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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

(Ref. 1153879)

Weymouth, Dorset Show on map

Customer rating 4.6

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

Sykes rating

  • 6 Guests

  • 3 Bedrooms

  • 2 Bathrooms

  • Pets: Yes

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
  • All reviews
  • location (8)
  • home (7)
  • lovely (7)
  • well (7)
  • house (6)
  • equipped (6)

15 Customer Reviews

  • "Plain Sailing suited us as the house was neat, tidy, comfortable, well equipped, and has private parking."

    And it’s within easy walking distance of the town and the beach.

    Thank you very much for the feedback regarding your recent stay at Plain Sailing. I am pleased that you liked the property and found the location really suitable for your holiday. Kind regards “The Owner” Property Owner

    Reviewed by Graham5.0★Oct 2025

  • "The location is ideal for walking to the sea front, saving on time a money for parking."

    If we stayed here again, we would take our own clean bed linen.

    I am sorry to hear that you have had some issues with the cleanliness of the bed linen. All housekeeping is carried out by Dream Cottage’s own team, so we do have a note in the guest book to say that if things aren’t to your satisfaction then to contact the Dream cottage’s office immediately to have this resolved. So that this issue would not then impair the enjoyment of your holiday. Kind regards “The Owner.” Please note as from the 31/10/25 the property will be cleaned and linen provided by a different company, with the aim of improving the standard of housekeeping. Property Owner

    Reviewed by Elizabeth2.0★Sep 2025

  • "Well located."

    10 minute slow stroll on the flat to the centre of Weymouth. Comfortable seating in the lounge and plenty of side tables. Good size dining table Bathrooms are good. Shower in first floor, family bathroom is large. Garden includes a dining table and chairs and 2 relaxing chairs. Was quite a suntrap in September. Unfortunately, although the rest of the house seemed clean, the kitchen is crying out for a deep clean. There were significant greasy smears and stains on then kitchen cupboard doors

    Thank you for your feedback regarding your stay at Plain Sailing. I am glad you found the property and location to your liking. Please note that since your stay the kitchen has had an extensive clean and a complete kitchen refit is booked in for January 2026. Kind regards “The Owner”. Property Owner

    Reviewed by Gillian4.0★Sep 2025

  • "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 equipped and well decorated.

    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

    Reviewed by Sally4.0★Jul 2025

  • "Excellent accommodation & location, very well equipped, we did find in the ..."

    Excellent accommodation & location, very well equipped, we did find in the welcome pack the bar of chocolate had a chunk missing & the only other issue was nothing to facilitate recycling, we will certainly return and recommend, D A Wright

    Thank you very much for taking the time to review your holiday at Plain Sailing. I am so glad that you liked the property, with regard to the issue with the welcome pack I have made the suppliers aware of this. Unfortunately Dorset Council are not currently able to offer recycling to business waste customers but this will be available in the future. Kind regards, ‘The Owner’ Property Owner

    Reviewed by David5.0★Jun 2025

  • "Great stay."

    Good location.

    Thank you for your 5 star review. Best wishes, The Owner. Property Owner

    Reviewed by Cameron5.0★May 2025

  • "The house is beautifully decorated and very clean."

    We felt very comfortable in this cosy home. Everything was well equipped and well thought out would definitely stay here again. We are planning to book this again for next year. We’ve stayed in places in Weymouth before always had issues with parking. There were no issues with this place parking was allocated and considerate neighbours. When we arrived, there was a beautiful welcome hamper, and most of the essentials to get us by were provided. This was a lovely surprise and set the tone for a wonderful holiday.

    Thank you very much for the lovely review of your stay at Plain Sailing, I am so pleased you enjoyed your holiday. It would be great to welcome you back in the future! Best wishes, The Owner. Property Owner

    Reviewed by Tom5.0★May 2025

  • "Lovely property, felt like home straight away."

    Very well equipped and love the decor. The location is ideal for getting out and about, both on foot and by car. The town centre and sea front are only 15 mins walk away and the old harbour is well worth a visit for relaxing and watching the world go by. Plenty to do in the area, for all ages and the scenery is spectacular so driving was not a chore. The property would benefit from a blind on the lounge window as our dog is extremely protective and barked at every car, person and bird passing the window! The Velux window in the ensuite could also do with a blind to keep the sun out as it got quite hot in there and in the master bedroom We will definitely return and went home chilled and rested after a great few days away, didn't want to leave! I would have no hesitation in recommending Plain Sailing to others

    Thank you for taking the time to review your stay at Plain Sailing, I am glad to hear that you liked the property and had an enjoyable stay. Kind regards ‘The Owner’ Property Owner

    Reviewed by Tracey5.0★May 2025

  • "Beautiful house."

    Immaculate inside and out. Lovely decoration. Super welcome gift. My only gripe was after we left on the way home I called Sykescottages to report something three times on way home. Gave up in the end after being past from pillar to post and then being on hold for 25 mins at the end! Gave up in the end. . Perhaps you would like to call me for more information. ?

    Thank you very much for your review of Plain Sailing, it is rewarding to hear that you liked the house so much. I note your difficulty in trying to contact Sykes Cottages and have made the managing agents aware of this. Kind regards ‘The Owner’ Property Owner

    Reviewed by Teresa5.0★Apr 2025

  • "Lovely holiday home."

    We had everything we needed. Close to town and lovely walks. We shall certainly be back.

    Thank you for your positive feedback regarding your recent holiday. I am so glad you enjoyed your stay at Plain Sailing and it would be a pleasure to welcome you back in the future. Best wishes from ‘The Owner’ Property Owner

    Reviewed by Catherine5.0★Mar 2025

  • "Plain Sailing is a lovely property which is well equipped and in a good location for the town centre and a great base to explore the area."

    The furniture is very comfortable and the decor very tasteful and relaxing. The patio is sheltered and catches the afternoon sun which was an added bonus. The house is cosy and warm and the heating is easy to adjust. We enjoyed it so much we extended our stay. The house being on three floors with quite steep stairs might not be ideal for less mobile but we managed ok. Would highly recommend.

    Thank you for your positive feedback. I am delighted that you enjoyed yourselves so much that you decided to extend your stay. Best wishes from ‘The Owner’ Property Owner

    Reviewed by Karen5.0★Feb 2025

  • "Very comfy and everything you need there plus the extra bits like the welcome box, milk and washing up liquid, bin bags."

    Loved our stay

    Thank you very much for the positive feedback regarding your stay at Plain Sailing. I am so glad that you enjoyed your stay and found the house to be very comfortable. Kind regards ‘The Owner’ Property Owner

    Reviewed by Caroline5.0★Oct 2024

  • "The location of the property is excellent - less than 10 minutes walk from the town and sea front."

    The kitchen had everything we needed for our stay and the Happy Hamper and pint of milk were a lovely extra. Maybe this is an age thing, but staying there did confirm our dislike of the latest fashion for naked light bulbs and barely there lampshades as we did struggle with the lighting in the evenings. Also, I have never had to log onto my own TV account in a holiday home before and had to contact the holiday company after we got home to ask them to delete it from the TV as I forgot to do so! Otherwise, a lovely place to stay.

    Thank you very much for taking the time to review your stay at ‘Plain Sailing’. I have noted your comments regarding the lighting and would like to advise that it was specifically chosen to compliment the contemporary, relaxed decor of the property. It is not necessary for guests to log into their own personal TV accounts just to watch normal television, but of course guests can log into their own personal streaming services on the Smart TV’s that are provided, if desired. I am delighted that overall you found ‘Plain Sailing’ a lovely place to stay. Kind regards ‘The Owner’ Property Owner

    Reviewed by Jane4.0★Aug 2024

  • "This was a lovely property with all the home comforts, very modern, clean and a nice garden."

    Ideal location about less than a 10 minute walk into Weymouth. Welcome hamper was an added bonus which we all enjoyed. Would definately come back to this property.

    Thank you very much for the positive feedback regarding your recent stay at Plain Sailing. I am so glad to hear that you had such an enjoyable time and it would be great to welcome you back in the future. Best wishes from ‘The Owner’ Property Owner

    Reviewed by Richard5.0★Aug 2024

  • "Wonderful holiday home!"

    Thank you for your feedback, glad you enjoyed your stay! Property Owner

    Reviewed by Katherine5.0★Jul 2024

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This property is part of the Dream Cottages collection.
Over 350 carefully selected and perfectly located properties, helping you create your perfect holiday.

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.

Where you’ll be staying

View on map

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!

View more holiday cottages in Weymouth

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
Flexible cancellation terms

If you cancel before 12 noon , get all of your money back:

  • Rent
  • Extras
  • Fees

excluding the Flexible Cancellation fee and any insurance premium.

There are a small number of circumstances where you can’t use Flexible Cancellation. See the Flexible Cancellation Terms that apply.