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

Coastal property in a stunning coastal location | The Old Boathouse, Portland, near Weymouth

Portland, near Weymouth, Dorset

The Old Boathouse

Coastal
Hot Tub
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.8

out of 5

9 Jan7 nights

£641
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

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

4.8

out of 5

2 Oct7 nights

£577
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

9 Apr7 nights

£851
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

16 Nov7 nights

£617
View
Charming 200 year old cottage  | Pebbles, Portland
Customers' Choice

Portland, Dorset

Pebbles

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

4.8

out of 5

30 Oct7 nights

£473
View
Living area | Beach Gem, Weymouth

Weymouth, Dorset

Beach Gem

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

5

out of 5

7 Jan7 nights

£297
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

3 Dec7 nights

£323
View
Spacious house in the prestigious Admirals Quarter | Nothe View - Admirals Quarter, Weymouth
Customers' Choice

Weymouth, Dorset

Nothe View

Luxury
Wifi
Car Parking On Site
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.9

out of 5

7 Jan7 nights

£801
View
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

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

4.7

out of 5

29 Jan7 nights

£357
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

4.4

out of 5

3 Oct7 nights

£621
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 Nov7 nights

£417
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

3.4

out of 5

29 Oct7 nights

£941
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

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

4.8

out of 5

2 Oct7 nights

£577
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

16 Nov7 nights

£617
View
Charming 200 year old cottage  | Pebbles, Portland
Customers' Choice

Portland, Dorset

Pebbles

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

4.8

out of 5

30 Oct7 nights

£473
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

4.4

out of 5

3 Oct7 nights

£621
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 Nov7 nights

£417
View
Exterior | Roselands, Dorchester

Dorchester, Dorset

Roselands

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

4.9

out of 5

8 Jan7 nights

£691
View
Living room | Violet Bay, Weymouth
Customers' Choice

Weymouth, Dorset

Violet Bay

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

4.2

out of 5

18 Jan7 nights

£513
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

3.4

out of 5

29 Oct7 nights

£941
View
Coastal property in a stunning coastal location | The Old Boathouse, Portland, near Weymouth

Portland, near Weymouth, Dorset

The Old Boathouse

Coastal
Hot Tub
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.8

out of 5

9 Jan7 nights

£641
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

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

4.8

out of 5

2 Oct7 nights

£577
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

9 Apr7 nights

£851
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

16 Nov7 nights

£617
View
Charming 200 year old cottage  | Pebbles, Portland
Customers' Choice

Portland, Dorset

Pebbles

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

4.8

out of 5

30 Oct7 nights

£473
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

3 Dec7 nights

£323
View
Spacious house in the prestigious Admirals Quarter | Nothe View - Admirals Quarter, Weymouth
Customers' Choice

Weymouth, Dorset

Nothe View

Luxury
Wifi
Car Parking On Site
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.9

out of 5

7 Jan7 nights

£801
View
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

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

4.7

out of 5

29 Jan7 nights

£357
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

4.4

out of 5

3 Oct7 nights

£621
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.

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