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Osmington Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Osmington vacation rentals

A kitchen with a microwave, a coffee maker, and a window with a view of greenery.

1. Rose Cottage

Rose Cottage
2.0 star property
Weymouth
$807 nightly
The price is $968
Sep 29 - Sep 30
Total with taxes and fees
Rose Cottage
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

Laurel Cottage
3.5 star property
Weymouth
$555 nightly
The price is $666
Oct 9 - Oct 10
Total with taxes and fees
Laurel Cottage
A bedroom with two single beds, a nightstand, a window, and a star-patterned rug.

3. Woodbine Cottage

Woodbine Cottage
2.0 star property
Weymouth
$759 nightly
The price is $911
Oct 11 - Oct 12
Total with taxes and fees
Woodbine Cottage
A cozy room with a stone wall, a fireplace, a sofa, and a window.

4. Norden Cottage

Norden Cottage
3.0 star property
Weymouth
6.0 out of 10, (1 review)
"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...
United Kingdom
Hilary
$648 nightly
The price is $778
Oct 17 - Oct 18
Total with taxes and fees
Norden Cottage
A room with large windows offering a view of a coastal landscape.

5. Waterson

Waterson
3.0 star property
Weymouth
8.0 out of 10, Very good, (1 review)
"lovely location , inside house a little tired "
United Kingdom
Nigel
$1,018 nightly
The price is $1,221
Oct 11 - Oct 12
Total with taxes and fees
Waterson
A beach with people, a large striped tower, and buildings in the background.

6. The Sailors Studio|Sleeps2|Weymouth Beach|

The Sailors Studio|Sleeps2|Weymouth Beach|
Weymouth Town Center
$172 nightly
The price is $172
Sep 28 - Sep 29
Total with taxes and fees
The Sailors Studio|Sleeps2|Weymouth Beach|
A beach with a natural rock arch formation.

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

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Wool
10.0 out of 10, Exceptional, (5 reviews)
"The house was outstanding, probably the best we’ve ever experienced. It is exceptionally clean, comfortable for our family of 5, and convenient to the sites in the area. We would stay there again if we return."
United States
Kristina
$362 nightly
The price is $362
Sep 27 - Sep 28
Total with taxes and fees
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
A cozy living room with a green sofa, a dining table set with plates and cups, and a variety of wall art.

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

Cosy Peacehaven. Free on site Parking! Pet friendly!
Weymouth Town Center
9.4 out of 10, Exceptional, (3 reviews)
"Perfect flat which contained everything we needed for a great stay. It is in an excellent location and parking was a great bonus to us. Communication was great with clear instructions and thoughtful little extras."
United Kingdom
Chloe
$168 nightly
The price is $168
Oct 6 - Oct 7
Total with taxes and fees
Cosy Peacehaven. Free on site Parking! Pet friendly!
A bedroom with a bed, pillows, a red blanket, and a window with plants.

9. Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!
Weymouth Town Center
8.4 out of 10, Very good, (5 reviews)
"Lovely property, well equipped and comfy beds"
United Kingdom
Kim E.
$185 nightly
The price is $185
Oct 6 - Oct 7
Total with taxes and fees
Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!
A bedroom with a bed, a wooden chair, a desk with a mirror, and a window with curtains.

10. Sea Spray

Sea Spray
3.0 star property
Overcombe
$531 nightly
The price is $638
Oct 2 - Oct 3
Total with taxes and fees
Sea Spray
A neatly made bed with two towels folded into robes, a pillow, and a small card on the bed.

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

Glamping Cabin - Great for Hikers - Breakfast Inc!
3.0 star property
Swanage
10.0 out of 10, Exceptional, (1 review)
"Very welcoming and ideal for travellers with pets . Great location , walking distance to the coastal path and very close drives to National Trust areas such as Corfe Castle and Studland beaches"
United Kingdom
Vanessa
$191 nightly
The price is $191
Oct 6 - Oct 7
Total with taxes and fees
Glamping Cabin - Great for Hikers - Breakfast Inc!
A modern outdoor patio with wicker furniture and a glass door leading to a covered area.

12. Private Luxury By The Sea

Private Luxury By The Sea
Poole
9.6 out of 10, Exceptional, (8 reviews)
"Perfect place and very quite lovely and cosy. Thanks Richard👍👍"
United Kingdom
Richard
$202 nightly
The price is $202
Sep 27 - Sep 28
Total with taxes and fees
Private Luxury By The Sea
A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

13. 1 bedroom accommodation in Ibberton, Blandford Forum

1 bedroom accommodation in Ibberton, Blandford Forum
Ibberton, Blandford Forum
10.0 out of 10, Exceptional, (11 reviews)
"Lovely place, lovely countryside."
United States
Paul Mitchell
$216 nightly
The price is $216
Oct 2 - Oct 3
Total with taxes and fees
1 bedroom accommodation in Ibberton, Blandford Forum
A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

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

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Winterborne Whitechurch
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Stacia B.
$469 nightly
The price is $469
Oct 26 - Oct 27
Total with taxes and fees
The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
A dining area with a round table, wicker chairs, and a view of boats at a marina.

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

Classic Yacht Nadine with Hot Tub, Poole Harbour Bay
Poole
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely amazing stay! Wish it was for longer! The boat could have had some extra TLC but otherwise we will definitely return!"
United States
Lesley-Anne W.
$420 nightly
The price is $420
Sep 28 - Sep 29
Total with taxes and fees
Classic Yacht Nadine with Hot Tub, Poole Harbour Bay
A modern living room with a brick wall, a dining area with a table and chairs, and a sofa.

16. Modern Apartment -Parking & WiFi

Modern Apartment -Parking & WiFi
Poole Old Town
9.0 out of 10, Wonderful, (8 reviews)
"Apartment was very clean and well equipped, with parking behind the building and very close to pubs, cafe and restaurant along the waterfront. "
United Kingdom
Paul
$177 nightly
The price is $177
Sep 27 - Sep 28
Total with taxes and fees
Modern Apartment -Parking & WiFi
A modern interior with a glass partition, a carpeted floor, and a visible kitchen area in the background.

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

Luxury ⭐⭐⭐⭐⭐- Near Sandbanks BEACH! Netflix & WiFi
Poole
9.4 out of 10, Exceptional, (25 reviews)
"The property was clean and inviting. Perfect for our family. We really enjoyed our stay!!! "
United Kingdom
malka l.
$242 nightly
The price is $242
Sep 27 - Sep 28
Total with taxes and fees
Luxury ⭐⭐⭐⭐⭐- Near Sandbanks BEACH! Netflix & WiFi
A bedroom with a large mirror, a bed, a chair, and a window with curtains.

18. Beautiful Couples Retreat - FREE Parking & WiFi

Beautiful Couples Retreat - FREE Parking & WiFi
Poole Old Town
10.0 out of 10, Exceptional, (5 reviews)
"Lovely clean flat in the PERFECT location in Poole, very easily accessible and great communication with host throughout. Would recommend - 5* "
United Kingdom
Frazer
$208 nightly
The price is $208
Oct 1 - Oct 2
Total with taxes and fees
Beautiful Couples Retreat - FREE Parking & WiFi
A hotel room with a bed, green sofa, and a glass coffee table with a vase of flowers.

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

Chic Modern Apartment Suite - Free Parking & WiFi!
Poole Old Town
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was very clean and comfortable. It is stylishly furnished and extremely centrally located. The secure parking, in such a central location as a real plus. It is literally moments on foot from the quay. We would not hesitate to stay here again."
United States
Richard W.
$193 nightly
The price is $193
Sep 27 - Sep 28
Total with taxes and fees
Chic Modern Apartment Suite - Free Parking & WiFi!
A living room with a television, dark-colored furniture, a white door, and a window with blinds.

20. Chandlers Nook

Chandlers Nook
2.0 star property
Portland
$429 nightly
The price is $515
Oct 5 - Oct 6
Total with taxes and fees
Chandlers Nook
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 Osmington Hotel Reviews

Sandbanks Hotel

Sandbanks Hotel

10/10 Excellent
"Fabulous stay The upgrade was Huge!! All Staff are so friendly and very nice..breakfast was delicious and a good variety I could literally touch the sand from my deck..so beautiful and amazing stay Next time all I want more is a small fridge and safe box the view was fantastic watch the tide and walk on the powder soft sand"
RITA 6-night trip
Posted 4 hours ago
Sandbanks Hotel

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 $202 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: Visitors like this Osmington vacation home rental. It 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.