Osmington Vacation Rentals from $145: Search Short-Term Rentals

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Our top choices for Osmington vacation rentals

A cozy room with a stone wall, a fireplace, a sofa, and a window.

1. Norden Cottage

Weymouth

"The cottage itself is lovely, and has a lot of potential. It’s a large cottage which accomodates 5. Lighting wasn’t working in all rooms which was a nuisance and the facilities in the kitchen were dirty and not maintained well. Oven and stove worked, coffee machine filthy. Given that you would hire a cottage to do self catering, it wasn’t one of the better cottages we have stayed in. We found it a cold welcoming, no welcome note, only a small box of biscuits on entry. Cottage was really...

Hilary

$719 nightly

Nov 23 - Nov 24

Total with taxes and fees

A stone cottage with a thatched roof, a wooden deck, and a round metal table with chairs and a small table set for tea.

2. Laurel Cottage

Weymouth

$616 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a sofa, a coffee table with books, a lamp, and a view through large glass doors to an outdoor patio.

3. Woodbine Cottage

Weymouth

$823 nightly

Nov 16 - Nov 17

Total with taxes and fees

A residential property with a patio, a sliding glass door, and a brick exterior.

4. Cedar Drive

Weymouth

David

$638 nightly

Nov 19 - Nov 20

Total with taxes and fees

A cozy living room with a green sofa, a dining table set with plates and cups, and a variety of wall art.

5. Cosy Peacehaven. Free on site Parking! Pet friendly!

Weymouth Town Center

Chloe

$143 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern kitchen with a gas stove, oven, and stainless steel appliances.

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

Wool

Kristina

$335 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

7. Private Luxury By The Sea

Poole

Luke

$191 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden cabin bedroom with a bed, pillows, and a dreamcatcher on the wall.

8. Glamping Cabin - Great for Hikers - Breakfast Inc!

Swanage

Vanessa

$211 nightly

Nov 12 - Nov 13

Total with taxes and fees

A compact living space with a kitchenette, a sofa, and a large window offering a view of the outdoors.

9. Hardy View Farm House

Dorchester

Carol S.

$204 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

10. Elegant Apartment inc. Parking

Poole Old Town

Peter L.

$180 nightly

Nov 12 - Nov 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.

11. Modern Apartment -Parking & WiFi

Poole Old Town

Jo R.

$165 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

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

Poole Old Town

Richard W.

$165 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

13. Super Trendy Apartment - Free Parking & Fast WiFi

Poole Old Town

Tim H.

$165 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden table with a bottle of wine, two wine glasses, a bowl of fruit, and a brochure titled "Resort".

14. Sea Spray

Overcombe

$589 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

15. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

$184 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bed with a basket of pastries and a blanket.

16. Stylish modern retreat overlooking Poole Quay

Poole

David R.

$222 nightly

Nov 11 - Nov 12

Total with taxes and fees

A corridor with a wooden floor and a view of boats at a marina.

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

Poole

Lesley-Anne W.

$434 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

18. Beautiful Couples Retreat - FREE Parking & WiFi

Poole Old Town

Frazer

$180 nightly

Nov 15 - Nov 16

Total with taxes and fees

19. Bluebell Wood

Harman's Cross

Liam

$255 nightly

Nov 11 - Nov 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.

20. Beautiful NEW 3 bedroom house - garden & parking

Poole

Lee

$227 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Top Osmington Hotel Reviews

Fairhaven Hotel

10/10 Excellent

"We had a superior room so it was nice and big. Comfy bed and good shower. Nice decor in the room and a lovely sea view. Would be better if there was a small fridge and an iron in the room."

Holiday Inn Express Poole by IHG

10/10 Excellent

"We checked in and inputted our car registration on the desk screen. Parking is £10 per day. Staff informed us of breakfast times. Our room was very clean, lovely sheets and soft pillows. Breakfast the next morning was really good, lots of choice and very tasty. When we checked out the staff were really friendly asking if everything was okay. They couldn’t find a record of our car registration which was odd as we had entered our details! I would stay there again, was very central just a short walk into town. Good value."

The Knoll House

8/10 Good

"Overall we managed our stay within our expectations based on contact with the venue and reservations team. The hotel is in a great location just across the road from Knoll Beach and plays on its location. Food at breakfast and dinner is great and service excellent. Of particular note are Ally, Aidan, Damian and Olivia. This is a heritage hotel and tries as much as possible to balance the challenges of maintaining traditional features with the ongoing challenges of maintenance and modernisation whilst full renovation is pending. Overall, we made our stay work within our understanding of the strengths and weaknesses of the venue. A return visit would only be possible after venue changes were completed."

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."

Find out more about Osmington

Everything you need to know about Osmington 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 Osmington 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 Osmington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osmington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osmington. 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 Osmington 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 $145 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 Osmington rentals

At Expedia, we put the best Osmington 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 Osmington 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 Osmington 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 Osmington. 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 vacation rentals in Osmington?

Yes, there are vacation rentals near popular attractions in Osmington, or you can choose a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Osmington?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: You might want to consider this vacation home rental near Osmington, which 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 are there in Osmington?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Osmington stay.

What can I see and do in Osmington?

Weymouth Bay and Dorset and East Devon Coast are a couple of lovely local spots to get outside and enjoy nature. While here, Ringstead Beach and Osmington Bay Beach are other places worth a visit.

What are vacation rentals like in Osmington?

Vacation rentals are privately owned properties you can book for a couple days or more in Osmington. Vacation rentals offer extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.

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Check prices for these dates

Our top choices for Osmington vacation rentals

1. Norden Cottage

2. Laurel Cottage

3. Woodbine Cottage

4. Cedar Drive

5. Cosy Peacehaven. Free on site Parking! Pet friendly!

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

7. Private Luxury By The Sea

8. Glamping Cabin - Great for Hikers - Breakfast Inc!

9. Hardy View Farm House

10. Elegant Apartment inc. Parking

11. Modern Apartment -Parking & WiFi

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

13. Super Trendy Apartment - Free Parking & Fast WiFi

14. Sea Spray

15. 1 bedroom accommodation in Ibberton, Blandford Forum

16. Stylish modern retreat overlooking Poole Quay

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

18. Beautiful Couples Retreat - FREE Parking & WiFi

19. Bluebell Wood

20. Beautiful NEW 3 bedroom house - garden & parking

Find vacation rentals that suit your style

Top Osmington Hotel Reviews

Fairhaven Hotel

Sleeping Bear Hotel Dorchester

Holiday Inn Express Poole by IHG

The Duchess of Cornwall Inn

Crown Hotel

The Knoll House

Durdle Door Hotel

Lulworth Cove Inn

The Jubilee Hotel West- with Spa Facilities

Find out more about Osmington

Frequently asked questions

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