Secure your stay for £20 T&Cs apply

Chiswell On Portland Holiday Cottages

360 properties found

An outdoor patio with furniture and plants at Flat 1, 2 Wooperton Street Weymouth
Offer
New

The Secret Courtyard

Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£569

The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth

Seasides

Weymouth, Dorset

13 Guests
6 Beds
No pets
Wifi

for 7 nights

From

£2111

A brick house with a black front door and three windows with gravel and plants in the front garden at The Pines in Weymouth
Offer

The Pines

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£703

Quay Cottage

Quay Cottage

Weymouth, Dorset

5 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£590

A row of multi-colored buildings along a waterfront with a boat named Top Cat III docked at Safe Harbour Brewers Quay harbour

Safe Harbour

Brewers Quay harbour, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£1010

The front view of a two-story brick house with a green door and multiple windows and a paved driveway at Bridge Apartment in Weymouth

Bridge Apartment

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£457

A balcony with two chairs and a table overlooking a rocky shoreline and the sea at Sunset Lodge in Fortuneswell

Sunset Lodge

Fortuneswell, Dorset

6 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£623

A living room with a sofa and a coffee table at Vista Mare 3 in Weymouth

Vista Mare 3

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£1160

A garden with tables and chairs at Beck House in Weymouth
Offer

Beck House

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£444

A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour

Tradewinds

Brewers Quay Harbour, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£734

A kitchen with white cabinets marble countertops skylights and floral curtains at Upsidedown House Brewers Quay Harbour
Offer

Upsidedown House

Brewers Quay Harbour, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£963

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

Old Boathouse

Weymouth, Dorset

5 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£623

A balcony with a table and chairs overlooking a garden and sea at The View in Weymouth

The View

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£681

Two small wooden huts with open doors on grass surrounded by trees and two wooden chairs with a tree stump table at Sika in Warmwell

Sika

Warmwell, Dorset

2 Guests
1 Beds
No pets

for 7 nights

From

£371

A building with apartments and boats at Harbourside Apartment Weymouth

Harbourside Apartment

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£644

A dining table with flowers butter croissants orange juice and jam by windows overlooking a beach at Grandview in Weymouth

Grandview

Weymouth, Dorset

6 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£911

Exterior view of a white townhouse with blue doors and railings and stone columns at Hops House in Brewers Quay Harbour

Hops House

Brewers Quay Harbour, Dorset

6 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£761

An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth

Townbridge Apartment

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£643

A beach and ocean view with a clock tower in Weymouth

Vista Mare 1

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£1172

A house with a brick exterior and driveway at The Chocolate Box in Weymouth

The Chocolate Box

Weymouth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

for 7 nights

From

£875

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.