Woolland Vacation Rentals from CA $265: Short-Term Rentals for 2026

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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

CA $334 total

includes taxes & fees

Oct 2 - Oct 3

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

2. Oke Apple Cottage

Blandford Forum

Nazir

CA $882 total

includes taxes & fees

Sep 17 - Sep 18

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

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

Shaftesbury Dorset

Martin K.

CA $220 total

includes taxes & fees

Sep 14 - Sep 15

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

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

Winterborne Whitechurch

Cord

CA $685 total

includes taxes & fees

Sep 16 - Sep 17

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

5. Streamside Apartments

Yeovil

Anonymous traveller

CA $206 total

includes taxes & fees

Oct 1 - Oct 2

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

6. Hardy View Farm House

Dorchester

Carol S.

CA $285 total

includes taxes & fees

Sep 6 - Sep 7

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

7. 2 bedroom accommodation in Goathill, near Sherborne

Goathill, near Sherborne

Jill Leeson

CA $574 total

includes taxes & fees

Sep 19 - Sep 20

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

8. Private Luxury By The Sea

Poole

Luke

CA $265 total

includes taxes & fees

Oct 4 - Oct 5

A beach with a natural rock arch formation.

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

Wool

Kristina

CA $629 total

includes taxes & fees

Oct 1 - Oct 2

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

10. Stunning annexe near Bruton

Lamyatt

Jane

CA $215 total

includes taxes & fees

Sep 9 - Sep 10

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

CA $340 total

includes taxes & fees

Sep 9 - Sep 10

A coastal landscape with a curved bay, cliffs, and a beach.

12. The Old Stables

Blandford Forum

CA $868 total

includes taxes & fees

Sep 16 - Sep 17

A modern living room with a sofa, a round table, and a television mounted on the wall.

13. Elegant Apartment inc. Parking

Poole Old Town

Peter L.

CA $294 total

includes taxes & fees

Sep 6 - Sep 7

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

14. Modern Apartment -Parking & WiFi

Poole Old Town

Paul

CA $294 total

includes taxes & fees

Sep 6 - Sep 7

A hotel room with a bed, green sofa, and a glass coffee table with a vase of flowers.

15. Chic Modern Apartment Suite - Free Parking & WiFi!

Poole Old Town

Richard W.

CA $316 total

includes taxes & fees

Sep 6 - Sep 7

A modern interior with a glass partition, a carpeted floor, and a visible kitchen area in the background.

16. Luxury ⭐⭐⭐⭐⭐- Near Sandbanks BEACH! Netflix & WiFi

Poole

malka l.

CA $338 total

includes taxes & fees

Sep 10 - Sep 11

A living room with a sofa, a coffee table, a bookshelf, and a mounted TV.

17. Super Trendy Apartment - Free Parking & Fast WiFi

Poole Old Town

Tim H.

CA $316 total

includes taxes & fees

Sep 9 - Sep 10

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

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

Poole

Lesley-Anne W.

CA $623 total

includes taxes & fees

Oct 5 - Oct 6

A bedroom with a large mirror, a bed, a chair, and a window with curtains.

19. Beautiful Couples Retreat - FREE Parking & WiFi

Poole Old Town

Frazer

CA $337 total

includes taxes & fees

Sep 7 - Sep 8

A marina with boats docked, a statue in the foreground, and buildings in the background.

20. The Lighthouse Suite|Sleeps4|Weymouth Beach|

Weymouth Town Center

"Property very difficult to find as out of date pictures & false impression of outside. Property inside was fairly clean. But access stairs & Outlook really let it down as not clean. Apartmentment was well equipped & comfortable. Sadly shower was not working nor was the fan in the bathroom. It is however in a very noisy area late at night & early in the morning, so personally would not stay here with children. However it is very close to all amenities."

Lynn

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Top Woolland Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

8/10 Good

"Only spent 1 night there in a small single room in the East wing, exactly as advertised though, small but comfortable bed, good value for money in my opinion. Paid for the buffet breakfast on the day, good value for money though even at the higher rate. Evening in the bar waa quite lively considering the time of year. Would recommend."

Best Western Weymouth Hotel Rembrandt

10/10 Excellent

"We were welcomed by friendly staff, Clare at reception was great. The Hotel was exceptionally clean. The room was well furnished, beds comfortable. Facilities were perfect. Bar and restaurant very comfortable. We had evening meal and breakfast both well cooked and a great variety at breakfast. Bar staff worked hard and remembered our drink choices . We saw a cleaner working in the lobby she was very attentive, the hotel was spotless . The Spa was relaxing. We saw locals comingni to use the pool which says alot for the hotel facilities . Its a flat 5 minute walk to the beachfront. Plenty of parking spaces. Will definitely return."

The Frampton Arms

8/10 Good

"On arrival, mid afternoon on a Saturday, bar tables were not cleared or wiped plus the floor could of done with a good sweep, on booking in we found the room to be of a good standard, we had dinner in the restaurant and the food was excellent, but again on getting refill drinks we had to ask for the used glasses to be removed. Coming down to breakfast Sunday morning, everything was great, the young man on duty making sure tables was cleared and wiped, breakfast items replenished and fresh coffee maintained, Well done him, Sundays roast was good but Monday morning things could of been a lot better, I asked if there was any tea spoons, and one was produced from behind the bar, sadly breakfast items were not replenished , and the area was not kept clean or tidy!!! Well done to the guy who did breakfast Sunday morning, 30/8"

The Manor Hotel by Greene King Inns

10/10 Excellent

"The single room was fine and reasonable value (the doors do shut loudly). The staff were all very friendly, helpful and impressive (excepting one rather sour lady behind the bar!). They were very polite and kind, it makes a big difference to how you feel about a hotel. The food was really good and not expensive, excellent value. The drinks selection was extensive. There's plenty of outside seating. All in all, I definitely recommend the hotel and would happily stay there again."

Find out more about Woolland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woolland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Sherborne Castle.

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

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

5. Streamside Apartments

6. Hardy View Farm House

7. 2 bedroom accommodation in Goathill, near Sherborne

8. Private Luxury By The Sea

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

10. Stunning annexe near Bruton

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

12. The Old Stables

13. Elegant Apartment inc. Parking

14. Modern Apartment -Parking & WiFi

15. Chic Modern Apartment Suite - Free Parking & WiFi!

16. Luxury ⭐⭐⭐⭐⭐- Near Sandbanks BEACH! Netflix & WiFi

17. Super Trendy Apartment - Free Parking & Fast WiFi

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

19. Beautiful Couples Retreat - FREE Parking & WiFi

20. The Lighthouse Suite|Sleeps4|Weymouth Beach|

Find vacation rentals that suit your style

Top Woolland Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

Fairhaven Hotel

Best Western Weymouth Hotel Rembrandt

The Bridge House, BW Signature Collection

The Frampton Arms

Sleeping Bear Hotel Dorchester

TheHillbrookSherborne

Lulworth Cove Inn

The Manor Hotel by Greene King Inns

Find out more about Woolland

Frequently asked questions

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