Secure your stay for £20 T&Cs apply

Chiswell On Portland Holiday Cottages

360 properties found

A garden with grass and flowerbeds in front of a blue bungalow with a veranda and outdoor chairs at Harbour View Bungalow in Weymouth

Harbour View Bungalow

Weymouth, Dorset

6 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£1080

A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth

New Boathouse

Weymouth, Dorset

7 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£837

A stone house with windows and a garden with bushes in front at Anchor Cottage in Weston Portland

Anchor Cottage

Weston, Portland, Dorset

5 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£515

Front of a thatched cottage with green door flowers and stone wall at Cajun Cottage in West Lulworth

Cajun Cottage

West Lulworth, Dorset

5 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£774

A living room with sofas a patterned rug a TV and a fireplace at Brewers House in Weymouth

Brewers House

Weymouth, Dorset

7 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£849

A dining area with round wooden table and chairs next to sliding glass doors leading outside with sofas and kitchen stools in Mermaid Cottage in Wakeham Portland

Mermaid Cottage

Wakeham, Portland, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£573

A large apartment building with green-tinted glass balconies and cylindrical glass elevator shafts along a street at Manhattan Beach in Castletown Portland

Manhattan Beach

Castletown, Portland, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£587

A blue painted two storey building with bay windows and white doors with black railings in front at Harbour Watch Apartment 1 Brewers Quay Harbour

Harbour Watch Apartment 1

Brewers Quay Harbour, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£610

A living room with sofas a coffee table a fireplace a television and wall art at Victorian Town House in Weymouth

Victorian Town House

Weymouth, Dorset

8 Guests
5 Beds
Pet Friendly
Wifi

for 7 nights

From

£692

A living room with a sea view at Portland View in Portland Bill

Portland View

Portland Bill, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£517

A view of the beach and sea with boats anchored offshore and greenery in the foreground at Castle Cove Cottage in Weymouth

Castle Cove Cottage

Weymouth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£787

A two story detached house with bay windows and a central front door with plants on each side at Family House in Weymouth

Family House

Weymouth, Dorset

12 Guests
6 Beds
No pets
Wifi

for 7 nights

From

£1271

A stone cottage with a thatched roof and a wooden table and benches outside at Magnolia Cottage Osmington

Magnolia Cottage Osmington

Osmington, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£608

A brick exterior with white doors windows hanging plants and a sculpture at Barley Mews Brewers Quay Harbour

Barley Mews

Brewers Quay Harbour, Dorset

9 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£1210

Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington

Laurel Cottage

Osmington, Dorset

3 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£494

A living room with a brown sectional sofa armchair and round coffee table near a sliding door at Waterston Cottage in West Lulworth

Waterston Cottage

West Lulworth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£871

An outdoor area with a wooden building and gravel pathway at Dirdale in Weymouth

Dirdale

Weymouth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£740

A stone cottage with a thatched roof and garden by the roadside at Badgers Cottage in Langton Herring near Chickerell

Badgers Cottage

Langton Herring near Chickerell, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£512

A row of brick houses with blue and turquoise front doors and white windows on a street at Chapelhay Cottage in Weymouth

Chapelhay Cottage

Weymouth, Dorset

5 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£627

The Old Post Office

The Old Post Office

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£517

Manage Your Cookie Preferences

We use cookies to enhance your browsing experience, analyse our traffic, personalise content and for marketing purposes including the personalisation of ads on the internet. We also set cookies that are necessary for our website to work. You can accept, decline, or manage your cookie preferences by clicking the appropriate button. More information about Google ads can be found in our cookie policy.