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Cosy escapes

Winter Breaks

As frost delicately coats the Dorset countryside, the verdant leaves of meandering hedgerows are replaced with clusters of ruby-red berries, luscious holly, and winter-blooming flowers. The rugged coastline, usually bustling with summer visitors, is now a little quieter. And as you stroll along the coast path with your family or dog in tow, the rhythmic crashing of waves against the chalk-faced cliffs is a reminder of your welcomed winter escape after a long autumn stuck in the office. The sun doesn’t have to be at its warmest for our coastal county to be enjoyed. Browse our selection of winter holiday lets in Dorset for a festive short break to brighten those darker days.

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Billet Doux
Swanage
5/5
2
1
1
1
Set on a quiet, private road in a peaceful part of Swanage, Billet Doux is a beautifully presented ground-floor retreat. It is ideal for couples or solo travellers looking to slow down and enjoy a more relaxed pace of life.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
1 night from £307.50
3 nights from £344.88
7 nights from £848.25
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Owls Roost
Ringstead Bay
5/5
2
1
1
0
Luxury couples' retreat near Ringstead Bay with a super-king bedroom, freestanding bath, peaceful estate gardens and Jurassic Coast walks nearby.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
BBQ
BBQ
Walk to Pub
Walk to Pub
Coffee Machine
Coffee Machine
1 night from £376.00
3 nights from £423.25
7 nights from £580.00
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Dorset Farmhouse
Portesham, Nr Abbotsbury
4.9/5
6
3
2
0
The Dorset Farmhouse offers a tranquil setting with glorious country views and only 3 miles from Chesil Beach.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Walk to Pub
Walk to Pub
Bathroom Towels
Bathroom Towels
Bed Linen Is Provided
Bed Linen Is Provided
1 night from £426.30
3 nights from £447.72
7 nights from £605.50
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Allington Barn
Nr Blandford Forum
5/5
18
7
6
0
Set quietly within the rolling countryside of North Dorset, Allington Barn is a place designed for gathering - where long tables fill with food and conversation, where mornings begin slowly with coffee on the terrace, and evenings stretch into laughter
Hot Tub
Hot Tub
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
1 night fromNone available
3 nights from £3,323.25
7 nights from £7,717.32 £6,978.82
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Malvern Apartment
Swanage
4.5/5
2
1
1
0
A spacious Edwardian apartment for two, just a short walk from Swanage Beach, with period charm and a glimpse of the bay.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
1 night fromNone available
3 nights from £333.17
7 nights from £458.45
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Private hot tub. Outdoor Pool Timeslot
The Bothy
Minterne Magna
5/5
6
3
3
2
A boutique estate retreat with a private hot tub, exclusive daily pool access and peaceful walled garden setting.
Hot Tub
Hot Tub
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
1 night from £915.00
3 nights from £1,103.50
7 nights from £1,510.00
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Hill View
Weymouth
4.9/5
4
2
1
1
Set in the peaceful Weymouth suburb of Preston, Hill View offers a delightful retreat for couples or small families.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
1 night from £359.75
3 nights from £362.73
7 nights from £488.40
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Pool and Tennis Court Access
Pool House
Minterne Magna
5/5
2
1
1
2
Romantic countryside escape for two with exclusive evening pool access, a wood burner and beautiful estate surroundings.
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
BBQ
BBQ
1 night from £450.00
3 nights from £461.50
7 nights from £630.00
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Saxon Mews
Wareham
5/5
4
2
2
0
Saxon Mews is a modern and comfortable two-bedroom home that offers the perfect blend of convenience and style
Allocated Parking
Allocated Parking
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Near Supermarket
Near Supermarket
1 night from £464.75
3 nights from £471.58
7 nights from £627.50
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Sandy Shores Apartment
Swanage
5/5
5
2
1
0
Just a two-minute stroll from the golden sands of Swanage Beach, Sandy Shores is a welcoming second floor apartment offering the perfect coastal base for couples, friends, or families.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
1 night from £328.46
3 nights from £328.46
7 nights from £483.40
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Leap House
Wareham
5/5
4
3
1
0
Leap House is a well-presented three-bedroom semi-detached holiday retreat, sitting peacefully within a short walk of Wareham Quay. This well-presented holiday accommodation, is an excellent base to explore one of England’s Saxon Walled towns and nearby beaches of the Jurassic
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Public transport travel
Public transport travel
1 night fromNone available
3 nights from £482.60
7 nights from £606.00
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Orchid House
Langton Matravers
4.9/5
8
4
3
2
A delightful big cottage in Purbeck, set right on the doorstep of Dorset’s most breath-taking coastal walks, in the village of Langton Matravers.
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
1 night fromNone available
3 nights from £580.00
7 nights from £742.00
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Harbour Vista
Weymouth
5/5
4
2
2
0
Set within a striking Grade II listed building on Weymouth’s historic harbour, Harbour Vista is a stylish third-floor apartment offering a front-row seat to one of Dorset’s most vibrant seaside towns.
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
1 night from £547.25
3 nights from £547.56
7 nights from £735.50
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Willow Cottage
Weymouth
5/5
2
1
1
2
Romantic retreat for two with a private wood-fired hot tub, sunny courtyard and easy access to Dorset's coast.
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
1 night fromNone available
3 nights from £405.00
7 nights from £945.00
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Owl Cottage
Wareham
5/5
4
2
1
1
A quaint stone cottage in the heart of Wareham. Beautifully decorated throughout.
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
1 night from £575.00
3 nights from £575.00
7 nights from £580.00
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Heathlands
Studland
4.7/5
6
3
1
0
A welcoming family cottage just 200 yards from Studland Beach, with coastal walks, village pubs and the Jurassic Coast on your doorstep.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
Bathroom Towels
Bathroom Towels
1 night from £527.50
3 nights from £527.50
7 nights from £610.75
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Daisy’s
Swanage
4.7/5
6
3
3
1
Stylishly decorated 3 bedroom holiday home in Swanage. Daisy's offers everything you need for a relaxing break, from comfortable bedrooms with ensuite for each room to a private bubbling hot tub, perfect for unwinding after a long day exploring the
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
1 night from £475.00
3 nights from £475.00
7 nights from £616.00
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Stone Quay Cottage
Swanage
4.9/5
3
2
1
2
Stone Quay Cottage is right in the heart of the beautiful old fishing town of Swanage, just a stones throw away from the historic Stone Quay, the lovely sandy beaches, the Victorian Pier and all the amenities. This two bedroom
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
1 night fromNone available
3 nights from £413.55
7 nights from £909.95
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Walk to beach
Beachway House
Weymouth
5/5
12
6
5
2
A six bedroom, six bathroom family home just 300 yards from Weymouth beach with parking.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
1 night from £1,075.00
3 nights from £1,075.00
7 nights from £1,640.00
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Sea Reach
Swanage
4.9/5
4
2
1
0
2 Bedrooms. We are delighted to introduce Sea Reach, this spacious and modern ground floor apartment is in a prime place to stay in Swanage, just 3/4 minutes’ walk from the beach.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
1 night fromNone available
3 nights from £391.09
7 nights from £527.25
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View of Corfe Castle
Castle View House
Corfe Castle
5/5
9
5
4
1
Escape the ordinary at Castle View House, a haven in the countryside that accommodates up to nine guests. With its enchanting views of Corfe Castle, stylish open-plan interiors, and dog-friendly atmosphere, this residence promises a unique and memorable retreat. Nestled
Secure Garden (pets)
Secure Garden (pets)
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
EV Charge Point
EV Charge Point
Ground Floor Bedroom
Ground Floor Bedroom
1 night fromNone available
3 nights from £1,477.50
7 nights from £1,492.50
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Sea Tower
Weymouth
4.9/5
6
3
2
0
Breathtaking luxury holiday home which is yards from Weymouth beach. Sea Tower has wide ranging coastal views and an exquisite interior for a luxury break.
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
EV Charge Point
EV Charge Point
Near Supermarket
Near Supermarket
Balcony
Balcony
1 night from £754.81
3 nights from £754.81
7 nights from £819.70
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The Old Butcher’s Cottage
Corfe Castle
4.8/5
6
3
2
2
The Old Butcher’s Cottage is bursting with character. Recently renovated throughout, this high spec property is the hideaway you’ve been searching for. Luxurious furnishings and exquisite linens adorn the bedrooms, living area and kitchen, providing stunning accommodation that the whole
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
1 night fromNone available
3 nights from £503.00
7 nights from £600.00
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The Lookout
Silverlake
5/5
10
4
4
0
An exceptional and unique luxury lakeside home. Thoughtfully designed with style, comfort, and indulgence in mind, The Lookout is a modern lakeside home set within the award-winning Silverlake Estate near Dorchester. Every element of this contemporary four-bedroom property has been
Hot Tub
Hot Tub
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
EV Charge Point
EV Charge Point
1 night from £1,686.50
3 nights from £1,686.50
7 nights from £1,701.50
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winter dog walk
Bring your companion

Pet-friendly winter holiday lets in Dorset

Your pets are an important part of your festive activities and for those seeking to share a winter short break in Dorset with their four-legged friend, our selection of dog-friendly holiday cottages in Dorset ensures no family member is left behind. Picture wandering through the frost-dusted hills of Purbeck with your faithful dog bounding happily beside you. Alternatively, imagine enjoying a brisk walk along one of our deserted beaches; the salty breeze kisses your cheeks as your dog runs in and out of the lapping waves.  Many of our cosy cottages and coastal retreats warmly welcome pets, with amenities and spacious surroundings tailored to ensure a comfortable stay for both you and your dog.

christmas tree at holiday home ready for a festive short break
Getaway to the countryside

FESTIVE SEASON BREAKS

Nestled between rolling hills and weathered coastline, the county of Dorset beckons tourists with an abundance of seasonal offerings. As you walk through one of our quaint market towns, the scent of mulled wine wafts through the frost-kissed air and the cosy pub offers warm refuge from the winter chill, its crackling hearths inviting guests to unwind with a mug of steaming hot chocolate.

For those who wish to venture into the countryside, whimsical landscapes unfold like scenes from a storybook, revealing hidden valleys and ancient woodlands waiting to be explored. Clifftops adorned with seasonal greenery and their calm sandy beaches below also provide an enticing backdrop for leisurely strolls with the entire family. Whether you’re heading out of the city for a short coastal stay or looking for a holiday cottage to spend time with your loved ones during the festive season, we can help you find a perfect winter let in Dorset.

bike on a summer evening
Cosyup this winter

Romantic winter short breaks in Dorset

The crisp winter air carries the faint scent of wood smoke from distant cottages and the desire to curl up in front of a cosy wood burner is very, very tempting. As the daylight fades and the evenings become shorter, our idyllic Dorset holiday cottages are the perfect backdrop for couples to snuggle close and share quiet conversations over a glass of fine, artisan wine. Our selection of winter short breaks in Dorset offers postcard-perfect retreats and boutique hideaways for stolen kisses and shared memories this festive season. Walk hand-in-hand through streets studded with Christmas lights or enjoy a locally made, candle-lit dinner in a charming restaurant nearby. Dorset sets the stage for an unforgettable romantic escape during these colder months and our variety of smaller cottages and winter lets perfect for couples are the perfect place to stay.