Photo by Marilyn Peddle

Shillingstone Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Shillingstone holiday rentals

Apple Tree Cottage

Apple Tree Cottage
3.0 star property
Blandford Forum
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 NZ$984
includes taxes & fees
2 Jan - 3 Jan 2026
Apple Tree Cottage

Holiday Home With Hot Tub & Sauna

Holiday Home With Hot Tub & Sauna
4.0 star property
Bournemouth
9.0 out of 10, Wonderful, (4)
" What the full holiday with my kids thanks guys"
United Kingdom
Ayhan
The price is NZ$790
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home With Hot Tub & Sauna

Rowdens Barn

Rowdens Barn
3.5 star property
Blandford Forum
10.0 out of 10, Exceptional, (2)
"Lovely countryside location. "
Canada
Michael
The price is NZ$881
includes taxes & fees
2 Jan - 3 Jan 2026
Rowdens Barn

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
2.0 star property
Dorchester
The price is NZ$1,943
includes taxes & fees
6 Jan - 7 Jan 2026
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

Pamper House Holiday Home And Annex

Pamper House Holiday Home And Annex
3.0 star property
Ferndown
Pamper House Holiday Home And Annex

Tom's Barn

Tom's Barn
3.5 star property
Yeovil
10.0 out of 10, Exceptional, (1)
The price is NZ$949
includes taxes & fees
2 Jan - 3 Jan 2026
Tom's Barn

The Cottage

The Cottage
3.0 star property
Wimborne
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 NZ$1,048
includes taxes & fees
8 Jan - 9 Jan 2026
The Cottage

Shippon Barn

Shippon Barn
3.5 star property
Yeovil
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 NZ$840
includes taxes & fees
2 Jan - 3 Jan 2026
Shippon Barn

Way's Forge

Way's Forge
3.0 star property
Dorchester
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 NZ$1,199
includes taxes & fees
8 Jan - 9 Jan 2026
Way's Forge

New Barn

New Barn
3.5 star property
Blandford Forum
10.0 out of 10, Exceptional, (1)
The price is NZ$925
includes taxes & fees
3 Jan - 4 Jan 2026
New Barn

Oke Apple Cottage

Oke Apple Cottage
3.0 star property
Blandford Forum
10.0 out of 10, Exceptional, (3)
"Location ideal "
United Kingdom
Nazir
The price is NZ$665
includes taxes & fees
8 Jan - 9 Jan 2026
Oke Apple Cottage

Meadow View Barn

Meadow View Barn
3.0 star property
Wareham
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 NZ$1,111
includes taxes & fees
7 Jan - 8 Jan 2026
Meadow View Barn

Grist Mill Cottage

Grist Mill Cottage
3.0 star property
Shaftesbury
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
The price is NZ$819
includes taxes & fees
2 Jan - 3 Jan 2026
Grist Mill Cottage

Pound Cottage

Pound Cottage
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (2)
"Lovely peaceful place "
United Kingdom
Enid
The price is NZ$788
includes taxes & fees
8 Jan - 9 Jan 2026
Pound Cottage

Brook Cottage

Brook Cottage
3.0 star property
Gillingham
8.0 out of 10, Very good, (1)
"Was comfortable and safe"
United Kingdom
Catherine
The price is NZ$720
includes taxes & fees
7 Jan - 8 Jan 2026
Brook Cottage

Flat 4 - Hengistdury

Flat 4 - Hengistdury
3.0 star property
Bournemouth City Centre
The price is NZ$760
includes taxes & fees
3 Jan - 4 Jan 2026
Flat 4 - Hengistdury

The Mews Cottage

The Mews Cottage
3.5 star property
Salisbury
9.0 out of 10, Wonderful, (2)
"A very cosy, comfortable and well equipped cottage. Extremely convenient for the high street and the station. We were visiting for a family event in Tisbury and it made the perfect base for the weekend. We would like to have stayed longer - maybe next time!"
United Kingdom
Caroline
The price is NZ$1,162
includes taxes & fees
30 Dec - 31 Dec
The Mews Cottage

Little Willow

Little Willow
3.5 star property
Blandford Forum
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 NZ$823
includes taxes & fees
8 Jan - 9 Jan 2026
Little Willow

Pond View

Pond View
3.0 star property
Fordingbridge
The price is NZ$927
includes taxes & fees
14 Jan - 15 Jan 2026
Pond View

The Folly at Castlebridge

The Folly at Castlebridge
3.5 star property
Warminster
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 NZ$1,256
includes taxes & fees
2 Jan - 3 Jan 2026
The Folly at Castlebridge
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shillingstone Hotel Reviews

Find out more about Shillingstone

Everything you need to know about Shillingstone holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shillingstone holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shillingstone holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shillingstone holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shillingstone. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shillingstone holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shillingstone holiday rentals we have selected for you start as low as NZ$251 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shillingstone rentals

At Expedia, we put the best Shillingstone holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shillingstone rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shillingstone holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shillingstone. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.