the perfect place for an amazing holiday.
Simone, guest review, July 2026
Live availability and prices are on Dream Cottages, who manage the bookings. Short breaks and full weeks, year round.
Check availabilityWaterside · sleeps 4
Waterside is the easy one. One step in from Trinity Road and you are in a bright, open-plan room with the harbour on the other side of the glass. It suits couples, a family of four, or two friends with a dog who want the town, the beach and the coast path without ever needing the car.
The living space runs front to back: an armchair and television in the bay, two sofas in the middle, and a dining table by the kitchen, which is fitted in cream with a wall of cobalt-blue tiles and everything you would expect, including a dishwasher, a washer and a tumble dryer. Shelves of books and a small collection of nautical odds and ends give it the feel of a well-loved home rather than a rental.
Three steps up, the king-size bedroom has its own shower room and a painting of the boats you can see from the window. The second bedroom is a twin that can be made up as a super-king if you ask, and shares a bathroom with both a bath and a shower. Renovated throughout, quiet at the back, and moments from the Town Bridge.
Perfect location, everything in short walking distance.
Guest review
Well equipped and spotlessly clean.
Guest review
George III came here for the sea air fourteen summers running. He had a point.
Weymouth beach in July. Photograph: Edward Betts, CC BY-SA 3.0
Beautiful Weymouth
Weymouth was England's first royal resort. George III made it his summer home from 1789, trundled into the sea in a bathing machine, and the town built a mile of pale Georgian terraces along the bay to keep him company. The terraces are still there, so is the sand, and so is the sunshine: Weymouth averages more than 1,900 hours a year, among the highest in Britain.
Three miles of gently shelving sand in a sheltered bay: safe swimming, Punch and Judy, pedalos, and a promenade of Georgian hotels watched over by the 1887 Jubilee Clock.
Photo: Chase me ladies, I'm the Cavalry, CC BY-SA 4.0
A working fishing harbour lined with pubs and fish restaurants. The 1930 bascule bridge lifts on the hour to let the yachts through; your cottage is the best seat in the house.
Photo: Andrew Bone, CC BY 2.0
A Victorian coastal fort with tunnels, big guns and a 360-degree view from the ramparts, set in gardens on the headland at the end of Trinity Road's peninsula.
Photo: Colin Smith, CC BY-SA 2.0
Henry VIII's crumbling artillery fort of 1539, now a romantic ruin with a tea garden, looking across Portland Harbour to the island.
Photo: Colin Smith, CC BY-SA 2.0
The old Weymouth-to-Portland railway, now a leafy traffic-free path for walking, cycling and dogs, running from the town to Ferrybridge and the start of Chesil Beach.
Photo: Neil Owen, CC BY-SA 2.0
Hope Square's former brewery, the Tudor House, Sea Life on the seafront, boat trips along the Jurassic Coast, and RSPB reserves at Radipole Lake and Lodmoor within the town itself.
Photo: Richard Symonds, CC BY 3.0The surrounding area
The Jurassic Coast runs from Exmouth to Studland and Weymouth sits at its centre, which makes the cottages a base for the whole of it. East are the limestone arches and coves of Purbeck. West is the great shingle bank of Chesil and the swannery at Abbotsbury. South, over the causeway, is the Isle of Portland.
The most photographed rock on the south coast: a natural limestone arch above a shingle beach, reached by a steep path from the cliff-top car park. Go early or go at sunset.
Photo: Saffron Blaze, CC BY-SA 3.0
A near-perfect circle of sea scooped out of the cliffs, with a village of thatched cottages, a fossil forest on the ledges and a cliff walk over to Durdle Door.
Photo: public domain
Eighteen miles of shingle sorted by the sea from pea-sized at Bridport to fist-sized at Portland, sheltering the Fleet lagoon. Storm-watching in winter, seals and terns in summer.
Photo: Rosser1954, CC BY-SA 4.0
A honey-stone village with the only managed colony of nesting mute swans in the world, a monastic tithe barn, and subtropical gardens sheltered in a valley above the beach.
Photo: Paul Gillett, CC BY-SA 2.0
The tied island's rocky southern tip: a lighthouse you can climb, Pulpit Rock, quarries turned sculpture parks, and some of the best sea-cliff climbing and bird-watching in England.
Photo: Peter Glyn, CC0
For a full day out: Corfe Castle's ruin above its village, the steam railway to Swanage, and the chalk stacks of Old Harry at the eastern end of the Jurassic Coast.
Photo: Simaron, CC BY-SA 2.0Cygnets hatch at Abbotsbury from mid-May, the coast path is at its greenest and the beach is empty enough to have to yourself.
Sand sculptures on the beach, the seafood festival on the harbour, carnival week in August and long evenings on the quay watching the boats come in.
Warm sea, quiet roads, fossil hunting after the first storms and speed sailing in Portland Harbour, where the 2012 Olympic sailing was held.
Storm-watching at Chesil, log-fire pubs in the old town, a bracing walk to Sandsfoot and a harbour that goes back to being a fishing village.
Getting here and good to know
Sailor's Watch, over two upper floors with three bedrooms and a garden, suits families and groups of up to six. Waterside is on the ground floor with two bedrooms and suits couples, a family of four or friends who want to be on the harbour with minimal stairs.
Yes, one well-behaved dog is welcome in each cottage. The Rodwell Trail, the Nothe and the winter beach are all good dog walks from the door.
A travel cot and a highchair are available in both cottages; ask when you book. Bed linen and towels are included for everyone.
A Zone L on-street permit comes with each cottage, subject to availability. Spaces on Trinity Road can be busy at peak times, and there is a council car park a short walk away.
Both cottages are managed and booked through Dream Cottages. Use the Check availability buttons to see live dates and prices and book securely online.
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Sleeps 6 · 3 bedrooms · 2 bathrooms · sun room and walled garden · one dog welcome
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