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Holiday Cottages in Weymouth with Swimming Pools

8 properties found

A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland

Bear's Apartment

Castletown, Portland, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£561

A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
Offer

Baytree Lodge

Osmington, Dorset

12 Guests
5 Beds
Pet Friendly
Wifi

for 7 nights

From

£3510

A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester

Agua de Plata, 26 Wakeling Island, Silverlake

Dorchester, Dorset

8 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£810

A balcony with glass table and chairs overlooking buildings and a body of water at Panoramic View in Castletown Portland

Panoramic View

Castletown, Portland, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£526

A lighthouse and white buildings with a stone wall and grassy area at Old Higher Lighthouse Branscombe Lodge Portland Bill

Portland Bill, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£617

A white building with a stone wall and flowers in front and a lighthouse behind at Old Higher Lighthouse Stopes Cottage in Portland Bill

Portland Bill, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£648

A house with ivy on one side a paved driveway and a porch with wooden furniture at Deer Leap House in Moreton

Deer Leap House

Moreton, Dorset

15 Guests
7 Beds
Pet Friendly
Wifi

for 7 nights

From

£2211

A two story house with brick lower walls and pebble dash upper walls with multiple windows and a hedge in front at Deer Leap Cottage in Moreton

Deer Leap Cottage

Moreton, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£737

Perfect for unwinding or having fun for the whole family, a holiday cottage with a swimming pool is always a popular choice among holidaymakers. Browse our selection of Weymouth cottages with swimming pools, and if you are interested please do not hesitate to book as these are amongst our most high in demand properties.

Why a holiday cottage in Weymouth with a swimming pool?

After an exhausting day rambling the South West Coast Path or exploring the attractions of Nothe Fort and the Sea Life Centre, what better way to unwind than with a dip in the hot tub or a gentle swim in your own private pool? Kids will love it too - they’ll spend endless hours splashing about and having fun, whatever the weather!  

Places to visit in Dorset

There are Dorset attractions and activities to suit all tastes, no matter where you choose to stay. Lovers of the wonderful Jurassic coastline might fancy staying in the seaside resorts of West Bay or Lyme Regis, where you can enjoy the golden sands and gentle waters as well as seeking out ancient fossils and feature landmarks.

If you’re after a rural retreat, then consider staying at the quaint village of Burton Bradstock or Lulworth, where glorious green countryside and pretty thatched cottages come in the many. 

Types of Holiday

Choose from our array of different types of holiday to find a cottage that suits you down to the ground. From Weymouth cottages with hot tubs, to dog-friendly cottages and family breaks to cottages with a sea view and those with an open fire, we hope you can find a property that ticks all your boxes. 


If you need any assistance finding a holiday cottage in Weymouth with a swimming pool, our team of friendly travel experts are ready to answer your call.

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