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Cosy escapes

Winter Breaks

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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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2018 Front PHOTO Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange Self Catering Accommodation In Swanage Rear To House Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange image Newton Manor Grange Self Catering Accommodation In Swanage Garden Newton Manor Grange Self Catering Accommodation In Swanage Outlook To Sea Newton Manor Grange image
Newton Manor Grange
Swanage
4.6/5
3 bedrooms. This beautiful four star holiday home is the ideal choice for a self catering holiday in Swanage. This home boasts large picture windows and is an unusual upside down house that takes full advantage of the views, across the seaside town of Swanage to the sea and the Isle of White beyond. WIFI.
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2nd - 5th November  £434.42
4th - 6th November  £434.42
4th - 7th November  £434.42
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IMG 7696 Daisy’s image Daisy’s image Daisy S Holiday Home In Swanage Kitchen Daisy’s image Daisy’s image IMG 7637 IMG 6520 IMG 7760 1 Daisy’s image Daisy’s image Daisy’s image Daisy’s image P1281534 Daisy’s image Daisy’s image Daisy’s image Daisy’s image Daisy’s image
Daisy’s
Swanage
4.7/5
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 coast!
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3
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2nd - 5th November  £434.42
6th - 8th November  £434.42
5th - 7th November  £434.42
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Tilshead image Tilshead Five Star Luxury Accommodation For Large Parties External View Thumbnail Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image Tilshead image
Tilshead
Langton Matravers
4.8/5
4 Bedroom, 3 bathrooms. Stunning countryside views with sea glimpses. Tilshead is a beautifully designed home nestled within the lovely village of Langton Matravers. This exceptional, bespoke house was created to offer a practical yet luxurious, contemporary residence complete with large relaxing garden. Graded four star gold by Visit England, this luxury Dorset holiday cottage is ideal for large parties or families.
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4th - 7th November  £797.00 £690.24
3rd - 7th November  £908.81 £785.96
4th - 6th November  £797.00 £690.24
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Gable Cottage image IMG 9452 HDR IMG 9455 HDR Gable Cottage image Gable Cottage image Gable Cottage image IMG 9464 HDR IMG 9479 HDR Edit IMG 9482 HDR Edit IMG 9485 HDR Gable Cottage image IMG 9476 HDR Gable Cottage image IMG 9458 HDR Gable Cottage image IMG 9503 HDR Edit IMG 9512 HDR Gable Cottage image Gable Cottage image Gable Cottage image
Gable Cottage
Corfe Castle
4.8/5
3 bedrooms. Located on a large corner plot, this light and airy family holiday home in Corfe Castle, offers comfortable furnishings and modern fittings. Conveniently situated close to the common and village amenities including the bakery, general store, tea rooms and pubs.
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1st - 4th November  £510.85 £506.50
4th - 7th November  £510.85 £506.50
3rd - 5th November  £510.85 £506.50
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Flat 3 4 Cranborne Rd Ph2 Web Flat 3 4 Cranborne Rd Ph5 Web Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image Beach Approach image
Beach Approach
Swanage
4.8/5
Settle into a lovely family holiday at Beach Approach. A two bedroom ground floor apartment. A flat walk will take you to Swanage beach and High Street, which is lined with cute cafés, boutiques, and fine restaurants. Beach Approach is perfect for families with top sights in easy reach: Swanage Railway is just a two minute stroll away; take a trip down memory lane on the vintage steam engine to the historic village of Corfe Castle.
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3rd - 6th November  £360.75 £343.75
3rd - 7th November  £406.12 £372.52
3rd - 8th November  £488.00 £448.00
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Wye Knot
Swanage
4.8/5
A delightful ground floor apartment with private garden is perfectly placed for a family's getaway, within easy access to Swanage beach and town attractions.
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4th - 7th November  £457.41
4th - 6th November  £457.41
2nd - 4th November  £457.41
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Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image Honeysuckle Cottage image
Honeysuckle Cottage
Kingston, Nr Corfe Castle
4.8/5
This two-bedroom + annex Purbeck stone cottage is tucked away in the very quiet village of Kingston, near Corfe Castle. Escape the everyday, with luxury interiors and enhancing views! Pet-friendly.
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3
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1st - 8th November  £857.50
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Cherry Lodge image
Cherry Lodge
Wareham
0/5
Comfort and space to be enjoyed by friends and family in this large, modern home complete with bubbling hot tub. Its pet friendly and has plenty of parking. The quality of this home and the size of the garden are what attracts guests to Cherry Lodge.
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5th - 8th November  £514.90
1st - 8th November  £697.00 £637.00
2nd - 8th November  £700.00
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Seacombe Ph40 Web Seacombe image Seacombe Ph37 Web Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe Ph43 Web Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image Seacombe image
Seacombe
Langton Matravers
4.9/5
Nestled in the sleepy village of Langton Matravers proudly stands Seacombe, an exquisite 4 bedroom family home. This stunning link detached home could easily be the set to a photoshoot for Country Living magazine. Furnished with high quality new furniture, sumptuous duck down quilts, crisp white linen and beds so comfortable you will struggle to leave them, Seacombe is the holiday home you've been searching for. ?
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2nd - 5th November  £764.01
2nd - 7th November  £1,041.25
2nd - 6th November  £870.85
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Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image IMG 4787 IMG 4747 Edit IMG 4778 Pano Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image Froxfield Cottage image
Froxfield Cottage
Langton Matravers
4.9/5
3 Bedrooms. Froxfield Cottage is a cosy renovated quarryman’s cottage built in the 1850’s, sympathetically decorated in a mix of contemporary and traditional style.
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3rd - 7th November  £623.50 £527.50
2nd - 7th November  £746.00 £616.00
1st - 3rd November  £552.00 £527.50
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IMG 5608 HDR Edit Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image IMG 5644 HDR Malvern Apartment image Malvern Apartment image Malvern Apartment image Malvern Apartment image
Malvern Apartment
Swanage
4.5/5
This appealing large, ground floor apartment is part of a modern conversion of a former Edwardian hotel, right in the heart of the seaside town of Swanage in a quiet residential, tree lined street, less than 5 mins walk to restaurants, pubs, shops and the beach. You can enjoy a lovely glimpse view across Swanage bay from the lounge bay window.
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5th - 8th November  £338.60
1st - 3rd November  £353.94
3rd - 5th November  £338.60
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Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image Church Cottage image
Church Cottage
Corfe Castle
4.7/5
Set in an idyllic location, this welcoming 18th century, Grade II listed character cottage stands in the heart of the picturesque village of Corfe Castle. Church Cottage boasts a beautiful garden and welcomes two dogs, making it an ideal base for a family get together.
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4th - 8th November  £511.80 £475.00
3rd - 7th November  £511.80 £475.00
4th - 6th November  £475.00
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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.

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