Destination guide

Holiday lettings in Weymouth and Portland district

Located in the vibrant Dorset, Weymouth and Portland district is a popular destination for travellers of all interests, ranging from yachting and sailing enthusiasts to history buffs and families. No matter how you’re looking to spend your retreat, you’ll find boundless opportunities in Weymouth and Portland district, along with a wide selection of holiday lettings to make the most of your experience.


Heritage near Weymouth and Portland district holiday homes

Plenty of heritage sites and museums in Weymouth and Portland district offer a fascinating glimpse into the past in the area. Holiday lettings put you in reach of locations like the Weymouth Museum, a history museum with unique exhibits and artefacts of development in Weymouth, and the Jubilee Clock Tower, a century-old freestanding clock tower that commemorates the Golden Jubilee of Queen Victoria. History buffs will also enjoy the Tudor House Museum, a Tudor home with a local history museum, and Maiden Castle, an Iron Age hillfort with multiple ramparts dating back to the first-century BC.

Food & drink 

Sample famous delicacies in Weymouth and Portland district

Weymouth and Portland district is a premier foodie destination with plenty of its own unique food concoctions for an unforgettable dining experience. Several dishes are unique to the area, such as Dorset Apple Cake, a sweet cake with spices and clotted cream, and Portland lamb, a local breed of sheep that’s rare in the UK and noted for its fine texture and delicious flavour. Another must-try dish is Dorset knobs, a bread dough with additional sugar and butter that’s shaped by hand and baked multiple times for a distinctive taste and texture. To experience the one-of-a-kind delicacies of Weymouth and Portland district, visit one of the restaurants or cafes near your holiday rental and indulge.

Family friendly

Family fun near Weymouth and Portland district holiday homes

Families with children will enjoy the interesting kid-friendly attractions in Weymouth and Portland district. Family-friendly holiday homes give you access to places like Sandworld, a unique gallery with massive sand sculptures and a sand pit for hands-on creations, and Lodmoor Country Park, a spacious park with trails, playgrounds, a mini-train ride and an aquarium. RSPB Lodmoor, a nature reserve with exotic wildlife, native birds and a country park, and Lorton Meadows Conservation Centre & Nature Reserve, a grassland reserve with harbour views and an abundance of native species, are also great for children.

Good for couples

Romantic holiday homes in Weymouth and Portland district

The beautiful scenery and magnificent architecture of Weymouth and Portland district make it an ideal destination for a romantic retreat. Holiday cottages can be found near intimate locations like Bennetts Water Gardens, a water lily garden with ponds, lakes, Japanese-style water features and a history museum, and Greenhill Gardens, a public garden near the beach with nature trails and colourful blooms. Sandsfoot Caste, a fortress ruin site with peaceful gardens and sweeping sea views, and Ringstead Bay, a picturesque beachfront area with footpaths, clifftops and rolling hills, are wonderful places to spend the day reconnecting.

How many holiday rentals are available around Weymouth and Portland District?

Our 2020 accommodation listings offer a large selection of 653 holiday lettings around Weymouth and Portland District. From 82 houses to 2 chalets, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent a seaside property in Weymouth and Portland District?

Drinking in cool ocean air, basking in the sunshine and decidedly losing all track of time. Now that's the sort of awesome vacay you deserve. HomeAway has 246 holiday rentals by the beach to choose from. Looking for a different atmosphere? See if any of our other properties tickle your fancy. Our options for this destination include:

  • 150 beach holiday accommodation options.
  • 96 rural holiday accommodation options.
  • 76 village holiday accommodation options.

Can I stay in Weymouth and Portland District in a large group?

There's nothing quite like meeting up with old work colleagues or spending a few weeks with extended family in an exciting new destination. And the best thing, HomeAway has options big enough for the whole squad. Why not have a look at the 95 cottage holiday rentals listed here? They're the top option for big groups of travellers. In and around the area, the rental properties that can house bigger groups include:

  • On the lookout for properties that can hold 6 people? We have 176 that will be perfect. Prices begin from just £79 per night.
  • If you have 5 in your group, you'll be delighted to discover that there are 88 holiday rentals that are suitable. Prices begin at just £65 per night.
  • Seeking out places for rent to suit 8 people? You'll be happy to discover we have 60 that'll be ideal. You can grab one from just £83 per night.

So don't fret! When you travel with us you can take your aunt, your grandpa and all your buddies to Weymouth and Portland District.