Portland Cottages

Immerse yourself in the picturesque beauty of Portland with a holiday cottage rental from cottages.com. Indulge in a serene escape surrounded by stunning landscapes, quaint villages, and enchanting coastal views. Our handpicked selection of charming cottages offers the perfect blend of comfort and character, ensuring an unforgettable holiday. Embark on scenic walks along rugged coastlines, explore historic landmarks, and discover hidden gems within this vibrant seaside destination. Whether you're seeking a romantic retreat or a fun-filled family adventure, our Portland cottages provide the ideal base for your holiday. Escape the hustle and bustle of everyday life and unwind in the tranquillity of your private sanctuary. With spacious living areas, well-equipped kitchens, and cosy bedrooms, our cottages offer all the comforts of home. Immerse yourself in the local culture by visiting traditional pubs, sampling fresh seafood delicacies, or browsing through charming boutiques nearby. Book your dream holiday with us today and let Portland's natural beauty work its magic on you. We guarantee an exceptional experience that will leave you longing to return to our idyllic cottages time and time again.

Portland Lighthouse

Popular Holiday Cottages in Portland

View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

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

4.5

out of 5

7 nights

From

£417
View
Reserve today for only £25
Comfortable living area | Elizabethan House, Portland

Portland, Dorset

Elizabethan House

Coastal
Wifi
Enclosed Garden / Patio
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.3

out of 5

7 nights

From

£875
View
Charming 200 year old cottage  | Pebbles, Portland

Portland, Dorset

Pebbles

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

4.8

out of 5

7 nights

From

£467
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

4.3

out of 5

7 nights

From

£619
View
Wonderful holiday cottage with sea views | Mallams, Portland, near Weymouth

Portland, near Weymouth, Dorset

Mallams

Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.7

out of 5

7 nights

From

£327
View
Reserve today for only £25
Living room | Violet Bay, Weymouth

Weymouth, Dorset

Violet Bay

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

4.4

out of 5

7 nights

From

£497
View
Exterior | Mallams Art House, Portland, near Weymouth

Portland, near Weymouth, Dorset

Mallams Art House

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

4

out of 5

7 nights

From

£403
View
Welcoming living area | Rodwell Trail Cottage, Weymouth

Weymouth, Dorset

Rodwell Trail Cottage

Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4

out of 5

7 nights

From

£688
View
Living area | Pebble Cottage, Weymouth

Weymouth, United Kingdon

Pebble Cottage

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

5

out of 5

7 nights

From

£367
View
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

Coastal
Wifi
Coast within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.8

out of 5

7 nights

From

£327
View
Spacious house in the prestigious Admirals Quarter | Nothe View - Admirals Quarter, Weymouth

Weymouth, Dorset

Nothe View

Luxury
Wifi
Car parking on site
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.9

out of 5

7 nights

From

£655
View
Living area | Hideaway House, Portland

Portland, Dorset

Hideaway House

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

4.8

out of 5

7 nights

From

£565
View

Dog Friendly Cottages in Portland

View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

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

4.5

out of 5

7 nights

From

£417
View
Reserve today for only £25
Comfortable living area | Elizabethan House, Portland

Portland, Dorset

Elizabethan House

Coastal
Wifi
Enclosed Garden / Patio
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.3

out of 5

7 nights

From

£875
View
Charming 200 year old cottage  | Pebbles, Portland

Portland, Dorset

Pebbles

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

4.8

out of 5

7 nights

From

£467
View
Living room | Violet Bay, Weymouth

Weymouth, Dorset

Violet Bay

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

4.4

out of 5

7 nights

From

£497
View
Exterior | Mallams Art House, Portland, near Weymouth

Portland, near Weymouth, Dorset

Mallams Art House

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

4

out of 5

7 nights

From

£403
View
Living area | Hideaway House, Portland

Portland, Dorset

Hideaway House

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

4.8

out of 5

7 nights

From

£565
View
Living room | Cornerstone, Portland

Portland, Dorset

Cornerstone

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

3

out of 5

7 nights

From

£397
View
Reserve today for only £25
Exterior | Nemo’s Lodge, Portland

Portland, Dorset

Nemo’s Lodge

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

3

out of 5

7 nights

From

£437
View
Reserve today for only £25
Exterior | Trevina, Portland, nr. Weymouth

Portland, near Weymouth, Dorset

Trevina

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

4.2

out of 5

7 nights

From

£277
View

Coastal Holiday Cottages in Portland

View | Chesil Vista, Fortuneswell, Portland

Fortuneswell, Portland, Dorset

Chesil Vista

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

4.5

out of 5

7 nights

From

£417
View
Reserve today for only £25
Comfortable living area | Elizabethan House, Portland

Portland, Dorset

Elizabethan House

Coastal
Wifi
Enclosed Garden / Patio
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.3

out of 5

7 nights

From

£875
View
Charming 200 year old cottage  | Pebbles, Portland

Portland, Dorset

Pebbles

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

4.8

out of 5

7 nights

From

£467
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

4.3

out of 5

7 nights

From

£619
View
Wonderful holiday cottage with sea views | Mallams, Portland, near Weymouth

Portland, near Weymouth, Dorset

Mallams

Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.7

out of 5

7 nights

From

£327
View
Reserve today for only £25
Living room | Violet Bay, Weymouth

Weymouth, Dorset

Violet Bay

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

4.4

out of 5

7 nights

From

£497
View
Exterior | Mallams Art House, Portland, near Weymouth

Portland, near Weymouth, Dorset

Mallams Art House

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

4

out of 5

7 nights

From

£403
View
Terrace | Bay View 34, Weymouth

Weymouth, Dorset

Bay View 34

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

7 nights

From

£507
View
Welcoming living area | Rodwell Trail Cottage, Weymouth

Weymouth, Dorset

Rodwell Trail Cottage

Coastal
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4

out of 5

7 nights

From

£688
View
Living area | Pebble Cottage, Weymouth

Weymouth, United Kingdon

Pebble Cottage

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

5

out of 5

7 nights

From

£367
View
Living area | Seagulls Lookout, Weymouth

Weymouth, Dorset

Seagulls Lookout

Coastal
Wifi
Coast within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.8

out of 5

7 nights

From

£327
View
Spacious house in the prestigious Admirals Quarter | Nothe View - Admirals Quarter, Weymouth

Weymouth, Dorset

Nothe View

Luxury
Wifi
Car parking on site
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • 0 Pets

4.9

out of 5

7 nights

From

£655
View

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

Embark on a unique and memorable adventure in the charming town of Portland with cottages.com. We bring you the top 5 things to see and do, curated especially for travellers seeking off-the-beaten-path experiences. Uncover extraordinary moments in Portland with cottages.com – because true adventures happen outside ordinary itineraries. With, a wide selection of holiday cottages in Dorset we have the ideal holiday home for you.

Portland Bill Lighthouse

Visit the iconic Portland Bill Lighthouse, a striking white tower perched on the rugged cliffs. Explore the visitor centre, learn about its maritime significance, and enjoy panoramic views of the coastline.

Portland Castle

Explore Portland Castle, a well-preserved 16th-century coastal fortress managed by English Heritage. Discover its history, climb its battlements, and enjoy interactive exhibits.

Chesil Beach

Spend time on Chesil Beach, a shingle barrier stretching along the coast. Walk along the pebbles, enjoy beachcombing, and admire the stunning views of the sea and the Isle of Portland.

Portland Museum

Learn about the island's history and heritage at Portland Museum. Discover artefacts, photographs, and exhibits that showcase the local maritime, geology, and social history.

Portland Sculpture and Quarry Trust

Visit Tout Quarry Sculpture Park and Nature Reserve, where you can explore an abandoned stone quarry transformed into an art park with unique sculptures set against the backdrop of nature.

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