Filter
Property Type
Property Features
Sleeps

Holiday Homes in Portland, Dorset

Self-Catering Holiday Cottages in Portland

Portland, in Dorset, offers a delightful self-catering escape, with an array of holiday chalets, log cabins, and small villas perfect for a relaxing stay. Nestled 8 kilometers south of Weymouth, Portland is celebrated for its coastline and unique geology, with the Portland Island—a prominent limestone block—being a major attraction. Its rich fauna and flora make it a haven for ornithologists studying rare bird species. Visitors can explore Portland Castle and the Governor’s Garden, both offering stunning views. Its coastal charm and connection to nature make Portland an ideal destination for a rejuvenating cottage holiday.

Booking your holiday accommodation in Portland early is recommended for the best choice of holiday rentals.

Rose Cottage, Dorset, England
Viewed 9× this week

Rose Cottage

Tincleton, Dorset ~12 miles from Portland
Sleeps 3–6 3 Bedrooms 🚫 No Dogs
Next Available 23/03 to 27/03/2026
Facilities
WiFi Open fire Coffee machine Dishwasher Washing machine Tennis Garden BBQ
Type of Holiday
No dogs allowed
Weekly from £950 – £1,895
View
Glenacres, Dorset, England
Viewed 15× this week

Glenacres

Chideock , Dorset ~20 miles from Portland
Sleeps 5–12 5 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 21/03 to 23/05/2026
Facilities
WiFi Woodburner Open fire Coffee machine Microwave Dishwasher Washing machine Pool
Type of Holiday
No dogs allowed Special celebrations Group welcome
Weekly from £4,900 – £6,650
View
Tincleton Lodge, Dorset, England
Viewed 10× this week

Tincleton Lodge

Tincleton, Dorset ~12 miles from Portland
Sleeps 5–10 5 Bedrooms 🚫 No Dogs
Next Available 23/03 to 27/03/2026
Facilities
Open fire Garden BBQ
Type of Holiday
No dogs allowed Group welcome
Weekly from £1,495 – £2,895
View
Symondsbury Manor, Dorset, England
Viewed 10× this week No booking fee

Symondsbury Manor

Bridport, Dorset ~19 miles from Portland
Sleeps 11–22 11 Bedrooms 🐾 2 Dogs 🎉 Celebrations
Next Available 22/03 to 27/03/2026
Facilities
WiFi Woodburner Microwave Dishwasher Washing machine Games room Garden BBQ
Type of Holiday
2 dogs welcome Special celebrations Hen Parties Group welcome Weddings
Weekly from £5,600 – £7,500
View
The Fishing Lodge, Dorset, England
Viewed 14× this week

The Fishing Lodge

Sydling St Nicholas, Dorset ~14 miles from Portland
Sleeps 1–4 2 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 21/03 to 27/03/2026
Facilities
WiFi Open fire Microwave Dishwasher Washing machine Garden BBQ Parking
Type of Holiday
No dogs allowed Special celebrations
Weekly from £800 – £1,800
View
Langford Valley Barn, Dorset, England
Viewed 15× this week

Langford Valley Barn

Dorchester, Dorset ~14 miles from Portland
Sleeps 4–8 4 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 21/03 to 03/04/2026
Facilities
WiFi Woodburner Coffee machine Microwave Dishwasher Washing machine Games room Garden
Type of Holiday
No dogs allowed Special celebrations Corporate events
Weekly from £1,200 – £3,000
View
Stonebank Annexe, Chickerell, Dorset, England
Viewed 7× this week

Stonebank Annexe, Chickerell

Chickerell, Dorset ~5 miles from Portland
Sleeps 2–4 2 Bedrooms 🐾 1 Dog
Next Available 21/03 to 09/05/2026
Facilities
WiFi Coffee machine Microwave Garden Parking
Type of Holiday
1 dogs welcome
Weekly from £420 – £660
View
Private Rural Lodge, Wrackleford Estate, Dorset, England
Viewed 11× this week

Private Rural Lodge, Wrackleford Estate

Stratton, Dorset ~13 miles from Portland
Sleeps 4–8 4 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 21/03 to 03/04/2026
Facilities
WiFi Woodburner Open fire Coffee machine Microwave Dishwasher Washing machine Games room
Type of Holiday
No dogs allowed Special celebrations Corporate events
Weekly from £1,100 – £4,000
View


Cottages, Apartments & Lodges in Portland, Dorset, England

RuralHomeStays.Com features holiday home(s) within or close to Portland, enjoy browsing through the available options. We hope you find the perfect holiday house for you in Portland, Dorset.


Portland: A Coastal Haven in Dorset

Portland is a small town located in the southernmost area of the county of Dorset in England. The town is located around 8 kilometres to the south of resort Weymouth, and together they form the borough of Portland and Weymouth. It is because of Portland’s connectivity with beaches and other mainland towns that tourists come here in large numbers to enjoy self-catering holidays.

Natural Attractions in Portland

Owing to its coastal location, Portland consists of a wide range of fauna and flora. The coastline region along with quarries present here has been designated as special sites of scientific interest. In most seasons, you can find ornithologists from different regions conducting research on some rare species of birds.

Exploring the Wonders of Portland

Some of the attractions here include the Portland Island, which is more of a limestone block, connected to the mainland of Dorset by a narrow gateway. It is the same limestone which has been used in different important buildings present in the area. Other important attractions here include Portland Castle and the Governor’s Garden, which offer excellent views to visitors.

Self-Catering Accommodation in Portland

The town also consists of self-catering accommodation options like holiday chalets, log cabins, and small villas that offer a comfortable stay to travelers.

Updated