The Half Term in October is very popular with those who still want a sunny holiday but who prefer a quieter, laid back time of year.  September and October is a time for those who enjoy the warmth of a stroll through autumnal woodland but who also enjoy cuddling up in front of an open fire in the evening.

You can book some exceptional properties, but book early as we are always fully booked for this week. Dorset attractions will still be open and of course you can still enjoy the countryside, we are the only county without a motorway and  the coastline boasts World Heritage Site Status with over 40 beaches to enjoy.   A wealth of attractions run special events over the half term holidays, including the The Sealife Centre, Monkey World and Kingston Lacey. Popular activities include Dorset walks, photography, cycling, sailing and horseriding on the beach. Take time to enjoy some local fayre in some of the best pubs and restaurants to be found.

Filter & Sort
{{ pagination.totalResults }}0 properties found
Forest Edge
Sandford
4.8/5
Forest Edge is a two bedroom semi-detached chalet bungalow offering luxury accommodation near Wareham. Mainly laid out on the ground floor, this delightful holiday home has been completely refurbished to a very high standard.
4
2
2
2
26th October - 2nd November  £736.75
19th October - 2nd November  £1,423.50
19th - 26th October  £736.75
View & Book
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.
6
3
2
0
19th - 26th October  £894.25
26th October - 2nd November  £894.25
19th October - 2nd November  £1,738.50
View & Book
Seaspray
Swanage
5/5
Located steps away from the sandy beach and traditional promenade in Swanage, Seaspray is a three-bedroom, 1930s-style apartment with panoramic sea views. Situated on the wonderful seafront parade, this town centre location is perfect for families or friends seeking a relaxing coastal escape within a stone’s throw of many of Dorset’s prolific attractions.
5
3
2
0
18th - 25th October  £831.25
View & Book
The Aspens
Swanage
4.8/5
Delightful light-filled family holiday home, situated just a stone’s throw from beautiful Swanage Pier.
5
2
2
0
18th - 25th October  £694.75
18th October - 1st November  £1,339.50
25th October - 2nd November  £778.50
+1 more stays
View & Book
Below Decks
Swanage
4.8/5
Below Decks is a gorgeous, seafront holiday home that sleeps 6 guests. Situated on the Parade in the heart of Swanage with the main beach, restaurants and shops directly on your doorstep, it is perfect for a relaxing coastal getaway.
6
3
2
2
19th - 26th October  £936.25
19th October - 2nd November  £1,822.50
26th October - 2nd November  £936.25
View & Book
Brook Cottage
Corfe Castle
4.8/5
Step back in time and enjoy this delightful semi-detached cottage, exuding charm and character throughout. Built in the early 1730s, this distinctive Grade II red bricked cottage, is set in the heart of the historic village of Corfe Castle. This cosy retreat, nestled in the heart of the Purbecks, would surely be able to tell a tale or two! Sitting peacefully at the bottom of the romantic Castle ruins, you will enjoy morning coffee with arguably one of the most impressive backdrops in Dorset.
6
3
3
0
25th October - 1st November  £1,219.75
25th October - 2nd November  £1,348.50
18th - 25th October  £1,219.75
+1 more stays
View & Book
The Lawns
Charlton Marshall
4.8/5
2 bedroom holiday cottage near to Blandford in the pretty village of Charlton Marshall, lovely country views and walks. Property all on one level with stunning garden.
4
2
1
2
26th October - 2nd November  £689.50
19th October - 2nd November  £1,329.00
19th - 26th October  £689.50
View & Book
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.
2
1
1
0
19th - 26th October  £500.50
19th October - 2nd November  £951.00
26th October - 2nd November  £500.50
View & Book
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.
4
2
1
0
26th October - 2nd November  £710.50
19th - 26th October  £710.50
19th October - 2nd November  £1,371.00
View & Book
Westport Cottage
Wareham
4.9/5
3 bedrooms. A distinctive period holiday cottage to rent in Wareham, in a unique location with tastefully presented interior. This is one of only three cottages built on top of the old Saxon walls in Wareham.
5
3
2
0
18th - 25th October  £857.50
18th October - 1st November  £1,665.00
25th October - 2nd November  £951.75
+1 more stays
View & Book
Angel Cottage
Swanage
4.7/5
Nothing is more refreshing than a coastal holiday near the sea and if you’re looking for a cosy, quaint cottage, Angel Cottage should be first on your wishlist. This mid terrace cottage is the perfect base to discover miles of heritage coastline or relax and unwind on the blue flag sandy beach
2
1
1
2
18th - 21st October  £363.10
31st October - 2nd November  £389.92
24th October - 2nd November  £677.50
+101 more stays
View & Book
Balcony Apartment
Swanage
5/5
2 Bedrooms. Fabulous seaside apartment in Swanage. Stunning views from the balcony across the bay to the Isle of Wight. This spacious and comfortable property is equipped with all you might need for a family get away.
4
2
1
0
26th October - 2nd November  £784.00
19th October - 2nd November  £1,518.00
19th - 26th October  £784.00
View & Book