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

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

4.7

out of 5

7 nights

From

£615
View
Reserve today for only £25
View | Harbourside Landing, Weymouth

Weymouth, Dorset

Harbourside Landing

Coastal
Luxury
Wifi
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.6

out of 5

7 nights

From

£523
View
Reserve today for only £25
Dining Area | Coastal Gem, Weymouth

Weymouth, Dorset

Coastal Gem

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 4
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.9

out of 5

7 nights

From

£323
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

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

4.1

out of 5

7 nights

From

£277
View
Lovely single-storey barn conversion | Fossils’ End, Chickerell, near Weymouth

Chickerell, near Weymouth, Dorset

Fossils' End

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

5

out of 5

7 nights

From

£453
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

£839
View
Reserve today for only £25
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

Coastal
Wifi
Coast within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£327
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

£559
View
Delightful open plan living space | 5 Park Mews, Weymouth

Weymouth, Dorset

5 Park Mews

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 4
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£283
View
Reserve today for only £25
Cosy cottage with gravelled area to the front | Magnolia - St Anne’s Cottages, Chickerell, near Weymouth

Chickerell, near Weymouth, Dorset

St Anne's Cottages - Magnolia

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

5

out of 5

7 nights

From

£609
View
Reserve today for only £25
Coastal property in a stunning coastal location | The Old Boathouse, Portland, near Weymouth

Portland, near Weymouth, Dorset

The Old Boathouse

Coastal
Hot Tub
Wifi
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.3

out of 5

7 nights

From

£619
View
View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

Coastal
Wifi
Coast within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

7 nights

From

£417
View
Reserve today for only £25

Dog Friendly Cottages in Weymouth

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

4.7

out of 5

7 nights

From

£615
View
Reserve today for only £25
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

£437
View
Living room | Gwens House, Weymouth

Weymouth, Dorset

Gwens House

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 6
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

7 nights

From

£407
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

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

4.1

out of 5

7 nights

From

£277
View
Lovely single-storey barn conversion | Fossils’ End, Chickerell, near Weymouth

Chickerell, near Weymouth, Dorset

Fossils' End

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

5

out of 5

7 nights

From

£453
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

£839
View
Reserve today for only £25
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

£559
View
Cosy cottage with gravelled area to the front | Magnolia - St Anne’s Cottages, Chickerell, near Weymouth

Chickerell, near Weymouth, Dorset

St Anne's Cottages - Magnolia

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

5

out of 5

7 nights

From

£609
View
Reserve today for only £25
View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

Coastal
Wifi
Coast within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

7 nights

From

£417
View
Reserve today for only £25
Exterior | Glenmore Gardens, Weymouth

Weymouth, Dorset

Glenmore Gardens

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

7 nights

From

£417
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

4.6

out of 5

7 nights

From

£497
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

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

3

out of 5

7 nights

From

£397
View
Reserve today for only £25

Coastal Holiday Cottages in Weymouth

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

4.7

out of 5

7 nights

From

£615
View
Reserve today for only £25

Weymouth, Dorset

Flat One

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 7
  • 3 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

7 nights

From

£407
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

£437
View
Living room | Gwens House, Weymouth

Weymouth, Dorset

Gwens House

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 6
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

7 nights

From

£407
View
View | Harbourside Landing, Weymouth

Weymouth, Dorset

Harbourside Landing

Coastal
Luxury
Wifi
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.6

out of 5

7 nights

From

£523
View
Reserve today for only £25
Dining Area | Coastal Gem, Weymouth

Weymouth, Dorset

Coastal Gem

Coastal
Wifi
Pub within 1 mile
  • Sleeps up to 4
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.9

out of 5

7 nights

From

£323
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

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

4.1

out of 5

7 nights

From

£277
View
Living room | Cormorant View, Weymouth

Weymouth, Dorset

Cormorant View

Coastal
Wifi
Car parking on site
  • Sleeps up to 7
  • 4 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

3.8

out of 5

7 nights

From

£497
View
Lovely single-storey barn conversion | Fossils’ End, Chickerell, near Weymouth

Chickerell, near Weymouth, Dorset

Fossils' End

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

5

out of 5

7 nights

From

£453
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

£839
View
Reserve today for only £25
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

Coastal
Wifi
Coast within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£327
View
Exterior | Bridge View, Weymouth

Weymouth, Dorset

Bridge View

Coastal
Luxury
Wifi
  • Sleeps up to 8
  • 5 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

3.5

out of 5

7 nights

From

£895
View
Reserve today for only £25

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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