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

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

4.7

out of 5

14 Nov•7 nights

£811
View
Living area | Pebble Cottage, Weymouth

Weymouth, United Kingdon

Pebble Cottage

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

4.7

out of 5

14 Nov•7 nights

£557
View
Exterior | Bridge View, Weymouth

Weymouth, Dorset

Bridge View

Coastal
Luxury
Wifi
  • 8 Guests
  • 5 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.6

out of 5

3 Jan•7 nights

£897
View
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

Coastal
Wifi
Coast Within 1 Mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.6

out of 5

21 Feb•7 nights

£373
View
Living room | Harbourhill, Chickerell, near Weymouth
Customers' Choice

Chickerell, near Weymouth, Dorset

Harbourhill

Coastal
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

9 Oct•7 nights

£681
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

14 Jan•7 nights

£323
View
Exterior | Old Milking Parlour, Osmington, near Weymouth
Customers' Choice

Osmington, near Weymouth, Dorset

Old Milking Parlour

Coastal
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

23 Nov•7 nights

£617
View
Living room | Freshwater Bay View, Portland
Customers' Choice

Portland, Dorset

Freshwater Bay View

Coastal
Wifi
Car Parking On Site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

5

out of 5

9 Oct•7 nights

£657
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

Coastal
Wifi
Car Parking On Site
  • 5 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 3 Pets

4.1

out of 5

27 Nov•7 nights

£273
View
Delightful open plan living space | 5 Park Mews, Weymouth
Customers' Choice

Weymouth, Dorset

5 Park Mews

Coastal
Wifi
Pub Within 1 Mile
  • 4 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

5 Dec•7 nights

£273
View

Dog Friendly Cottages in Weymouth

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 Feb•7 nights

£601
View
Exterior | Old Post Office Cottage, Weymouth

Weymouth, Dorset

Old Post Office Cottage

Coastal
Wifi
Car Parking On Site
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 2 Pets

20 Nov•7 nights

£607
View
Living room | Harbourhill, Chickerell, near Weymouth
Customers' Choice

Chickerell, near Weymouth, Dorset

Harbourhill

Coastal
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

9 Oct•7 nights

£681
View
Exterior | Old Milking Parlour, Osmington, near Weymouth
Customers' Choice

Osmington, near Weymouth, Dorset

Old Milking Parlour

Coastal
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

23 Nov•7 nights

£617
View
Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

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

3.5

out of 5

2 Nov•7 nights

£941
View
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

Coastal
Wifi
Car Parking On Site
  • 5 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 3 Pets

4.1

out of 5

27 Nov•7 nights

£273
View
View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

Coastal
Wifi
Coast Within 1 Mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

5

out of 5

5 Nov•7 nights

£417
View
Semi-detached holiday property  | Sparrows Nest, Preston, near Weymouth

Preston, near Weymouth, Dorset

Sparrows Nest

Coastal
Car Parking On Site
Enclosed Garden / Patio
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 3 Pets

4.8

out of 5

13 Nov•7 nights

£343
View

Coastal Holiday Cottages in Weymouth

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

4.7

out of 5

14 Nov•7 nights

£811
View
Living area | Pebble Cottage, Weymouth

Weymouth, United Kingdon

Pebble Cottage

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

4.7

out of 5

14 Nov•7 nights

£557
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 Feb•7 nights

£601
View
Exterior | Bridge View, Weymouth

Weymouth, Dorset

Bridge View

Coastal
Luxury
Wifi
  • 8 Guests
  • 5 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.6

out of 5

3 Jan•7 nights

£897
View
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

Coastal
Wifi
Coast Within 1 Mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.6

out of 5

21 Feb•7 nights

£373
View
Exterior | Old Post Office Cottage, Weymouth

Weymouth, Dorset

Old Post Office Cottage

Coastal
Wifi
Car Parking On Site
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 2 Pets

20 Nov•7 nights

£607
View
Living room | Harbourhill, Chickerell, near Weymouth
Customers' Choice

Chickerell, near Weymouth, Dorset

Harbourhill

Coastal
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.6

out of 5

9 Oct•7 nights

£681
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

14 Jan•7 nights

£323
View
Exterior | Old Milking Parlour, Osmington, near Weymouth
Customers' Choice

Osmington, near Weymouth, Dorset

Old Milking Parlour

Coastal
Wifi
Car Parking On Site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.9

out of 5

23 Nov•7 nights

£617
View
Garden | Jasmine Cottage, Osmington

Osmington, Dorset

Jasmine Cottage

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

3.5

out of 5

2 Nov•7 nights

£941
View

See more cottages in Weymouth

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