Secure your stay for £20 T&Cs apply

Chiswell On Portland Holiday Cottages

360 properties found

An outdoor area with a house and kayaks by the water at Still Waters in Weymouth

Still Waters

Weymouth, Dorset

7 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£1008

A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth

Plain Sailing

Weymouth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£719

An outdoor entrance with opened doors leading to a room at The Orchard in Ringstead
Offer

The Orchard

Ringstead, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£595

The front entrance of a house with a green door and a window beside it with plants in black pots on a paved area at Sea Gem in Castletown Portland

Sea Gem

Castletown, Portland, Dorset

7 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£948

A house with windows and a pathway at 1 Fernhill Avenue Weymouth

Greenwell

Weymouth, Dorset

8 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£988

A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth

Portside

Greenhill Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£559

Rose Cottage

Rose Cottage

Osmington, Dorset

6 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£727

Two beige houses with black doors and windows on a paved street at Jurassic Coast House in Portland

Jurassic Coast House

Portland, Dorset

8 Guests
4 Beds
Pet Friendly
Wifi

for 7 nights

From

£998

A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz

Blueberry Cottage

Sutton Poyntz, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£392

A balcony with a round glass table and wicker chairs overlooking a marina and trees at Sunset View in Castletown Portland

Sunset View

Castletown, Portland, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£508

Front view of a stone cottage with white framed windows and door at Alpen Rose Cottage Easton Portland

Alpen Rose Cottage

Easton Portland, Dorset

5 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£617

A house with a driveway and garden at Tudor Rose in Weymouth

Tudor Rose

Weymouth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£694

An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour

George's House

Brewers Quay Harbour, Dorset

7 Guests
4 Beds
Pet Friendly
Wifi

for 7 nights

From

£851

A white building with a stone wall and flowers in front and a lighthouse behind at Old Higher Lighthouse Stopes Cottage in Portland Bill

Portland Bill, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£648

An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze

Sea Spray

Bowleaze, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£554

A stone and blue wooden building with external staircases and balconies under a clear sky at Santiago House in Weymouth

Santiago House

Weymouth, Dorset

8 Guests
4 Beds
No pets
Wifi

for 7 nights

From

£1235

Exterior view of a white house with flower pots near the door and a tree in the foreground at The Little Cottage in Weymouth

The Little Cottage

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£571

The exterior of a white terraced house with blue doors and window sills at South Harbour Cottage in Weymouth

South Harbour Cottage

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£592

A living room with a staircase and a sofa at Harbourside in Weymouth

Harbourside

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£438

A house with outdoor seating area at Budmouth Upwey near Weymouth

Budmouth

Upwey near Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£604

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.