Woolland Vacation Rentals from $156: Search Short-Term Rentals

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Our top choices for Woolland vacation rentals

A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

1. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

$194 nightly

Oct 10 - Oct 11

Total with taxes and fees

A house with a tiled roof, a front door with glass panels, and a gravel driveway.

2. Oke Apple Cottage

Blandford Forum

Nazir

$317 nightly

Oct 30 - Oct 31

Total with taxes and fees

A compact living space with a kitchenette, a dining area, and a sofa.

3. The Orchid

Gillingham

Suzanne B.

$118 nightly

Oct 11 - Oct 12

Total with taxes and fees

A two-story building with a blue storefront labeled "The Dorsel Store."

4. A spacious, well equipped private annexe with garden and parking in Shaftesbury.

Shaftesbury Dorset

Martin K.

$156 nightly

Oct 11 - Oct 12

Total with taxes and fees

A modern outdoor patio with wicker furniture and a glass door leading to a covered area.

5. Private Luxury By The Sea

Poole

Luke

$194 nightly

Oct 21 - Oct 22

Total with taxes and fees

A beach with a natural rock arch formation.

6. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Wool

Kristina

$363 nightly

Oct 11 - Oct 12

Total with taxes and fees

A modern living room with a grey sofa, yellow cushions, a pink throw, and a dining area in the background.

7. Beautiful NEW 3 bedroom house - garden & parking

Poole

Lee

$223 nightly

Oct 10 - Oct 11

Total with taxes and fees

A modern bedroom with a large bed, a glass bedside table, and a view of the outdoors.

8. Luxurious Glass House with Private Hot tub

Blandford Forum

$169 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern living room with a sofa, coffee table, and a kitchen area with a washing machine.

9. Streamside Apartments

Yeovil

Anonymous traveler

$133 nightly

Oct 22 - Oct 23

Total with taxes and fees

A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

10. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

Winterborne Whitechurch

"Excellent cottage! Super quirky and perfect for a large group. My husband’s family all met at the Langham vineyard (jut 8 minute’s drive up the road from the accommodation) to celebrate his 50th ; adults, kids, dog…we had a wonderful time and carried on the celebrations with an evening of chat in the comfortable lounge and some food in the spacious dining area before heading to bed (all 10 of us). Martin was a wonderful host, very quick responses and super accommodating. The whole area is...

Stacia B.

$497 nightly

Nov 3 - Nov 4

Total with taxes and fees

A modern living room with a grey sofa, yellow cushions, a yellow rug, and a large window with curtains.

11. Brand NEW 3 bedroom house - garden & parking +wifi

Poole

James

$223 nightly

Oct 11 - Oct 12

Total with taxes and fees

A wooden cabin with a small patio area, a table with chairs, and a bench.

12. Tiny Willow

Blandford Forum

Kenneth

$346 nightly

Oct 23 - Oct 24

Total with taxes and fees

A bathroom with a window, a sink, and two potted plants.

13. Hardy View Farm House

Dorchester

Carol S.

$242 nightly

Oct 26 - Oct 27

Total with taxes and fees

A picnic table in a grassy area with a wooden fence and trees in the background.

14. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

A stone house with a red-tiled roof, surrounded by a pond with reflections and greenery.

15. 2 bedroom accommodation in Goathill, near Sherborne

Goathill, near Sherborne

Jill Leeson

$432 nightly

Oct 31 - Nov 1

Total with taxes and fees

A stone building with a tiled roof, a wooden bench, and a sign indicating a reception area.

16. Little Norton Mill

Stoke-sub-Hamdon

Timothy Carl

$130 nightly

Nov 2 - Nov 3

Total with taxes and fees

A dining area with a round table, wicker chairs, and a view of boats at a marina.

17. Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

Poole

Lesley-Anne W.

$449 nightly

Oct 11 - Oct 12

Total with taxes and fees

A modern living room with a grey sofa, two armchairs, a coffee table, and a staircase.

18. Brand New 3 Bedroom House -Sleeps 6 - Free Parking

Poole

keith s.

$238 nightly

Oct 9 - Oct 10

Total with taxes and fees

A stone house with a tiled roof, a covered patio with a table and chairs, and a small attached structure with a window.

19. Stunning annexe near Bruton

Lamyatt

Jane

$152 nightly

Oct 12 - Oct 13

Total with taxes and fees

A modern living room with a brick wall, a dining area with a table and chairs, and a sofa.

20. Modern Apartment -Parking & WiFi

Poole Old Town

Paul

$177 nightly

Oct 11 - Oct 12

Total with taxes and fees

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Top Woolland Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

10/10 Excellent

"Had a really great stay at this hotel. The room was clean and comfortable, the staff were friendly and helpful, and the overall service was excellent. The location was also very convenient. Would definitely recommend this hotel and would happily stay here again."

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"The room was a good size, we had a family room for 5. The room was clean and tidy and good amenities in the room itself. The best aspect was the seaview which was fantastic helped by some good October weather. We didn't use the bar much as we were visiting relatives who live in Weymouth - but it looked good with plenty to do. The best thing about staying in the older hotels on the front is access to the beach/Weymouth centre, room size and view. Overall very happy with the hotel and the price. Would definitely stay again - thanks."

The Bridge House, BW Signature Collection

8/10 Good

"We stayed for 1 night at the hotel, in a lovely room at the back, overlooking the river. Everything was spotlessly clean, and the hotel is well maintained. As an electric car driver, the ability to charge the car overnight was a huge plus. Breakfast was good, fried egg, sausage, bacon etc, plus pastries and cereal available. Just two minor quibbles with the room: the air conditioning unit showed the set temperature illuminated with a very bright white light, which stopped the room from being fully dark. Luckily I had brought an eye mask. Also, the temperature of the shower was very difficult to control, the switch from the bath taps was very stiff, then it was either scalding hot or completely cold with very little room to manoeuvre between them. We managed, but a warning sign next to the taps might have been a good precaution. A very comfortable stay overall, and a very convenient location for us, we’ll be back."

Find out more about Woolland

Everything you need to know about Woolland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woolland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Woolland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woolland vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $156 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woolland rentals

At Expedia, we put the best Woolland vacation 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 Woolland 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 Woolland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woolland. 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

Can I find a vacation rental in Woolland?

Yes, we offer vacation rentals close to popular local attractions in Woolland, or you can select a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Woolland has to offer?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: This vacation home rental near Woolland comes with WiFi so you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Woolland?

Expedia has 4 vacation rentals for your stay in Woolland.

What can I see and do in Woolland?

Explore the area and family-friendly sights such as Monkey World Ape Rescue Center, or get out into nature at a spot like Dorset National Landscape. In the larger area, you’ll find Cerne Abbas Giant and Sculpture by the Lakes.

What are vacation rentals like in Woolland?

Vacation rentals are privately owned properties you can book for several days or more in Woolland. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.

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Check prices for these dates

Our top choices for Woolland vacation rentals

1. 1 bedroom accommodation in Ibberton, Blandford Forum

2. Oke Apple Cottage

3. The Orchid

4. A spacious, well equipped private annexe with garden and parking in Shaftesbury.

5. Private Luxury By The Sea

6. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

7. Beautiful NEW 3 bedroom house - garden & parking

8. Luxurious Glass House with Private Hot tub

9. Streamside Apartments

10. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

11. Brand NEW 3 bedroom house - garden & parking +wifi

12. Tiny Willow

13. Hardy View Farm House

14. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

15. 2 bedroom accommodation in Goathill, near Sherborne

16. Little Norton Mill

17. Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

18. Brand New 3 Bedroom House -Sleeps 6 - Free Parking

19. Stunning annexe near Bruton

20. Modern Apartment -Parking & WiFi

Find vacation rentals that suit your style

Top Woolland Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

The Jubilee Hotel West- with Spa Facilities

The Frampton Arms

The Bridge House, BW Signature Collection

Best Western Weymouth Hotel Rembrandt

George Albert Hotel & Spa

Crown Hotel

Holiday Inn Express Poole by IHG

Sleeping Bear Hotel Dorchester

Find out more about Woolland

Frequently asked questions

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