Photo by Marilyn Peddle

Shillingstone Vacation Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Shillingstone holiday rentals

Interior
Apple Tree Cottage

Cottage in Blandford Forum

Apple Tree Cottage
3.0 star property
9.0 out of 10, Wonderful, (2)
"Nice 300 year old cottage in the countryside. Modern kitchen and extension also nice. Small garden suitable for a dog. Owners were responsive to questions."
United Kingdom
Daniel
The price is RM1,944
RM2,332 total
includes taxes & fees
29 Dec - 30 Dec
Apple Tree Cottage
3 bedrooms, individually decorated, individually furnished, desk
Holiday Home With Hot Tub & Sauna

Holiday Home in Bournemouth

Holiday Home With Hot Tub & Sauna
4.0 star property
9.0 out of 10, Wonderful, (4)
" What the full holiday with my kids thanks guys"
United Kingdom
Ayhan
The price is RM755
RM1,893 total
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home With Hot Tub & Sauna
Private kitchen
Way's Forge

Cottage in Dorchester

Way's Forge
3.0 star property
10.0 out of 10, Exceptional, (3)
"Way's Forge is a quirky, convenient accommodation for exploring a wide variety of locations in the area and further afield. . It was a very comfortable stay and we enjoyed it very much. "
United Kingdom
Virginia
The price is RM2,355
RM2,826 total
includes taxes & fees
4 Jan - 5 Jan 2026
Way's Forge
Dining
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

Residence in Dorchester

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
2.0 star property
The price is RM3,356
RM4,682 total
includes taxes & fees
24 Dec - 25 Dec
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
Exterior
Pamper House Holiday Home And Annex

Holiday Home in Ferndown

Pamper House Holiday Home And Annex
3.0 star property
Pamper House Holiday Home And Annex
Interior
Meadow View Barn

Cottage in Wareham

Meadow View Barn
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great little place, perfect for my stay. Nice and clean, all amenities and good communication from the owner."
United Kingdom
Mitch
The price is RM2,184
RM2,620 total
includes taxes & fees
5 Jan - 6 Jan 2026
Meadow View Barn
Interior
Tom's Barn

Cottage in Yeovil

Tom's Barn
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is RM1,864
RM2,236 total
includes taxes & fees
29 Dec - 30 Dec
Tom's Barn
Exterior
Rowdens Barn

Cottage in Blandford Forum

Rowdens Barn
3.5 star property
10.0 out of 10, Exceptional, (2)
"Lovely countryside location. "
Canada
Michael
The price is RM1,729
RM2,075 total
includes taxes & fees
2 Jan - 3 Jan 2026
Rowdens Barn
Outdoor dining
New Barn

Cottage in Blandford Forum

New Barn
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is RM1,817
RM2,181 total
includes taxes & fees
28 Dec - 29 Dec
New Barn
Property grounds
Shippon Barn

Cottage in Yeovil

Shippon Barn
3.5 star property
10.0 out of 10, Exceptional, (1)
"Lovely accommodation with everything you could want. Very helpful owner. Will certainly stay again when we are in the area"
United Kingdom
Peter
The price is RM1,659
RM1,991 total
includes taxes & fees
2 Jan - 3 Jan 2026
Shippon Barn
Interior
The Cottage

Cottage in Wimborne

The Cottage
3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful cottage, really huge lounge and lots of fields around. Host Dawn was super helpful and the cottage had everything you needed. The showers were great and super clean, I always found that the pictures always look better than the actual place when you arrive, but this was even better in person. This is our first time renting a cottage rather than a hotel, and we're taking our puppy. We will be back with the whole family this time to enjoy it again."
United Kingdom
manjit
The price is RM2,032
RM2,439 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Cottage
Interior
The Old Cart Shed

Cottage in Fordingbridge

The Old Cart Shed
3.0 star property
10.0 out of 10, Exceptional, (1)
"Fantastic location for a 60th birthday celibration. Extremely well equipped kitchen, 3 bedrooms. Quiet rural location, near the New Forest "
United Kingdom
Keith
The price is RM2,819
RM3,382 total
includes taxes & fees
28 Dec - 29 Dec
The Old Cart Shed
Interior
Oke Apple Cottage

Cottage in Blandford Forum

Oke Apple Cottage
3.0 star property
10.0 out of 10, Exceptional, (3)
"Location ideal "
United Kingdom
Nazir
The price is RM1,307
RM1,569 total
includes taxes & fees
6 Jan - 7 Jan 2026
Oke Apple Cottage
Property grounds
The Folly at Castlebridge

Cottage in Warminster

The Folly at Castlebridge
3.5 star property
10.0 out of 10, Exceptional, (1)
"Séjour merveilleux, un trésor caché dans la campagne Anglaise. Des hôtes généreux et de bons conseils sur les visites à faire dans les environs "
France
Christophe
The price is RM2,480
RM2,975 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Folly at Castlebridge
Outdoor dining
Grist Mill Cottage

Cottage in Shaftesbury

Grist Mill Cottage
3.0 star property
10.0 out of 10, Exceptional, (1)
"Private drive and entrance made it very private. Whole cottage really nicely equipped. Plus everything made very easy and welcoming."
United Kingdom
Anonymous traveller
Grist Mill Cottage
Front of property
Brook Cottage

Cottage in Gillingham

Brook Cottage
3.0 star property
8.0 out of 10, Very good, (1)
"Was comfortable and safe"
United Kingdom
Catherine
The price is RM1,414
RM1,697 total
includes taxes & fees
6 Jan - 7 Jan 2026
Brook Cottage
Interior
The Studio

Cottage in Shaftesbury

The Studio
3.0 star property
10.0 out of 10, Exceptional, (3)
"Comfortable, clean with great proximity to North Dorset. Lots of local walks and villages to discover. Highly recommend. "
United Kingdom
Lindsey
The price is RM1,645
RM1,974 total
includes taxes & fees
27 Dec - 28 Dec
The Studio
Interior
East Lodge

Cottage in Fordingbridge

East Lodge
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is RM2,346
RM2,815 total
includes taxes & fees
19 Jan - 20 Jan 2026
East Lodge
Interior
Pound Cottage

Cottage in Dorchester

Pound Cottage
3.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely peaceful place "
United Kingdom
Enid
The price is RM1,548
RM1,858 total
includes taxes & fees
8 Jan - 9 Jan 2026
Pound Cottage
Living room
Little Willow

Cottage in Blandford Forum

Little Willow
3.5 star property
8.0 out of 10, Very good, (1)
"Not sure what the last question meant? The garden or Dorset. Both lovely."
United Kingdom
John
The price is RM1,618
RM1,942 total
includes taxes & fees
5 Jan - 6 Jan 2026
Little Willow
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shillingstone Hotel Reviews

Holiday Inn Express Poole by IHG

Holiday Inn Express Poole by IHG

10/10 Excellent
"Clean room, friendly staff, comfy bed and excellent breakfast."
Martin 1-night trip
Posted 2 days ago
Holiday Inn Express Poole by IHG

Find out more about Shillingstone

Search for holiday rentals in Shillingstone on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Shillingstone using one of the methods below:

  • View our selection of featured holiday rentals in Shillingstone
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Look no further and take a look at our great range of rental properties in Shillingstone!

Frequently asked questions

Are there holiday rentals in Shillingstone?

Yes, there are holiday rentals close to the most popular sights in Shillingstone, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Shillingstone has to offer?

Blue Vista: This holiday home rental outside Shillingstone is located near the beach, and has a fireplace, a garden and free WiFi to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

What can I see and do in Shillingstone?

Cultural attractions include Shillingstone Railway Project, whereas Dorset Area of Outstanding Natural Beauty is a spot to enjoy nature. In the wider area, you’ll find Gold Hill Museum and Larmer Tree Gardens.

What are holiday rentals like in Shillingstone?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shillingstone. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for families.