Summer Breaks in Dorset

Your search returned 530 cottages.

Sort by Most relevant

Most relevant
Price (lowest first)
Price (highest first)
Sleeps (lowest first)
Sleeps (highest first)
Rating (lowest first)
Rating (highest first)
Location (A to Z)
Location (Z to A)
Property name (A to Z)
Property name (Z to A)

Show 10

Map View

59
Baytree Lodge Save
Osmington, Dorset
- Sleeps12
- Bedrooms5
- Pet FriendlyYes
- Dream Cottages rating
Luxurious 5 star contemporary property. (Ref. 993982)
Pets go free
Wi-fi
Off-road parking
Swimming pool
Dishwasher
Washing machine
Baby-friendly
Games room
€5168 off - Mon 28th Dec 2026 to 4th Jan 2027
7 nights from Sat 5th Jun From €4780

Last booked yesterday
Book now
42
6 The Terrace Save
Brewers Quay Harbour, Dorset
- Sleeps4
- Bedrooms2
- Pet FriendlyYes
- Dream Cottages rating
A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. (Ref. 1096352)
Pets go free
Wi-fi
Dishwasher
Washing machine
Baby-friendly
7 nights from Sat 5th Jun From €1406

Book now
24
Shepherd's Barn Save
Between Milborne St Andrew and Winterborne Whitechurch, Dorset
- Sleeps6
- Bedrooms3
- Pet FriendlyYes
- Dream Cottages rating
A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)
Pets go free
Wi-fi
Off-road parking
Electric car charging
Ground floor bedroom
Dishwasher
Washing machine
Baby-friendly
7 nights from Fri 11th Jun From €1607

Book now
42
Corner Barn Save
Winterborne Stickland, Dorset
- Sleeps4
- Bedrooms2
- Pet FriendlyYes
- Dream Cottages rating
Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. (Ref. 19285)
Pets go free
Wi-fi
Off-road parking
Electric car charging
Ground floor bedroom
Dishwasher
Washing machine
Baby-friendly
Games room
7 nights from Fri 4th Jun From €983

Book now
27
Coastguard View Save
Portland Bill, Dorset
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
- Dream Cottages rating
Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. (Ref. 1169819)
Wi-fi
Off-road parking
Ground floor bedroom
Dishwasher
Washing machine
7 nights from Sat 5th Jun From €898

Book now
38
Lookout Save
Cove Castle, Dorset
- Sleeps4
- Bedrooms2
- Pet FriendlyYes
- Dream Cottages rating
Comfortable Spanish style holiday home in Weymouth. (Ref. 994352)
Pets go free
Wi-fi
Off-road parking
Dishwasher
Washing machine
7 nights from Fri 20th Aug From €1404

Book now
16
Harbourside Haven Penthouse 2 Save
Weymouth, Dorset
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
- Dream Cottages rating
A marvellous third-floor penthouse situated overlooking the harbour in Weymouth, Dorset. (Ref. 1059267)
Wi-fi
Dishwasher
Washing machine
Baby-friendly
7 nights from Fri 4th Jun From €1061

Book now
37
The Old Cart Shed Save
Winterborne Stickland, Dorset
- Sleeps6
- Bedrooms3
- Pet FriendlyYes
- Dream Cottages rating
Exceptional, spacious rural barn conversion. (Ref. 905897)
Pets go free
Wi-fi
Off-road parking
Electric car charging
Ground floor bedroom
Dishwasher
Washing machine
Baby-friendly
Games room
7 nights from Fri 4th Jun From €1076

Book now
21
4 Duck Street Save
Cerne Abbas, Dorset
- Sleeps5
- Bedrooms3
- Pet FriendlyYes
- Dream Cottages rating
4 Duck Street, a welcoming pet-friendly cottage resting in the village of Cerne Abbas, Dorset, boasts an enclosed garden and village amenities close by. (Ref. 1090492)
Pet friendly (extra charges may apply)
Wi-fi
Dishwasher
Washing machine
Baby-friendly
Sky TV
7 nights from Sat 5th Jun From €998

Book now
51
Mallows Byre Save
Yetminster, Dorset
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
- Dream Cottages rating
Mallows Byre is a delightful barn conversion situated in the historic village of Yetminster in Dorset with an outstanding freestanding bath and Smart TV. (Ref. 955342)
Wi-fi
Ground floor bedroom
Dishwasher
Washing machine
7 nights from Fri 4th Jun From €920

Book now