Secure your stay for £20 T&Cs apply

Winter Short Breaks in Dorset

474 properties found

A cottage with a thatched roof and a garden at Happiness Cottage in Piddlehinton
Offer

Happiness Cottage

Piddlehinton, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Sat 28th Nov for 3 nights

£483

Terraced houses with bay windows and colored doors on a street at 26 High West in Weymouth

26 High West

Weymouth, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Sat 28th Nov for 3 nights

£397

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

Sat 28th Nov for 3 nights

£787

A garden with red roses and a metal chair beside a brick house at The Corner House in Weymouth

The Corner House

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

Tue 1st Dec for 3 nights

£581

Three modern two story houses with green window frames and stone wall facades with a paved driveway and some plants at Pebbles Reach in Fortuneswell

Pebbles Reach

Fortuneswell, Dorset

7 Guests
3 Beds
Pet Friendly
Wifi

Mon 4th Jan for 3 nights

£680

A house with a garden and pathway at 29 Bincleaves Road Weymouth
New

Coast Path Cottage

Weymouth, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

Tue 1st Dec for 3 nights

£796

A house with a garden and greenhouse at Tokenhill Cottage Piddletrenthide

Tokenhill Cottage

Piddletrenthide, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

Sat 28th Nov for 3 nights

£806

A garden with a hot tub and dining table at Mallow Cottage in Langton Matravers

Mallow Cottage

Langton Matravers, Dorset

7 Guests
3 Beds
Pet Friendly
Wifi

Sat 28th Nov for 3 nights

£651

A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour

Firkin Cottage

Brewers Quay Harbour, Dorset

6 Guests
4 Beds
No pets
Wifi

Mon 4th Jan for 3 nights

£507

A driveway with a silver van parked next to a house with a garage and trees at Redcliff View Lodge in Weymouth

Redcliff View Lodge

Weymouth, Dorset

6 Guests
3 Beds
No pets
Wifi

Mon 4th Jan for 3 nights

£638

A cream colored two story house with blue window frames and a blue front door at Fisherman's Cottage King Street in Fortuneswell

Fisherman's Cottage, King Street

Fortuneswell, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Mon 4th Jan for 3 nights

£470

Stone terraced houses with red doors and red leafy trees behind wooden fences

Sea Breeze

Swanage, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Mon 30th Nov for 3 nights

£441

Exterior view of a row of houses with bay windows a blue door and a plant in a pot at The Shambles in Fortuneswell

The Shambles

Fortuneswell, Dorset

4 Guests
2 Beds
No pets
Wifi

Sun 3rd Jan for 3 nights

£600

A modern building with balconies and stairs at Seafern House 36B in Poole

Sea Fern House - 36B

Poole, Dorset

6 Guests
3 Beds
No pets
Wifi

Sun 3rd Jan for 3 nights

£802

A living room with a sofa and television at 2Bed Ringwood Cabin incl Park Pass SelfCheckin Saint Leonards near Ferndown
New

Saint Leonards near Ferndown, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Sat 28th Nov for 3 nights

£505

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

Mon 4th Jan for 3 nights

£800

A semi detached house with a driveway and potted plants at The Anchorage in Bournemouth

The Anchorage

Bournemouth, Dorset

6 Guests
2 Beds
Pet Friendly
Wifi

Sat 9th Jan for 3 nights

£599

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

Mon 4th Jan for 3 nights

£590

Stone cottages with white doors and windows and a red mailbox at Higgledy Piggledy Cottage in Swanage

Higgledy Piggledy Cottage

Swanage, Dorset

5 Guests
3 Beds
Pet Friendly
Wifi

Mon 25th Jan for 3 nights

£522

Two triangular wooden cabins with stairs surrounded by trees and grass at Rose Lodge in Milton on Stour

Rose Lodge

Milton on Stour, Dorset

6 Guests
3 Beds
Pet Friendly
Wifi

Sat 28th Nov for 3 nights

£443

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.