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Spring Afternoon Tea in a Dorset Holiday Cottage for May Half Term
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May Half Term Holiday Cottages

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Which Trusted Trader

Celebrate the arrival of early summer with a May half term break in Dorset. Our selection of holiday homes provides the perfect home base for exploring the county’s breathtaking landscapes, from the rolling hills of the countryside to the dramatic cliffs of the Jurassic Coast. Whether you’re seeking adventure or relaxation, Dorset has something for everyone, making it the ideal destination for your May half term holiday in the UK.

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{{ pagination.totalResults }}37 properties found
Hill View image [alt]
Hill View
Weymouth
5/5
4
2
1
1
1 night fromNone available
3 nights fromNone available
7 nights from £1,007.65
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Littlecot image [alt]
Littlecot
Weymouth
5/5
8
4
2
2
1 night fromNone available
3 nights from £1,434.96
7 nights from £1,958.30
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Aerial shot of Swanage self-catering cottage with nearby beach and town [alt]
Billet Doux
Swanage
5/5
2
1
1
1
1 night fromNone available
3 nights fromNone available
7 nights from £929.10
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Wisteria Cottage image [alt]
Wisteria Cottage
Dorchester
5/5
4
2
1
0
5 nights from £1,105.00
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St Marks Cottage image [alt]
St Marks Cottage
Swanage
5/5
4
2
2
0
1 night from £833.00
3 nights from £833.00
7 nights from £1,135.75
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3 Puddledock Cottage image [alt]
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
6
3
1
0
1 night fromNone available
3 nights fromNone available
7 nights from £1,339.45
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Leap House image [alt]
Leap House
Wareham
5/5
4
3
1
0
1 night fromNone available
3 nights fromNone available
7 nights from £1,001.35
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Underhill image [alt]
Underhill
Nr Corfe Castle
5/5
7
4
3
3
1 night from £1,017.09
3 nights fromNone available
7 nights fromNone available
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Poppy Cottage image [alt]
Poppy Cottage
Dorchester
5/5
4
2
1
1
1 night fromNone available
3 nights fromNone available
7 nights from £1,552.50
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Front view of Silvermere luxury lakeside cottage, Overton Island [alt]
Silvermere
Silverlake
5/5
12
4
4
0
1 night fromNone available
3 nights from £2,707.50
7 nights fromNone available
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Bluebell Cottage image [alt]
Bluebell Cottage
Dorchester
5/5
3
2
1
1
1 night fromNone available
3 nights fromNone available
7 nights from £1,000.00
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Greenhayes cottage exterior, Langton Matravers [alt]
Greenhayes
Langton Matravers
4.8/5
4
2
1
2
1 night fromNone available
3 nights fromNone available
7 nights from £1,135.75
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Froxfield Cottage image [alt]
Froxfield Cottage
Langton Matravers
4.9/5
6
3
2
1
1 night fromNone available
3 nights fromNone available
7 nights from £1,219.75
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Mimosa House image [alt]
Mimosa House
Sandford, Wareham
5/5
4
2
1
0
1 night fromNone available
3 nights fromNone available
7 nights from £952.00
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Beachway House holiday home aerial or exterior view [alt]
Beachway House
Weymouth
5/5
12
6
5
2
1 night fromNone available
3 nights fromNone available
7 nights from £3,105.00
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Dorset Farmhouse image [alt]
Dorset Farmhouse
Portesham, Nr Abbotsbury
4.9/5
6
3
2
0
1 night fromNone available
3 nights fromNone available
7 nights from £1,382.50
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big cottage in swanage exterior and gardens [alt]
Lizards Rest
Swanage
4.7/5
9
4
2
0
1 night from £542.20
3 nights fromNone available
7 nights fromNone available
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Thistledown image [alt]
Thistledown
Dorchester
5/5
2
1
1
1
2 nights from £621.00
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Elizabeth Cottage image [alt]
Elizabeth Cottage
Lulworth Cove,
5/5
4
2
2
1
1 night fromNone available
3 nights fromNone available
7 nights from £1,114.75
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1 Westport Cottage Ph3 Web [alt]
Westport Cottage
Wareham
4.9/5
5
3
2
0
1 night fromNone available
3 nights fromNone available
7 nights from £1,173.55
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Olive Cottage image [alt]
Olive Cottage
Swanage
5/5
4
2
1
0
1 night from £380.33
3 nights fromNone available
7 nights fromNone available
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Cosy lounge interior of Stonehaven holiday rental [alt]
Stonehaven
Silverlake
5/5
8
4
3
0
1 night fromNone available
3 nights fromNone available
7 nights from £1,949.25
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Owl Cottage image [alt]
Owl Cottage
Wareham
5/5
4
2
1
1
1 night fromNone available
3 nights fromNone available
7 nights from £1,115.50
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The Lookout image [alt]
The Lookout
Silverlake
5/5
10
4
4
0
1 night fromNone available
3 nights from £2,669.60
7 nights fromNone available
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Enjoy

May half term family holidays

Make the most of your time spent with your family with a stay in one of our well-appointed holiday cottages for May half term. Dorset offers a wealth of family-friendly activities. Sandy beaches and coastal walks to fascinating historical sites and charming market towns. Our cottages are designed with families in mind.  They offer spacious living areas, comfortable bedrooms, and all the amenities you need for a stress-free holiday. Whether you’re planning a week-long stay or a shorter break, our May half term family-friendly cottages ensure everyone enjoys a memorable holiday.

Indulge in a

Luxury cottage for May half term

Add a touch of luxury to your May half term break by choosing one of our cottages with hot tubs. After a day spent exploring Dorset’s beautiful countryside, there’s nothing better than relaxing in the warm bubbles of a private hot tub. Our luxury cottages combine modern comforts with picturesque settings.  They are the perfect choice for those who want to unwind and indulge during their holiday in May.

Pet-friendly

Self-catering for May half term

Our dog-friendly cottages for May half term welcome pets.  They offer easy access to dog-friendly beaches, walking trails, and open spaces where your pets can roam freely.  Most of the beaches in Dorset are still open to pets in May.  So its the ideal time to plan your getaway.

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