Weymouth Holiday Cottages

This coastal gem on the south coast with its picture-perfect beaches stretching along the bay, invites you to bask in the sun or even to take a stroll along the promenade. The bustling harbour, adorned with colourful boats, sets the scene for seafood feasts at waterfront eateries. Weymouth's Georgian architecture adds a touch of elegance to the town, while the lively esplanade teems with amusements, ice cream parlors, and the joyful sound of laughter. From the iconic Jurassic Coast to family-friendly attractions like Sandworld and the Sea Life Adventure Park, Weymouth offers a delightful mix of relaxation and adventure. Whether you're savouring fish and chips by the sea, exploring historic Nothe Fort, or simply unwinding with a sunset view, Weymouth promises an unforgettable coastal escape. Search our collection of hand-picked Weymouth holiday cottages for a classic British seaside escapade.

Weymouth harbour

Popular Holiday Cottages in Weymouth

Garden | The Pod, Weymouth

Weymouth, Dorset

The Pod

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

4.5

out of 5

7 nights

From

£515
View
Living room | Violet Bay, Weymouth

Weymouth, Dorset

Violet Bay

Coastal
Wifi
Enclosed Garden / Patio
  • Sleeps up to 5
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£499
View
Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

Coastal
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£925
View
Enclosed decked patio area | Samphire Cottage, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Samphire Cottage

Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

4.7

out of 5

7 nights

From

£649
View
Stylish open plan living space | Little Gem, Weymouth

Weymouth, Dorset

Little Gem

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.9

out of 5

7 nights

From

£325
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

Coastal
Luxury
Wifi
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4

out of 5

7 nights

From

£415
View
Charming holiday cottage close to Bincombe Down | Carpenters Cottage - Upwey Cottages, Weymouth
Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£345
View
Stylish 1st floor apartment | Cove View - Admirals Quarter, Weymouth

Weymouth, Dorset

Cove View

Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.7

out of 5

7 nights

From

£525
View
Welcoming living area | Rodwell Trail Cottage, Weymouth

Weymouth, Dorset

Rodwell Trail Cottage

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£689
View
Exterior | Old Milking Parlour, Osmington, near Weymouth

Osmington, near Weymouth, Dorset

Old Milking Parlour

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.6

out of 5

7 nights

From

£615
View
Living area | Hideaway House, Portland

Portland , Dorset

Hideaway House

Coastal
Wifi
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£615
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 3 pets allowed

4.1

out of 5

7 nights

From

£335
View

Dog Friendly Cottages in Weymouth

Garden | The Pod, Weymouth

Weymouth, Dorset

The Pod

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

4.5

out of 5

7 nights

From

£515
View
Living room | Violet Bay, Weymouth

Weymouth, Dorset

Violet Bay

Coastal
Wifi
Enclosed Garden / Patio
  • Sleeps up to 5
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£499
View
Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

Coastal
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£925
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

Coastal
Luxury
Wifi
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4

out of 5

7 nights

From

£415
View
Charming holiday cottage close to Bincombe Down | Carpenters Cottage - Upwey Cottages, Weymouth
Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£345
View
Exterior | Nemo’s Lodge, Portland

Portland, Dorset

Nemo’s Lodge

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

7 nights

From

£575
View
Exterior | Old Milking Parlour, Osmington, near Weymouth

Osmington, near Weymouth, Dorset

Old Milking Parlour

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.6

out of 5

7 nights

From

£615
View
Living area | Hideaway House, Portland

Portland , Dorset

Hideaway House

Coastal
Wifi
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£615
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 3 pets allowed

4.1

out of 5

7 nights

From

£335
View
Exterior | Pilgrims Rest, Weymouth

Weymouth, Dorset

Pilgrims Rest

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 3 pets allowed

4.6

out of 5

7 nights

From

£845
View
Charming 200 year old cottage  | Pebbles, Portland

Portland, Dorset

Pebbles

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.8

out of 5

7 nights

From

£449
View
Semi-detached holiday property  | Sparrows Nest, Preston, near Weymouth

Preston, near Weymouth, Dorset

Sparrows Nest

Coastal
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 3 pets allowed

4.1

out of 5

7 nights

From

£509
View

Coastal Holiday Cottages in Weymouth

Garden | The Pod, Weymouth

Weymouth, Dorset

The Pod

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

4.5

out of 5

7 nights

From

£515
View
Living room | Violet Bay, Weymouth

Weymouth, Dorset

Violet Bay

Coastal
Wifi
Enclosed Garden / Patio
  • Sleeps up to 5
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.9

out of 5

7 nights

From

£499
View
Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

Coastal
Luxury
Wifi
  • Sleeps up to 8
  • 4 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£925
View
Inviting living area | Apartment 3 Catherine House, Weymouth
Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

3.9

out of 5

7 nights

From

£435
View
Enclosed decked patio area | Samphire Cottage, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Samphire Cottage

Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

4.7

out of 5

7 nights

From

£649
View
Stylish open plan living space | Little Gem, Weymouth

Weymouth, Dorset

Little Gem

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.9

out of 5

7 nights

From

£325
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

Coastal
Luxury
Wifi
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4

out of 5

7 nights

From

£415
View
Charming holiday cottage close to Bincombe Down | Carpenters Cottage - Upwey Cottages, Weymouth
Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

7 nights

From

£345
View
Stylish 1st floor apartment | Cove View - Admirals Quarter, Weymouth

Weymouth, Dorset

Cove View

Coastal
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.7

out of 5

7 nights

From

£525
View
Welcoming living area | Rodwell Trail Cottage, Weymouth

Weymouth, Dorset

Rodwell Trail Cottage

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£689
View
Exterior | Nemo’s Lodge, Portland

Portland, Dorset

Nemo’s Lodge

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

7 nights

From

£575
View
Exterior | Old Milking Parlour, Osmington, near Weymouth

Osmington, near Weymouth, Dorset

Old Milking Parlour

Coastal
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.6

out of 5

7 nights

From

£615
View

Inspiration of things to see and do in our cottages in Weymouth

Stretching for three miles along the coast, Weymouth Beach is a stunning sandy expanse with crystal-clear waters. Enjoy sunbathing, sandcastle building, and swimming, or take a stroll along the promenade.With, a wide selection of holiday cottages in Dorset we have the ideal holiday home for you.

Here are the top 5 things to see and do from our cottages in Weymouth:

Sand Sculptures at Sandworld

Immerse yourself in the world of sand art at Sandworld, where talented sculptors craft intricate sculptures from the golden grains. Marvel at the creativity displayed in this unique and ever-changing exhibition.

Swannery in Abbotsbury

Take a short trip to Abbotsbury Swannery, where you can witness a spectacle of hundreds of mute swans. Stroll through this historic site and enjoy the charming presence of these elegant birds in a natural setting.

Nothe Fort Ghost Tours

Embark on a spine-tingling adventure with the Nothe Fort Ghost Tours. Explore the historic fort after dark, hearing tales of paranormal activity and mysterious occurrences in this atmospheric and unconventional tour.

Greenhill Gardens Miniature Railway

All aboard the Greenhill Gardens Miniature Railway! Experience a journey through beautifully landscaped gardens on a miniature steam train, offering a delightful and nostalgic escape for visitors of all ages.

Weymouth Old Harbour Underwater Sculpture Trail

Dive into a unique experience with the Weymouth Old Harbour Underwater Sculpture Trail. Snorkel or scuba dive to discover a series of underwater sculptures, adding an unconventional and artistic twist to exploring the marine environment off Weymouth's coast.

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