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  • A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
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A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth A brick house with green front door and white framed windows with bushes in front at Plain Sailing in Weymouth A living room with blue and yellow chairs a wooden coffee table and a television on a stand at Plain Sailing in Weymouth A living room with sofas a wooden coffee table and a TV on a stand at Plain Sailing in Weymouth A living room with a blue sofa yellow armchair wooden coffee table and framed pictures at Plain Sailing in Weymouth A living room with blue sofa yellow armchair wooden coffee table and grey sofa at Plain Sailing in Weymouth A living room with a blue sofa yellow armchair wooden coffee table and television at Plain Sailing in Weymouth A framed poster of Weymouth Harbour with colorful houses and a boat on the water on a white wall at Plain Sailing in Weymouth A dining room with a wooden table set with plates wine glasses and brown chairs next to a rustic cabinet and kitchen visible through an archway at Plain Sailing in Weymouth A dining room with a wooden table set for six and brown chairs at Plain Sailing in Weymouth A dining room with a wooden table set for six next to an open doorway leading to a kitchen at Plain Sailing in Weymouth A dining area with four brown chairs around a wooden table a wall clock and a multicolored cabinet at Plain Sailing in Weymouth A kitchen area with a sink washing machine and wooden cabinets next to a dining area with a wooden table and orange chairs at Plain Sailing in Weymouth A kitchen with built-in double oven and wooden cabinets next to a dining area with a wooden table and four chairs at Plain Sailing in Weymouth A kitchen with wooden cabinets an oven a washing machine a dishwasher a microwave and a gas stove at Plain Sailing in Weymouth A kitchen with wooden cabinets built in oven microwave gas hob and various appliances at Plain Sailing in Weymouth A kitchen with wooden cabinets a gas stove a dishwasher and a window with a patterned blind at Plain Sailing in Weymouth A hallway with carpeted stairs and white bannisters with wooden doors at Plain Sailing in Weymouth A bathroom with a pedestal sink round mirror toilet and towel rack at Plain Sailing in Weymouth A bedroom with a double bed, two bedside tables with lamps, a window with curtains, and a painting on a brown accent wall at Plain Sailing in Weymouth A bedroom with a bed made with white and pink bedding two rolled towels on the bed a window with curtains a wooden dresser with a round mirror on the wall at Plain Sailing in Weymouth A bedroom with a bed with pink cushions and blankets and two wooden closets at Plain Sailing in Weymouth A bedroom with a bed with pink pillows and towels on it a black dresser with a vase and a round mirror on the wall at Plain Sailing in Weymouth A bathroom with a shower area blue tiled wall white sink and toilet at Plain Sailing in Weymouth A bedroom with two single beds a white dresser and a window with blue blinds at Plain Sailing in Weymouth A bedroom with two single beds white furniture and blue accent wall at Plain Sailing in Weymouth A bedroom with a white bed and folded towels on it a window with a blue blind a clothes rack with hangers and a round mirror on the wall at Plain Sailing in Weymouth A bedroom with a single bed with white and blue pillows a wooden door and a glass on a table at Plain Sailing in Weymouth A bedroom with a bed with rolled towels two bedside tables a chair and sloped ceilings at Plain Sailing in Weymouth A bedroom with a wooden bed a dresser with a television a mirror and a window with curtains at Plain Sailing Weymouth A bedroom with a wooden bed, green blanket, nightstands with lamps, a window with curtains, and an armchair at Plain Sailing in Weymouth A bedroom with a wooden bed with green cushions and blanket two wooden doors and a white dresser with a television at Plain Sailing in Weymouth A bedroom with a double bed with green bedding and rolled towels an armchair a bedside table with lamp and abstract artwork on the wall at Plain Sailing in Weymouth A bathroom with a skylight window a towel rail a toilet and a glass shower enclosure at Plain Sailing in Weymouth A stairway with white banisters and gray carpet and a framed picture on the wall at Plain Sailing in Weymouth An outdoor patio area with a grey dining table and six chairs against a brick wall and wooden fence at Plain Sailing in Weymouth An outdoor patio with a table set with a bottle of wine and glasses a fruit basket a light blue garden shed and a wooden fence at Plain Sailing in Weymouth An outdoor patio area with gravel ground a blue metal bench potted plants and a table with chairs at Plain Sailing in Weymouth A garden pathway with gravel and white lattice pergola leading to a patio with a table and chairs at Plain Sailing in Weymouth A garden area with a white wooden pergola gravel ground a shed potted plants and a patio table with chairs at Plain Sailing in Weymouth A garden with a shed bench pergola table and chairs at Plain Sailing in Weymouth A residential area with multiple brick houses and solar panels on the roof near a body of water at Plain Sailing in Weymouth

Plain Sailing

Weymouth, Dorset (Ref. 1153879)

Customer rating

4.8★

How reviews work

A property's star rating is the average of the star ratings received from guests that wish for their review to be published

Dream Cottages rating

  • 6 Guests

  • 3 Bedrooms

  • 2 Bathrooms

  • Pets Yes

  • Show on map

Features

  • Off road parking
  • Garden / Patio
  • Cot available
  • Highchair available
  • Pub/shop < 1 mile
  • Washing machine
  • Dishwasher
  • Broadband / WiFi

Reviews & Ratings

Accuracy of the listing
Cleanliness
Comfort
Facilities and Maintenance

* Based on a combined average customer score

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12 Customer Review(s)

  • Sally

    “The level of cleaning was shocking on arrival.”

    Surfaces like draws, TV unit, Skirting boards, window sills, ornaments, hadn't been dusted in a long, long time. Toilets with no cleaner in, shower traps full of hair, shower screens not been cleaned in long time. Draws were clothes go gad to be hovered out 1st before we could put stuff away. Some Towels stained, even after we re washed them. Attention to hoovering and mopping poor, didn't both with corners or moving furniture. Did call & report to office. House itself and location perfect, well ...

    Surfaces like draws, TV unit, Skirting boards, window sills, ornaments, hadn't been dusted in a long, long time. Toilets with no cleaner in, shower traps full of hair, shower screens not been cleaned in long time. Draws were clothes go gad to be hovered out 1st before we could put stuff away. Some Towels stained, even after we re washed them. Attention to hoovering and mopping poor, didn't both with corners or moving furniture. Did call & report to office. House itself and location perfect, well equipped and well decorated.

    - Sally, July 2025

    Thank you for your feedback regarding your recent stay at Plain Sailing and I am delighted that you found the house and location perfect for your holiday. I am disappointed to hear that the standard of cleaning did not meet with your expectations. All aspects of housekeeping are carried out by Dream Cottages own team so I have raised the issue with them to ensure it is all carried out to a higher standard in the future. Kind regards ‘The Owner’. Property Owner

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Summary

  • Over three floors
  • Three bedrooms: 1 x second-floor king size with Smart TV and en-suite walk-in shower, basin, heated towel rail and WC, 1 x double, 1 x twin, x1 cot
  • Shower room with walk-in shower, basin, heated towel rail and WC
  • Cloakroom with basin and WC
  • Kitchen/diner
  • Sitting room
  • Gas central heating
  • Electric double oven, gas hob, microwave, washing machine, dishwasher, kettle and toaster fridge freezer
  • 2 x Smart TV, super fast WiFi
  • Fuel and power inc. in rent
  • Bed linen and towels inc in rent
  • Cot and high chair included
  • Allocated Off-road parking for 1 car
  • Enclosed rear garden with patio and furniture
  • One well-behaved dog welcome
  • Sorry, no smoking
  • Shop and pub 0.2 miles, beach 0.5 miles on foot.

The property

Plain Sailing is a beautifully-presented holiday home situated in the heart of the wonderful seaside town of Weymouth, Dorset.

This pet-friendly retreat offers a perfect escape for those looking to explore the charming surroundings of Weymouth.

With its prime location and amenities, Plain Sailing is the ideal choice for families and groups of friends seeking a relaxing coastal getaway.

Step inside to find a home that oozes charm and comfort.

Spread over three floors, this delightful retreat boasts three bright and airy bedrooms.

The second-floor double bedroom offers a comfortable experience with its own en-suite and Smart TV.

The additional double and twin bedrooms provide ideal spaces to rest.

The well-equipped kitchen/diner is the perfect spot to whip up delicious meals and share stories over dinner, while the sitting room beckons you to unwind in front of the Smart TV, making it the ideal place to relax after a day of sightseeing.

When the sun is shining, step outside where the rear garden offers a private sanctuary for you to enjoy the fresh sea air on the patio, complete with furniture for al fresco dining or simply soaking up the sunshine.

There is a shed available at the property for the outdoor adventurers of the group to store bikes and sports gear.

Discover the wonders of Weymouth and the Isle of Portland during your stay at Plain Sailing.

Experience the beauty of Weymouth Bay with a ferry tour, visit the fascinating Portland Museum, and spend a day getting to know the adorable residents at Portland Alpacas.

For history buffs, a trip to Nothe Fort is a must, or simply relax on the golden sands of Weymouth Beach.

Indulge in delicious meals at the local restaurants offering fresh seafood and traditional dishes.

Enjoy the property's close proximity to the start of the Rodwell Trail recreational path which is perfect for family cycling as it provides a pleasant, traffic free 3.5km walk or bicycle ride from Westham Bridge in the heart of Weymouth town centre to Ferry Bridge.

From there you can continue 0.8km along Portland Beach Road to the Chesil Beach Visitor Centre.

Venture to Dorchester for a day of exploration, where you can embark on a Jurassic Safari, visit The Dinosaur Museum, or marvel at the wildlife at Kingston Maurward Animal Park and Gardens.

No visit to Dorset would be complete without a trip to the iconic Corfe Castle, offering stunning views and a glimpse into the area’s rich history.

With so much to see and do in the surrounding area, Plain Sailing provides the perfect base for an unforgettable coastal getaway.

Note: This property has a Good Housekeeping bond of £350.

View on map

About the location

WEYMOUTH

Dorchester 7 miles; Bridport 17 miles.

The popular resort of Weymouth makes an outstanding year-round holiday destination, with a wide variety of attractions on offer, appealing to all tastes and ages. The glorious golden sandy beaches have excellent facilities for all kinds of watersports, whilst from the picturesque, bustling harbour you can take regular fishing trips. A short drive takes you to Portland Harbour, and the rugged “Isle” of Portland, linked to Weymouth by the dramatic Chesil Beach. Visit Dorchester, Thomas Hardy’s “Casterbridge”, only 7 miles away, or take a journey along the scenic coastal road and call in at Abbotsbury Swannery and Subtropical Gardens. Alternatively, just head down to West Bay - the views of the stunning Dorset Heritage Coastline are not to be missed!

Please note: There is a shed available at the property solely for guests to store bikes and sports gear (at guests risk).

This property offers the following short breaks:

  • Winter
  • Off-season
  • Last minute
  • Christmas