Top 10 places to buy a holiday let in Weymouth
If you’re looking to buy a holiday let in Weymouth, you may be considering several different areas. At Dream...
Are you ready to turn a property into a thriving income-generating holiday let? This comprehensive holiday let business guide will walk you through every step from choosing the right location to furnishing your property, meeting legal requirements, managing guests and increasing bookings.
Whether you’re considering letting a cottage in Dorset or exploring the wider UK holiday rental market, this article gives you the expert insights you need.
A holiday let business can be a rewarding and profitable way to utilise a second home or investment property. With the rising demand for staycations and short-term rentals, more property owners are entering this market. But starting a successful holiday let business takes planning, preparation and ongoing management.
Before you dive in, make sure you understand what running a holiday let involves from guest expectations to local regulations and tax considerations. There are a lot of other things to consider when starting a holiday let business. We have over 30 years of experience, so you are welcome to chat with our experts.
To find out more, contact us via email dreamownerrelations@dream-cottages.co.uk or call 01305 789000 option 2.
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The first and one of the most important decisions you’ll make in your holiday let business journey is choosing the location of your property. The setting of your holiday let directly influences its rental value, seasonal appeal and occupancy rates.
Seaside or countryside? Coastal homes often attract summer bookings, while rural cottages can be booked year-round.
Accessibility matters. If you plan to manage the property yourself, consider how far it is from your permanent home.
Local attractions and amenities. Proximity to beaches, national parks, restaurants or historic sites can make your property more desirable.
Use our guide on Top 10 places to buy a holiday let in Weymouth for inspiration when evaluating locations.

Well-chosen, durable, and stylish furnishings are critical. Guests expect comfort but you also need materials that stand up to frequent use. Choose your furnishings wisely, taking into account the volume of guests, durability and good quality furniture that will save you money in a long run.
Here’s what to focus on:
Comfortable beds and quality linens
Stylish, durable seating and tables
Practical kitchen equipment
Consider the tastes of your target market a luxury holiday home might benefit from premium finishes, while a family-friendly cottage needs practical, easy-to-clean furniture.

Certain features and facilities add a huge value to a holiday property. If you need some guidance in deciding what would best suit for your property, we can help.
Hot tubs and swimming pools — often booked up quickly.
Outdoor spaces and parking — especially valuable in rural settings.
Fast Wi-Fi and good mobile reception — now expected as standard.
These upgrades may require extra maintenance, so weigh the potential return against ongoing costs.

There’s growing demand for pet-friendly accommodations as more travellers consider pets part of the family. Accepting pets can increase bookings — particularly for small and mid-sized properties.
We currently have more than 200 pet friendly properties in our portfolio. Make sure you set clear pet policies and consider features such as enclosed gardens or easy-to-clean flooring.

Maintaining cleanliness is essential for positive guest reviews and repeat bookings. Reliable cleaning services ensure smooth turnovers and less stress for owners.
If you prefer not to manage cleaning yourself, explore professional support. Our managed services including cleaning, laundry and maintenance can help streamline operations.
We know that some owners prefer to greet their guests in person, but some live overseas and don’t have that option. Most of our properties have key safes. It saves trouble if guests are arriving late at night or decide to leave very early in the morning.

Welcome packs are a nice gesture and don’t have to be pricey! They save the trip to the shop for your guests and usually it just might be tea, coffee, sugar, fresh jug of milk, locally made cookies or a loaf of bread.
If your cottage is on a farm, you may want to supply fresh eggs or vegetables. If you are planning to set up a luxury holiday home, a welcome pack is a necessity and will be expected to have some additional goodies in it.

An information pack acts as a guest’s go-to resource with essential details:
Property instructions and appliance guides
Emergency contacts
Local attractions and restaurant recommendations
You could even partner with local businesses to offer guest discounts — a great way to enhance the guest experience and support the local community.

Before welcoming guests, ensure you comply with all UK legal and safety obligations:
Fit smoke and carbon monoxide detectors throughout the property.
Provide a clear accessibility statement where applicable.
Adhere to Furniture and Furnishings (Fire) Safety Regulations.
These steps protect guests and help you avoid penalties.
Understanding the tax side of your holiday let business is crucial. For example, properties classified as Furnished Holiday Lets (FHL) historically offered tax advantages, though government changes terminated this from April 2025.
Local tax rules may also influence whether you pay business rates or council tax, so it’s worth getting professional advice.

Starting a holiday let business is a rewarding venture, but success doesn’t come overnight. With the right property, thoughtful planning, thoughtful guest amenities, strong marketing and reliable management, your holiday let can flourish year after year.
To dig even deeper into managing your holiday home profitably, check out our posts on holiday let tax essentials and holiday let management options
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