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 | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

Coastal
Luxury
Wifi
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

4.1

out of 5

7 nights

From

£937
View
Stylish open plan living space | Little Gem, Weymouth
Customers' Choice

Weymouth, Dorset

Little Gem

Coastal
Wifi
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£315
View
Cosy cottage with gravelled area to the front | Magnolia - St Anne’s Cottages, Chickerell, near Weymouth
Customers' Choice

Chickerell, near Weymouth, Dorset

St Anne’s Cottages - Magnolia

Pets stay free
Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£691
View
Hot tub with fantastic sea views | Lloyds Cottage, Portland, near Weymouth
Customers' Choice

Portland, near Weymouth, Dorset

Lloyds Cottage

Coastal
Hot Tub
Wifi
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.8

out of 5

7 nights

From

£892
View
Patio view | The Annex, Weymouth

Weymouth, Dorset

The Annex

Coastal
Wifi
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£385
View
Exterior | Roselands, Dorchester

Dorchester, Dorset

Roselands

Pets stay free
Coastal
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.5

out of 5

7 nights

From

£671
View
Dining Area | Coastal Gem, Weymouth
Customers' Choice

Weymouth, Dorset

Coastal Gem

Coastal
Wifi
Car parking on site
  • 4 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£355
View
Terrace | Bay View 34, Weymouth

Weymouth, Dorset

Bay View 34

Coastal
Luxury
Swimming pool
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£581
View
Living room | Cormorant View, Weymouth

Weymouth, Dorset

Cormorant View

Coastal
Wifi
Car parking on site
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.5

out of 5

7 nights

From

£577
View
View | Harbourside Landing, Weymouth
Customers' Choice

Weymouth, Dorset

Harbourside Landing

Coastal
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£489
View
Exterior | Newstead Cottage, Weymouth

Weymouth, Dorset

Newstead Cottage

Pets stay free
Coastal
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

7 nights

From

£621
View

Dog Friendly Cottages in Weymouth

Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

Coastal
Luxury
Wifi
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

4.1

out of 5

7 nights

From

£937
View
Cosy cottage with gravelled area to the front | Magnolia - St Anne’s Cottages, Chickerell, near Weymouth
Customers' Choice

Chickerell, near Weymouth, Dorset

St Anne’s Cottages - Magnolia

Pets stay free
Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£691
View
Exterior | Roselands, Dorchester

Dorchester, Dorset

Roselands

Pets stay free
Coastal
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.5

out of 5

7 nights

From

£671
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

Coastal
Luxury
Wifi
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

3.3

out of 5

7 nights

From

£479
View
Exterior | Newstead Cottage, Weymouth

Weymouth, Dorset

Newstead Cottage

Pets stay free
Coastal
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

7 nights

From

£621
View
Exterior | Nemo’s Lodge, Portland

Portland, Dorset

Nemo’s Lodge

Pets stay free
Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 1 Pet

3.2

out of 5

7 nights

From

£449
View
Garden | The Pod, Weymouth
Customers' Choice

Weymouth, Dorset

The Pod

Pets stay free
Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.8

out of 5

7 nights

From

£545
View
View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

Pets stay free
Coastal
Wifi
Coast within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£415
View
Living room | Violet Bay, Weymouth
Customers' Choice

Weymouth, Dorset

Violet Bay

Pets stay free
Coastal
Wifi
Enclosed Garden / Patio
  • 5 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

3.6

out of 5

7 nights

From

£515
View
Living area | Hideaway House, Portland
Customers' Choice

Portland, Dorset

Hideaway House

Coastal
Wifi
Car parking on site
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

5

out of 5

7 nights

From

£657
View

Coastal Holiday Cottages in Weymouth

Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

Coastal
Luxury
Wifi
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 2 Pets

4.1

out of 5

7 nights

From

£937
View
Stylish open plan living space | Little Gem, Weymouth
Customers' Choice

Weymouth, Dorset

Little Gem

Coastal
Wifi
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£315
View
Cosy cottage with gravelled area to the front | Magnolia - St Anne’s Cottages, Chickerell, near Weymouth
Customers' Choice

Chickerell, near Weymouth, Dorset

St Anne’s Cottages - Magnolia

Pets stay free
Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£691
View
Hot tub with fantastic sea views | Lloyds Cottage, Portland, near Weymouth
Customers' Choice

Portland, near Weymouth, Dorset

Lloyds Cottage

Coastal
Hot Tub
Wifi
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.8

out of 5

7 nights

From

£892
View
Patio view | The Annex, Weymouth

Weymouth, Dorset

The Annex

Coastal
Wifi
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£385
View
Exterior | Roselands, Dorchester

Dorchester, Dorset

Roselands

Pets stay free
Coastal
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.5

out of 5

7 nights

From

£671
View
Dining Area | Coastal Gem, Weymouth
Customers' Choice

Weymouth, Dorset

Coastal Gem

Coastal
Wifi
Car parking on site
  • 4 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£355
View
Terrace | Bay View 34, Weymouth

Weymouth, Dorset

Bay View 34

Coastal
Luxury
Swimming pool
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£581
View
Living room | Cormorant View, Weymouth

Weymouth, Dorset

Cormorant View

Coastal
Wifi
Car parking on site
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.5

out of 5

7 nights

From

£577
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

Coastal
Luxury
Wifi
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

3.3

out of 5

7 nights

From

£479
View
View | Harbourside Landing, Weymouth
Customers' Choice

Weymouth, Dorset

Harbourside Landing

Coastal
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£489
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 on your next short break 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.

More Popular Holiday Destinations in Dorset

Lyme Regis cottages

Bridport cottages

Swanage cottages

Sherborne cottages

Shaftesbury cottages

Explore