Osprey Holiday Cottages - Weymouth & Portland

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Osprey Holiday Cottages - Weymouth & Portland Osprey Holiday Cottages offer a range of self-catering cottages, coastal retreats and hideaways in Weymouth and on the Isle of Portland in Dorset

Kivel Cottage ready for action from 1st April 2026.
02/04/2026

Kivel Cottage ready for action from 1st April 2026.



It was a full on day today for us but we still managed to get a few good photos in of Nethercoombe House.
02/04/2026

It was a full on day today for us but we still managed to get a few good photos in of Nethercoombe House.

🎃 **Spooky Seaside Escapes Await!** 🕸️ Looking for a fang-tastic family getaway this October? Treat yourself to a cosy...
10/10/2025

🎃 **Spooky Seaside Escapes Await!** 🕸️

Looking for a fang-tastic family getaway this October?
Treat yourself to a cosy coastal break at **Seascape Apartment** and other stunning stays at Osprey Holiday Cottages.

👻 **Why Book Your Half-Term Stay?**
✅ Stylish, sea-view accommodation
✅ Autumn adventures & beach walks
✅ Local Halloween fun for all ages
✅ Warm, welcoming vibes for families & couples

🧙‍♀️ Don’t miss out — availability is vanishing fast!

📅 **Book now for October half-term**
🔗 Visit: [www.ospreycottages.co.uk](https://www.ospreycottages.co.uk/)

📍 Dorset’s hidden gem for autumn escapes!

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Appreciation post 👍Fab service from Blaze Fire Safety today, looking forward to working together more in the future.
02/10/2025

Appreciation post 👍
Fab service from Blaze Fire Safety today, looking forward to working together more in the future.

Vindelis Cottage: Vindelis Cottage is tucked away just a few yards from Chesil Beach at Portland, Dorset. Listen for the...
18/08/2025

Vindelis Cottage: Vindelis Cottage is tucked away just a few yards from Chesil Beach at Portland, Dorset. Listen for the peace and tranquillity of the sea or get ready to explore, Vindelis offers the perfect hideaway setting. With its own driveway for one car, this gorgeous property is behind its own private gateway. Ideally suited for small […]

The post Vindelis Cottage appeared first on Osprey Holiday Cottages.

https://www.ospreycottages.co.uk/holiday-letting/vindelis-cottage-portland-dorset/?utm_source=dlvr.it&utm_medium=facebook Book now!

Fisherman’s Cottage: Welcome to Fisherman’s Cottage, located near Chesil Beach in Portland, Dorset. Here, you’ll be so c...
18/08/2025

Fisherman’s Cottage: Welcome to Fisherman’s Cottage, located near Chesil Beach in Portland, Dorset. Here, you’ll be so close to Chesil Beach that you can hear the waves and enjoy the refreshing sea air. This beautifully renovated character cottage features two bedrooms and one bathroom, situated on the charming street of Brandy Lane just off Chesil Cove. You’re […]

The post Fisherman’s Cottage appeared first on Osprey Holiday Cottages.

https://www.ospreycottages.co.uk/holiday-letting/fishermans-cottage-holiday-accommodation-portland-dorset/?utm_source=dlvr.it&utm_medium=facebook Book now!

Carpe Diem: Just a few streets from the charming village of Easton on the Isle of Portland, Dorset – Carpe Diem is a spa...
18/08/2025

Carpe Diem: Just a few streets from the charming village of Easton on the Isle of Portland, Dorset – Carpe Diem is a spacious first-floor apartment offering comfort and convenience. With off-road parking available at the front of the house, you’ll have a hassle-free stay from the moment you arrive. The apartment features two versatile bedrooms, allowing […]

The post Carpe Diem appeared first on Osprey Holiday Cottages.

https://www.ospreycottages.co.uk/holiday-letting/carpe-diem-holiday-accommodation-portland-dorset/?utm_source=dlvr.it&utm_medium=facebook Book now!

The Octagon: The Octagon is a spacious and inviting family home in Weymouth, Dorset, with parking for two cars. Its uniq...
18/08/2025

The Octagon: The Octagon is a spacious and inviting family home in Weymouth, Dorset, with parking for two cars. Its unique octagonal design creates a stunning layout, making it truly one of a kind. Located right across from a charming sandy bay popular with swimmers, it’s also just minutes from Chesil Beach and Hamm Beach. You can […]

The post The Octagon appeared first on Osprey Holiday Cottages.

https://www.ospreycottages.co.uk/holiday-letting/the-octagon-house-self-catering-weymouth-dorset/?utm_source=dlvr.it&utm_medium=facebook Book now!

Dory Cottage: Dory Cottage on the Isle of Portland, Dorset offers a charming maritime experience, embodying a traditiona...
18/08/2025

Dory Cottage: Dory Cottage on the Isle of Portland, Dorset offers a charming maritime experience, embodying a traditional seaside theme. This historic cottage, with its three bedrooms accommodating up to five guests, features two full bathrooms. The proximity to the sea is so close that you can hear the soothing waves. Enjoy picturesque views from all front […]

The post Dory Cottage appeared first on Osprey Holiday Cottages.

https://www.ospreycottages.co.uk/holiday-letting/dory-cottage-portland-dorset-accommodation/?utm_source=dlvr.it&utm_medium=facebook Book now!

Portland View: Portland View is a roomy apartment that offers amazing views of two of the Isle of Portland’s lighthouses...
18/08/2025

Portland View: Portland View is a roomy apartment that offers amazing views of two of the Isle of Portland’s lighthouses. In fact, you’re so close you can walk there in a few minutes. It comes fully equipped with everything you could need for a relaxing getaway too. The apartment is located in one of the largest buildings […]

The post Portland View appeared first on Osprey Holiday Cottages.

https://www.ospreycottages.co.uk/holiday-letting/portland-view-self-catering-holiday-apartment-dorset/?utm_source=dlvr.it&utm_medium=facebook Book now!

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Opening Hours

Monday 09:00 - 17:00
Tuesday 09:00 - 17:00
Wednesday 09:00 - 17:00
Thursday 09:00 - 17:00
Friday 09:00 - 17:00

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