Winter Retreats

We have some gorgeous properties ideal for a winter retreat in Dorset with cosy living rooms boasting open fires, central heating and woodburning stoves. What's better than coming back from a bracing walk to a warm and welcoming cottage giving you a home from home holiday. See our properties below that could provide you with a quick winter getaway to recharge the batteries


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107 Properties found
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Weymouth, West Dorset

WY437

(No dates selected)

£345 - £755
per week
From £259 for a 3-night stay
  • 4 Star Gold
  • 3 By the Sea is a newly renovated first floor apartment, located in one of the character buildings just a few steps away from Weymouth’s famous beach, an excellent town base with all the local amenities on the doorstep. This lovely one bed apartment which is arranged over two floors, offering everything you need to enjoy your stay.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • On-street parking
  • Parking permit provided
  • Beach 0.1 miles
  • Pub 0.1 miles

Swanage, Dorset

WY440

(No dates selected)

£444 - £943
per week
From £333 for a 3-night stay
  • 4 Star Gold
  • As the name suggests it previously formed part of St. Marks Primary School; this substantial Victorian building dating back to 1855 was recently converted as part of a prestigious development along with 3 other cottages. Finished to a very high standard throughout, this spacious property has been sympathetically transformed incorporating contemporary modern design alongside original features including vaulted high ceiling and stunning tall windows.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 2 Bathrooms
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Beach 1 mile
  • Pub 0.2 miles

Swanage, Dorset

WY441

(No dates selected)

£310 - £635
per week
From £233 for a 3-night stay
  • 3 Star
  • Dating back to the 19th Century, this beautiful traditional Purbeck stone cottage is thought to originally  be a quarryman’s cottage. The cottage is packed with original period features, none more so than in the spacious living room with stone walls, beautiful beams, flag stone flooring and large inglenook fire place with working log burner.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Private parking
  • Open fire or woodburner
  • Beach 1 mile
  • Pub 0.3 miles

Swanage, Dorset

WY372

(No dates selected)

£325 - £685
per week
From £244 for a 3-night stay
  • 3 Star
  • Originally built around the 1900s as a private house, the Monte Rosa then became a hotel in 1966 and subsequently over the years this was then converted into apartments. Middle Sea comes with direct beach access and is situated on the first floor of this well maintained apartment block, enjoying stunning views across the sea and out towards Ballard Down and the Isle of Wight.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • Garden
  • Private parking
  • Pub 0.1 miles

Swanage, Dorset

WY357

(No dates selected)

£383 - £617
per week
From £287 for a 3-night stay
  • 4 Star
  • This beautiful ground floor one bedroom Victorian apartment offers style, comfort and space in abundance. With its own private entrance and spacious hallway, Nestleton has been finished to a very high standard and is just a couple of minutes' walk down a hill into the town centre and sandy beach making it a fabulous retreat for couples.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • On-street parking
  • Open fire or woodburner
  • Beach 0.2 miles
  • Pub 0.1 miles

Swanage, Dorset

WY413

(No dates selected)

£299 - £573
per week
From £224 for a 3-night stay
  • 3 Star
  • A lovely, traditional, Purbeck stone terrace cottage Grade II listed, in the old part of town, just a five minute walk into the town and the beach.  Perfect for a couple looking to explore the Purbecks, or just relax on the beach!
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • Enclosed garden
  • On-street parking

Swanage, Dorset

WY428

(No dates selected)

£305 - £605
per week
From £229 for a 3-night stay
  • 3 Star Gold
  • Corbeau House was originally a large Victorian Villa and has been sympathetically renovated to create 5 stylish separate apartments. Original features help create a sense of space and charm, including high ceilings, sash bay windows and brick exposed walls. Externally the property has also been equally well renovated blending both local materials with original mosaic tiled entrance hall, large doorway and Purbeck Stone front wall.
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • On-street parking
  • Beach 0.3 miles
  • Pub 0.3 miles

The Annex

WY380

Weymouth, Dorset

WY455

(No dates selected)

£299 - £525
per week
From £224 for a 3-night stay
  • 3 Star Gold
  • BumbleBees is a delightful, beautifully refurbished one bedroom annexe located in Weymouth. It is perfectly located for couples looking to explore the historic Jurassic coast, the vibrant seaside town of Weymouth or even take in the scenery on local cycle routes. 
  • 2 Guests
  • 1 Bedroom
  • No Pets
  • 1 Bathroom
  • WiFi
  • Enclosed garden
  • Private parking
  • Beach 2 miles
  • Pub 1 mile

Swanage, Dorset

WY389

(No dates selected)

£350 - £796
per week
From £263 for a 3-night stay
  • 3 Star Gold
  • Speedwell is a delightful 1830’s stone workers cottage, quietly tucked away in the centre of town, and within easy walking distance to the beach.  Set over three floors, Speedwell is brimming with character, has a sea view from the top floor bedroom, and a pretty courtyard to the rear of the property.
  • 3 Guests
  • 2 Bedrooms
  • No Pets
  • 1 Bathroom
  • WiFi
  • Garden
  • On-street parking
  • Open fire or woodburner
  • Beach 0.1 miles
  • Pub 0.1 miles

Swanage, Dorset

WY411

(No dates selected)

£387 - £780
per week
From £290 for a 3-night stay
  • 4 Star
  • Centrally located in the seaside town of Swanage and perfect for couples
  • 3 Guests
  • 2 Bedrooms
  • No Pets
  • 1 Bathroom
  • WiFi
  • Private parking
  • Beach 0.1 miles
  • Pub 0.1 miles

Swanage, Dorset

WY382

(No dates selected)

£404 - £918
per week
From £303 for a 3-night stay
  • 3 Star Gold
  • Situated in one of the oldest parts of Swanage, this delightful Grade II listed former quarryman's cottage dates back to 1804. Over the years the cottage has been beautifully modernised and refurbished without losing any of its charm.
  • 3 Guests
  • 2 Bedrooms
  • 1 Pet
  • 1 Bathroom
  • WiFi
  • Garden
  • Enclosed garden
  • Open fire or woodburner
  • Beach 1 mile
  • Pub 0.1 miles
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