Home | News | Cosy Holiday Retreats in Poole this Winter

Summer’s over, and winter’s knocking on our doors, but that doesn’t mean you have to say goodbye to holidays for another year!

This is the perfect time to cosy up in a charming holiday cottage in Poole. Picture a warm fireplace crackling away, a mug of hot chocolate ripe for the sipping, and the knowledge that you’ve left all of your wintry worries behind. 

Holidays in Poole aren’t just reserved for summery beach getaways: join us as we explore some of the cosiest winter holiday retreats Poole has to offer this season. Get ready to embrace the chilly weather in style and create unforgettable memories in the heart of Dorset’s coastal beauty. 

Let’s explore the best of these holiday cottages in Poole that promise to make your winter escape truly magical!

Lobster Cottage

Cosy Self-catering Cottage in Poole for 6 People

Lobster Cottage is a charming, character-filled cottage with three cosy bedrooms and fantastic views of Poole Harbour. It’s nestled just a short walk from Poole Quay, where you’ll find an array of restaurants and bars. Inside the cottage, you’ll find an inviting living room complete with a 40-inch smart TV with freeview, Netflix, and Disney – even an Xbox One to keep you entertained when the weather gets the best of you!

In the open-plan kitchen, you’ll find modern amenities, including a dishwasher, electric induction hob, electric fan oven and a microwave. A washer/dryer combo is available in the cloakroom for your convenience.

Head upstairs to discover the master bedroom with a luxurious king size bed and stunning corner views of the harbour. It comes with a modern ensuite shower room that includes a walk-in shower. The second bedroom features another king size bed, and the third bedroom is furnished with two singles, plus a large family bathroom.

Book your stay in this cosy holiday cottage in Poole.


Cosy Self-Catering Holiday in Poole for 4 People

Located in the heart of Poole’s Georgian Old Town, Chimneys is only a few minutes’ walk from Poole Quay and the harbourside, where views extend out to Brownsea Island. This holiday cottage boasts both a garden and a double garage, as well as a cosy conservatory. 

The beautifully finished living room features an electric fireplace, perfect for keeping you warm on your winter holiday in Poole without having to worry about logs and kindling. The cottage is fully kitted out with a Smart TV in the lounge and modern amenities including a double oven, slimline dishwasher, microwave and washing machine in the kitchen. 

Upstairs, you’ll find the master bedroom which features a super king size bed that can be split into two twins upon request, as well as an extra pull-out single bed. The second bedroom also has two twins which can be joined together to create a double, making this a particularly family-friendly cottage in Poole. 

Book your stay in this cosy holiday cottage in Poole.

Lulworth House

Large, Dog-friendly Holiday Cottage in Poole for 7 People

This spacious holiday accommodation near Poole is located in Hamworthy, just moments away from gorgeous beach walks and Poole Harbour. It’s the perfect choice for unforgettable family vacations, offering a range of features to enhance your stay including a hot tub, a games room, a treadmill and a trampoline.

As you step inside the house, you’ll be greeted by an inviting open-plan living and dining area, complete with a Smart TV and a modern log burner. The adjacent conservatory or snug area is an ideal spot to relax, with additional seating and children’s toys. The kitchen features a breakfast area and another Smart TV, plus integrated appliances including a microwave, coffee machine, wine fridge, and dishwasher. 

Upstairs, you’ll find four well-appointed bedrooms to ensure a restful night’s sleep. The master bedroom boasts a luxurious super king size bed with a comfortable memory foam mattress and a fitted wardrobe. The second bedroom features a double bed, a smart TV, and even a cosy window seat – the perfect reading nook. The third bedroom features a roomy king size bed and patio-style windows, and the fourth is equipped with a single day bed and a pull-out single trundle bed. 

Book your stay in this dog-friendly home in Poole.

Candle Island View

Cosy Holiday Townhouse in Poole for 6 People

This stylish, contemporary, dog-friendly holiday accommodation near Poole Quay offers the perfect base from which to enjoy views out across the harbour. The delightful location is home to a diverse selection of restaurants and bars, all within a leisurely stroll. The house is a haven for both you and your furry companions, offering captivating views from every floor, a charming balcony, and a cosy courtyard garden for your four-legged friends to enjoy.

Upon entering, you’ll step into a welcoming hallway leading to an open-plan kitchen and dining area. Sliding doors grant access to the courtyard garden and unveil sweeping panoramas that include the bustling Fisherman’s port and Brownsea Island. The kitchen is fully equipped complete with an electric hob, oven, fridge/freezer, dishwasher and a microwave. A convenient cloakroom and access to a utility area in the garage housing a washer/dryer round out the practical features.

Climbing the stairs to the first floor, you’ll find a spacious living room with full-width windows that provide an ever-changing harbour view – perfect for watching the world go by. The second bedroom on this level offers a comfortable double bed and fitted wardrobes as well as a family bathroom. The second floor houses the king size master bedroom with an ensuite shower room as well as a twin bedroom. 

Book your stay in this stylish holiday home in Poole.


Dog-friendly Holiday Cottage in Poole for 4 People

Escape to Gulliver’s, a charming 2-bedroom cottage that warmly welcomes both you and your dogs for an unforgettable winter retreat. The snug hideaway is nestled in the heart of nature, just a short stroll through woodland paths to Canford Cliffs, Evening Hill and Lilliput. The fantastic blue-flag (and dog-friendly) beaches of Sandbanks are a mere 5-minute drive away, offering you and your pup the perfect setting for brisk winter walks. 

The cosy living room is complete with a charming feature fireplace and a Smart TV with Freeview. The real treat is located in the kitchen – an Aga provides both heat and the means to delicious, slow cooked meals. The kitchen also boasts modern amenities including a dishwasher, fridge/freezer, microwave, washing machine, a separate dryer – and a large walk-in larder. The adjoining conservatory serves as the perfect dining area, with doors opening to the patio, letting in the crisp winter light. For added convenience, a separate shower room is located on the ground floor – ideal for those with limited mobility. 

Head upstairs to find the master king size bedroom, offering glimpses of the sea, and an ensuite bathroom. The second bedroom – also with an ensuite – features two single beds which can be zipped and linked to form a super king size double. The enclosed garden offers the perfect space for your dogs to enjoy – provided they don’t mind the cold!

Book your stay in this dog-friendly cottage in Poole.

The Coach House

Self-catering Holiday Apartment in Bournemouth for 6 People

The Coach House is a delightful two-bedroom maisonette, perfect for a cosy winter break. The well-maintained apartment is conveniently situated just a five minute stroll from Westbourne, where you’ll find an array of fantastic restaurants, cafes and boutiques to explore. Inside the stylish maisonette you’ll find an open-plan living area, with dining space and a fully equipped kitchen featuring a fridge freezer, dishwasher, electric oven, induction hob, microwave, coffee machine, washing machine, and tumble dryer. 

The living room features comfy sofas to curl up on after a day out in the cold – one of them can be transformed into a sofa bed upon request, accommodating two additional guests. A Smart TV with freeview will keep you entertained.

Upstairs, there are two bedrooms and two bathrooms. The master bedroom offers a king size bed and an ensuite bathroom. The second bedroom features dual aspect windows and the flexibility of either a zip and link king size bed or two single beds. Outside you’ll find a private decking area with a fire pit, set against a wintry backdrop of pine trees. 

Book your stay in this beautiful apartment in Bournemouth this winter.


Stylish Holiday Townhouse in Poole for 6 People

This delightful three storey, three bedroom, two bathroom townhouse is nestled in the heart of Ashley Cross. The surrounding area is vibrant and diverse – this cosy holiday home offers you quick access to a multitude of superb restaurants and bars. 

As you step inside this charming townhouse, you’re greeted by an inviting entrance hall leading to an open-plan living and dining area, as well as a fully equipped kitchen. The sliding doors open to a small courtyard garden, perfect for savouring the crisp winter air. The kitchen boasts modern amenities, including a gas hob and extractor, a gas double oven, a spacious American double full-height fridge/freezer with an ice machine, a wine fridge, a dishwasher, a microwave, and a convenient washing machine. 

Head up the stairs to the first floor and discover the master bedroom, featuring a luxurious super king size bed. An additional bedroom on this floor is furnished with two single beds. On the top floor, you’ll find a double bedroom with a standard double bed and a charming corner window. 

Book your next holiday in Poole.

The Willows

Secluded Holiday Cottage in Christchurch for 6 People

This unique cottage is located near the historic town of Christchurch, which offers a multitude of attractions, from its natural harbour to the historic Priory and Highcliffe Castle. 

The Willows, a charming old railway cottage dating back to 1925, is chock full of character and period features. Inside, the living room welcomes you with the warmth of a beautiful log burner that also gently heats the adjoining entrance hall. The spacious country kitchen has a large, round table, perfect to enjoy a nice roast dinner after a winter’s walk.

Venture upstairs to discover three bedrooms, each graced with lovely views of the adjacent fields and a wall-mounted flat-screen television. The master bedroom has a king size bed and access to a balcony area with seating for two and gorgeous countryside views. Two additional double bedrooms provide ample space for guests. The family bathroom features a luxurious roll-top bath – the perfect addition to this wonderful cottage. 

Book this historic holiday cottage in Christchurch.

Looking for a cosy cottage in Poole for your next family holiday? We hope you’ll love these holiday cottages in Dorset just as much as we do, and we’re here to help you with your holiday every step of the way. 

Our range of self-catering holiday properties in Christchurch, Poole and Bournemouth are each beautifully unique – whatever you’re looking for, we’re passionate about finding the perfect holiday property for you. From quaint cottages for small families to spacious, modern five-bedroom houses, we’re proud to offer a true home-from-home experience on Dorset’s stunning Jurassic Coast.

Browse our range of self-catering properties or get in touch with us to get started.

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