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If you’re looking to buy a holiday let in Weymouth, you may be considering several different areas. At Dream Cottages, we can lend our expertise and offer advice on the best locations.

With over 35 years of experience of holiday letting in Weymouth and Dorset, we know the best places to invest.

Chances are, you’re probably looking for a location or property that will provide year-round profitable income in Weymouth. Read on for our guide to the top 10 places to invest in a holiday let, in Weymouth.

Holiday letting vs long term letting

First, there are many benefits to holiday letting vs long-term letting. For instance, with holiday letting you can register for business rates if you’re welcoming guests for more than 140 days of the year. Therefore, you will not need to pay council tax on the property. Instead, you will pay business rates.

Furthermore, if the rateable value of your property is less than £12,000 per annum, you can claim small business rates relief. What this means is that you would pay no business rates or council tax if eligible.

Our New Property Consultants can assist with your business case and provide a free pricing appraisal estimating projected income. This is based on other holiday lets in the same area, with the same property specification.

At Dream Cottages, we can also a provide mortgage letter to assist with your property purchase.

Weymouth as a holiday destination

The seaside town of Weymouth has been a popular destination since the 1800 when King George III popularised sea bathing.

In 2023, The Times crowned Weymouth Beach as the best beach in Britain which is a huge accolade. With golden sands, clear shallow waters, donkey rides, fish and chips, ice-creams and arcades all within a half a mile radius, it’s the perfect location for a holiday.

Areas outside of the immediate beach area have their own perks and benefits too, however of which we will explore. All districts of Weymouth are only a maximum of a 20-minute drive to the main Weymouth Beach.

Sutton Poyntz

The village of Sutton Poyntz is a beautiful one complete with a duck pond and village pub The Springhead. Property in this village is very popular so doesn’t come up often. Although priced at a higher price scale compared to other properties in and around Weymouth, the return on investment is also on the higher scale.

With walks into the countryside surrounding the stunning properties and easy access into Weymouth town centre, Sutton Poyntz is a great location to buy a holiday let.


Just outside of Sutton Poyntz is Preston which covers the Bowleaze Beach area of Weymouth.

Properties here are large and of the pricier range, however with a pebble beach on the doorstep this is a great location to purchase a holiday let. There is quick access to Weymouth town centre and attractions nearby.


The village of Upwey is home to the Upwey Wishing Well and is home to some of the most beautiful riverside properties. With lots of walks surrounding the the village, this area is great for dog walks.

The county town of Dorchester is just 20 minutes from Upwey, as is Weymouth. Upwey is a great place to buy a holiday let in Weymouth, as it’s just enough away from the hustle and bustle whilst still being very connected.


Lodmoor is mainly a residential area however resides in great walking distance to the beach and town. Property is cheaper here than other districts, greatly connected with bus routes and supermarkets.

Lodmoor Country Park is a great day out and guests can enjoy a ride-a-long train, Weymouth SEA LIFE Adventure Park, Sandworld and other attractions here.


If you’re looking for a property that’s well connected to public transport but in a quieter area, Radipole is a great area to invest in property in. A stone’s throw away is Radipole Lake and Radipole Gardens which houses a great play area for kids, tennis courts and green spaces.


Broadwey is an area that’s within quick commutable distance to Dorchester and within 20 minutes distance of Weymouth and its amenities. Properties in this area are typically less expensive and have great gardens.


This area is mainly residential but has great amenities of a small shopping centre. Here you can find a pub, takeaway shops and a village shop.

Weymouth town centre is also walkable from here around the Radipole reserve lake footpath that begins just outside of Southill.


Chickerell village has grown substantially over the last few years. Here you’ll find two great village pubs, often with live music, great roast dinners and themed evenings. Alongside the village shop, there’s excellent connections to Weymouth town centre with bus links.

This village is extremely family friendly with a great park and playing field in the centre. This area is great for pets to enjoy too.

Chickerell is a great place to buy a holiday let if you’re looking for a quieter area to enjoy as your second home also.

Wyke Regis

Wyke Regis is a busy residential area that sits along the main Portland road. Here you’ll find pubs, the fleet and Chesil Beach is only a short walk away.

Property in this area is slightly cheaper than other areas and has many little beaches surrounding it. Weymouth town centre is only a 15 minute drive away.


The area of Rodwell is where the Dream Cottages office resides and is close to Weymouth Harbour. You’ll find plentiful free parking in the residential streets surrounding, the Nothe Gardens and Fort, shops and close walking distance to town. The Rodwell trail connects to Wyke Regis and onto Portland making a scenic walk to town.

This area is a great place to purchase a property for holiday letting and as a second home.

Book a visit

If you’d like to discuss purchasing a property for holiday letting, the Dream Cottages team are here to help. We’re happy to support you on every step of the journey and can even attend property viewings with you.

Book a visit, or download your free owner pack today.

Please Note: The information contained in this article was accurate at the time of writing, based on our research. Rules, criteria and regulations change all the time, so please contact our prospective new owner team if you’d like to hear how. Nothing in this article constitutes the giving of financial, tax or legal advice to you; please consult your own professional advisor (accountant, lawyer etc). in this regard. If we have referred within the article to a third-party provider of unregulated holiday let mortgages, this is due to the fact that such mortgages aren’t currently regulated by the FCA. 

As a helpful reminder, your home may be repossessed if you do not keep up repayments on a mortgage, so again anything you decide to do in this particular area this is one on which you should take your own professional advice on too, as we aren’t providing and can’t provide you with this.