Places to stay in Fortuneswell, Dorset

Fortuneswell is a village in Underhill on the Isle of Portland, in Dorset. It lies on steeply sloping land on the northern edge of the island, known as Underhill, where Chesil Beach connects the island to the mainland. Adjoining Fortuneswell are Chiswell to the west and Castletown to the north. Fortuneswell occupies the steeper land above sea level, whereas Chiswell and Castletown occupy flat land close to sea level, next to Chesil Beach and Portland Harbour respectively. Fortuneswell has a main shopping street, and along with Easton, is the main hub of the island's activities. Local restaurants include Miss Piggy’s Pantry, Daniels, Cafe India, and The Cove House Inn.

The center of Fortuneswell ( which is at is longitude -2°26'34.900 and latitude 50°33'35.215 ) is located 1 mile away from Portland, 4 miles away from Lansdowne, 4 miles away from Weymouth and 6 miles away from Chickerell.

Available Fortuneswell lodging

We currently have 7 accommodations in and around Fortuneswell.

Fortuneswell Hotels, B&Bs and Guest Houses

Hotels

Ashmira Hotel

Approx 5 miles away in Weymouth:

The Ashmira hotel is a large Victorian House situated on the Jurassic Coast in Weymouth, Dorset.

3 Westerhall Road

Weymouth, Dorset

Bed & Breakfasts

Turnstones Luxury B&B

Turnstones is an elegant Victorian house with every amenity, providing first class, comfortable, and relaxing bed and breakfast accomodation, whether you're visiting Dorset's beautiful Jurassic coast for business or pleasure.

6 Ventnor Road

Fortuneswell, Dorset

Hotels

Best Western Hotel Prince Regent

★★★★★★

Approx 5 miles away in Weymouth:

This Grade II listed seafront hotel set on Weymouth Georgian Esplanade with magnificent views of the bay and coastline. The town centre and harbour are a short level stroll away. Ideal for exploring Dorset's countryside, history and attractions.

"Property is showing its age a little. No car parking and downtown Weymouth is terrible for parking anyway. Room was large and had a good view of the beach. All over an ok stay, but could probably do ..... "

139 The Esplanade

Weymouth, Dorset

Alendale

Guest House

Approx 5 miles away in Weymouth:

The Alendale Guest House - a warm and comfortable Grade 2 listed Georgian building found in the beautiful seaside holiday town of Weymouth, Dorset. The guest house offers comfortable accommodation on a B&B basis, all rooms have en-suite .....

4 Waterloo Place

Weymouth, Dorset

Fortuneswell Camping, Caravans, Self Catering

Photograph of Pebble Bank Caravan Park, Weymouth

Listing updated 2026

Cottage / Caravan Parks

Pebble Bank Caravan Park

Approx 4 miles away in Weymouth:

Pebble Bank Caravan Park is situated less than two miles from Weymouth town centre, and its Blue Flag Award beach. We are close to the coastal footpath, on the heritage coast, and the famous Chesil Beach which runs from Portland to Abbotsbury, in .....

90 Camp Road

Weymouth, Dorset

Holiday Parks

Littlesea Holiday Park

Approx 4 miles away in Weymouth:

A superb 5-Star holiday village as awarded by the English Tourist Council, central to Dorset’s Jurassic Coastline, Littlesea has recently been substantially developed to become a leading Haven Park.

Lynch Lane

Weymouth, Dorset

Cottage / Caravan Parks

Castle Cove Caravans

Approx 4 miles away in Weymouth:

17a Trinity Road

Weymouth, Dorset

Booking.com

Things to see and do, places to eat in Fortuneswell

Crab House Cafe

Crab House Cafe ( Dining / Seafood ). We are situated in a breathtaking part of Dorset, looking out over Chesil beach. We have our own Portland Oyster beds just a stones throw from the restaurant so you can enjoy fresh Oysters on your table within minutes of them leaving the water! www.crabhousecafe.co.uk Link

The Boat That Rocks ( Dining / Pizza ). We are a marina-side restaurant and bar, just a 5-minute walk away from the Weymouth and Portland National Sailing Academy with plenty of outdoor seating and fantastic views across the harbour- perfect for relaxing with a drink whilst keeping an eye on the sailing action. www.tbtr.co.uk Link