Osmington

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Entertainment

Bathtub

Bathroom

Cooking Essentials

Freezer

Fridge

High Chair

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Kitchen & Dining

Cot / Crib

Washing Machine

Bedroom & Laundry

Wi-fi

Internet & Office

Fireplace

Heating & Cooling

Parking Available

Private Entrance

Parking & Access

Garden

Outdoor Seating

Patio / Terrace

Outdoor

Pets Allowed

Pets

Child Friendly

Other

You’ll find this characterful cottage in Osmington village on the Jurassic Coast. Perfect for a family or group of friends, with a wood-burning stove and roll-top bath, this home invites relaxation – just be careful with your head and those sloping ceilings. But it’s not all about cosying up in winter here, as the garden offers the ideal spot for alfresco dinners or evening aperitifs. Locally, you’ll find the South West Coastal Path on your doorstep, or drive to vibrant Weymouth for shops, eateries and, of course, the iconic beach. 

Jurassic Coast Hideaway

Library of Books

Hair Dryer

Kettle

Toaster

Private Washing Machine

Laptop Friendly Workspace

Central Heating

Free Parking On Premises

Balcony

Fenced Garden

Fire Extinguisher

Smoke Detector

For those who have been dreaming of a chocolate-box cottage break, we may have just the ticket. This charming little abode blends old-world charm with modern convenience along Dorset's Jurassic Coast. Rich in dramatic scenery, white-sand beaches, and picturesque fishing villages, this is the perfect destination for those with a car and a love of adventure. Or, if you're keen to get out on foot, you'll find Osmington Mills complete with a local pub and tea room just a short walk away. All that being said, when staying in such a pretty thatched cottage, you may end up simply spending your time cosied up with a good book or stargazing from the private terrace. 

Thatched Hideaway

Nintendo Wii

Board Games

DVD Library

DVD Player

Games Console

Sound System

Heated Towel Rail

Dishwasher

Private Dryer

Dryer

Free Parking On Street

Fenced Property

Carbon Monoxide Detector

If you've been dreaming of a chocolate box cottage for your next coastal escape, this thatched roof abode may do the trick. Surrounded by manicured lawns that are perfect for a picnic or your four-legged friends to roam free, you can spend the warmer days dining alfresco or splashing around at the beach. At night, cosy up by the fire with a good book, or walk across the field for a pint in the local pub. With the Jurassic Coast's top sights only a short drive away, and lots of local amenities within walking distance, you truly have the best of both worlds at this charming little cottage along England's south coast.

Ocean View Inn

Amazon Prime

Netflix

Streaming Services

Luxury Toiletries

Toiletries

Blender

Cafetiere

Coffee Maker

Espresso Machine

Trash Compactor

Wine Cooler

Black-Out Blinds

Cleaning Products

Drying Rack

Hangers

Iron

Ironing Board

Luxury Bedding

Heated Pool

Indoor Pool

Private Pool

Exercise Equipment

Hot Tub

Jacuzzi

Sauna

Sauna / Steam Room

Steam Room

Swimming Pool

Wellness & Fitness

Desk / Workplace

Temperature Control

Private Parking

Early / Late Check-Out Available

Self Check-in / Check-out

Barbeque

Pool House

Sun Loungers / Beach Chairs

Sun Umbrellas

Throws

Umbrellas

Welcome Hamper

Nice to haves

First Aid Kit

Stair Gates

Live a life of luxury on the Dorset coast in this prestigious home. Not only is the main house spacious and impeccably decorated, but there's also a separate building at the foot of the garden that houses a swimming pool, sauna and hot tub. Sounds like the kind of place that's difficult to leave.

We love the slick style aesthetic that's adopted throughout the home, from the plush Chesterfield sofas to the mirrored furniture in the double suites. Opting for a palette of charcoal grey with brick and marble accents, your hosts have made a strong case for monochrome interiors. When you're not lounging in the open-plan living area, glide across the manicured lawn and have a leisurely dip in your private pool. Come evening, the wood-burning stove creates a cosy and relaxing atmosphere.

If you can pull yourself away, wander down to Weymouth harbour and watch the fishing boats come and go. Past picturesque streets lined with quirky cafés, you'll reach a stretch of white-sand beach. On bright days, this idyllic expanse feels like it could be anywhere in the world.

Marble & Charcoal

Free Parking

With three pubs just moments away, as well as convenience stores, you'll have everything you need for a comfortable stay. This home is also just a stroll from Bowleaze Cove and a short drive from Weymouth with its bustling harbour and sandy beaches. After all that exploring you’ll need a comfy home to return to and this place fits the bill. We love the log burner in the living room and the garden is perfect for family and friends to relax in.

Bowleaze Breeze

This little hideaway is nestled in the residential area of Bowleaze Coveway – just a mile from the heart of Weymouth. You can stroll towards the seafront or adventure further afield to West Bay and the Jurassic Coast. It’s worth noting you may hear some street noise during your stay, but you will have private parking as well as access to a garden. Inside, the rooms are simple, cosy and well suited to couples and solo travellers in search of an easygoing coastal getaway. 


Breezy Cottage

Record Player

Rain Shower

Pod Coffee Machine

Vacuum Cleaner

Safe

Step through this cottage's pink front door and you'll find breezy living spaces bathed in light and more than enough room for the whole family to spread out. The pared-back design has some subtle coastal influence – no surprise, given the proximity to Weymouth Harbour – and features like traditional ornamental fireplaces and vintage furniture add just a touch of character.

Days at this beachy retreat begin and end in the lovely garden – start the morning off with a cup of coffee in the early sunlight, then finish the night with a barbecue and a couple of glasses of wine on the cosy outdoor sofa. Not much of a grillmaster? The chic kitchen has everything you'll need to rustle up Sunday roasts and tasty baked goods. During chillier weather, throw a log on the wood-burner and hole up in the lounge with a good book, play a board game around the table or settle down for a Netflix movie night. There's also a record player to set the mood.

Location-wise, you're just a six-minute stroll from Weymouth Harbour and fourteen from Weymouth's award-winning beach. When you're not enjoying fish and chips by the water or lounging in the sand, spend your afternoons discovering the town's trendy art galleries, boutique shops and array of pubs and eateries. Walks along the Jurassic Coast are easily reached by car, but with so much on your doorstep, who'd want to leave?

Sweet Like Taffy

Satellite / Cable TV

Playground

Outdoor Pool

Shared Pool

Access to Gym / Spa

Tennis Court

Access to Beach

Set within a holiday park surrounded by West Dorset’s beautiful countryside, this home offers a retreat that can be as active or as relaxed as you wish it. The park’s shared amenities include a communal heated pool and spa access for when you want to tap into easy holiday living, while the tennis courts, watersports opportunities and gym help you dial up the energy whenever you need. The holiday complex also has a beach for ample sun-soaking, while the two-storey home’s private water-facing deck is ideal for alfresco meals and sundowners. End the night with a glass of wine by the living room’s fire, and you’ll be in holiday mode in no time. 


Sails in the Summertime

EV Charger

This charming barn is a hidden gem nestled in West Dorset. An ideal spot for adventure-seekers with an array of activities on offer, including a heated infinity pool, private spa, water sports, tennis and forest playgrounds (to name just a few), you’ll never be short of things to see and do. The home itself is set over three levels, offering plenty of space for up to eleven guests to spread out in complete comfort. And the cherry on this particular cake is definitely the outdoor space, with decking and a balcony overlooking the lake, and even a private jetty for those keen to get straight out onto the water. 


A Perfect Match

Situated on a holiday park in West Dorset, this family-friendly home overlooks the lake and provides comfortable spaces for the whole group to kick back and relax. Outside, there’s a large deck with lounge seating and although there isn’t an alfresco dining table, the kitchen diner’s sliding doors open wide for an indoor-outdoor living experience. Guests staying here have access to a range of communal amenities, from forest playgrounds to a spa. And if you’d like to explore a little, rent bicycles for a ride around the surrounding area or jump in the car and take the twelve-minute drive to Eweleaze Beach.

Ivy & Sage

Smart TV

This apartment in the heart of Weymouth is a wonderful option for families. The bright living area makes relaxing together easy – there's a comfortable sofa, a well-appointed kitchen, and a table where you can tuck into delicious dinners. Need a little time to yourself? The main bedroom has its own snug, perfect for morning coffees. There isn't any outdoor space here, but the beach is just a short walk away. Weymouth Harbour is also nearby, while Dorchester is within easy driving distance if you fancy a change of scenery.

Happy Cove

Take in the views over the sea from this apartment’s living room – the vistas through the large Georgian windows are stunning. Okay, the kitchen is compact, but it has everything you need to create some home-cooked food. Or if you prefer to eat out, there are plenty of eateries on your doorstep. This apartment is on the esplanade, just steps away from Weymouth Beach so the location couldn’t be better. Other places of interest nearby include Portland Castle, Chesil Beach and Abbotsbury Subtropical Gardens.

Esplanade Retreat

Parking On Street

This cottage is in the heart of Weymouth, just steps from the harbour and a short walk from the beach. As far as locations go, you can't fault it – families and friends will have all they need on their doorstep. An eclectic medley of vintage pieces and contemporary design, every room back home is the definition of warm and welcoming. Upstairs, the main bedroom boasts beautiful sea views that make waking up a dream. There's also a patio outside for relaxing on warm afternoons – no wonder it ticks all our boxes.

Brine & Brew

Desk

Courtyard

Welcome to this former fisherman's cottage, which has been beautifully restored. The living space is a great place to relax, and the kitchen is well-appointed. Set over three floors, the stairs are quite steep, but the rewards are comfy bedrooms. Outside, there’s a small courtyard – perfect for breakfast or evening drinks. When you want to explore Weymouth, you can start by checking out the Tudor House opposite, one of a few remaining in the town. Just a minute away is Hope Square, with its restaurants and friendly pub. You’re also only moments from the old harbour with its yachts and fishing boats. Or if you want a day at the beach, Weymouth’s main beach is just a five-minute walk away. 

Harbourside Anchor

There’s adventure in abundance at this home within a lakeside holiday park. You can launch kayaks and paddle boards from the lakeside beach, spend days playing tennis or swimming in the shared pool, or indulge in a spa session. With forest playgrounds, biking trails and a rooftop bar all onsite, it’s a great spot for families. A state-of-the-art kitchen has everything you need for self-catering and dinner can be served al fresco, on the private terrace. A wood-burner in the open living area keeps things cosy.  

The Arty Cottage

With stunning views of the beach and sea, this apartment is the perfect seaside getaway. You can enjoy the vistas from the sun loungers on the private terrace and from inside with its character features. And, while the kitchen is compact, it has everything you probably need for making some home-cooked meals. Just moments from the shore, the location is perfect for strolls. Or have a short walk into Weymouth town centre, where you’ll find plenty of shops, restaurants, and cafes, as well as the harbour. 

Ocean & Beach Views

In the heart of Weymouth, steps away from the charming harbour, this home is in an enviable location. You can get a glimpse of the harbour from the main bedroom. We love that you can drop your bags and head straight for the waterfront for a pint, take the dog on a walk along the beach (just 0.2 miles away), or savour the seaside sunshine from your courtyard. Some of the furniture is a little tired and the living area isn’t the best for cosy film nights, but the natural light beaming through the windows brightens every corner of the home for cheerful breakfasts around the rustic dining table. 

Sun at Daybreak

Sitting confidently on the edge of Beaumont Lake, It’s not hard to see why this home caught our eye. Designed to bring ease and comfort to family living, you’ll be welcomed by sweeping views and plenty of space to sit back and soak it all in. There’s also direct access to the lake for swimming or canoeing. You will have access to a wide range of estate amenities – including a spa, an outdoor heated swimming pool and tennis courts. 

The Dorset Dancer

Paid Parking

You couldn’t ask for a better address really with this home. It overlooks the English Channel and Weymouth Beach. There’s plenty of natural light from the floor-to-ceiling windows in this split-level apartment and we love the open-plan living space. Okay, more about its fantastic location. As well as the beach being just steps away, you’ll be able to explore all of the award-winning cafes and restaurants on your doorstep. Other attractions worth visiting include the historic ruins of Sandsfoot Castle, Nothe Fort and Sandworld Weymouth.

Golden Sand

Right on Weymouth's beachfront, this home blends old-school British seaside charm with contemporary comfort. Spread across three floors, there's plenty of space to gather and unwind, with uninterrupted views over the sea. No need to worry about the car — the historic harbour’s just a stroll away, brimming with seafood spots, cosy pubs, and quirky shops. But if you’re feeling adventurous, the jaw-dropping Jurassic Coast is right on your doorstep, with iconic spots like Durdle Door and Lulworth Cove just a short drive away.

British Beachside Bliss

Right on Weymouth's lively seafront, this studio apartment is a great fit for couples. You won't have to travel far to visit the beach or harbour – both are practically on your doorstep. Pubs, bars, and restaurants (including one downstairs) are also nearby – it can get a tad noisy, but that's the charm of being so central. Besides, the coastline views from the Georgian windows are something special. Wake up to the waves crashing on the pebbled beach, then finish the day with a glass of wine as the sun goes down on the horizon. That's bliss.

Coastal Wonder

Resort Access

Nestled on the water’s edge, this home has relaxation at its core. Inside is comfortable and homely, while the outdoor space boasts decking and opportunities for alfresco dining – all while enjoying the lake views, naturally. With an abundance of on-site activities, you don’t need to head further afield if you don’t want to, as there’s more than enough to occupy you here. Water sports, nature trails, cycling, yoga, swimming in the communal pool or simply indulging in dinner from the on-site pizza shack – the opportunities are endless. 

Little Butterflies

Only a stone's throw from Weymouth Beach, this home is a romantic getaway on the Dorset coast. A variety of shops, eateries, and pubs are nearby, and it's only a twenty-minute walk to the picturesque harbour. You won't find any outdoor space here, but the living room has a Juliet balcony where you can enjoy fresh air. There's also plenty of space across the three floors. With its soaker bath, en-suite shower room, and bed tucked under the eaves, the main suite is the definition of cosy. The ground-level storage room is cherry on top, perfect for bikes and beach gear.

Coastal Romantic

Seconds from the bay and its sandy sheltered beach, this slick two-storey apartment is great for couples or solo travellers keen to explore Weymouth and the south coast. Through the ground floor entrance you'll find an attractive open plan living area, featuring a kitchen and dining table for home cooked meals or enjoying bites from local businesses. Upstairs is a bright and comfortable bedroom, a bathroom, and doors leading out to a charming patio terrace, where you can enjoy a drink and a paperback in the English sun. The location is also excellent – Weymouth's many independent shops and restaurants are right on your doorstep, while parks, lakes, seafronts, and other quaint towns can all be reached easily by car.

Seaside Love

If you’re looking to experience the magic of the English countryside, this 17th-century thatched cottage delivers the perfect solution. Nestled in the little town of Winfrith, it’s just a five-minute drive to the Jurassic Coast and some of the most beautiful spots in Dorset. There’s also a village shop and a pub within walking distance and you’ll find private parking alongside the cottage. Inside, the rooms are cosy, classic and full of charm. There’s a fireplace in the living room along with board games for relaxing evenings at home. You’ll also have access to a little garden with a barbecue for warm weather days. 

Rose of the Heart

Originally built as a bunker for the RAF in 1941 and decommissioned in 1956, this truly remarkable home has been thoughtfully redesigned with its Grade II listing in mind. Retaining its original concrete walls as well as a range of other elements, this is a home you won’t soon forget – offering three bedrooms, two bathrooms and surrounded by the picturesque Dorset countryside, it’s simultaneously idyllic, modern and historic. A private garden awaits outside, and beyond, a quaint woodland teems with quiet natural beauty. When you’re ready to explore further afield, the gorgeous Dorset coast is just a five-minute drive away. Get ready to be wowed.

The Bunker

Just a short stroll from Weymouth’s award-winning beach, this contemporary home is an ideal base for friends or family on a seaside stay. The cosy courtyard is a perfect spot for your morning coffee, while the sleek kitchen will have you rusting up family favourites in no time. With Weymouth beach within easy reach, adrenaline-seekers can get their kicks paddle boarding or kayaking, or you can simply relax – there’s something for everyone here. Slightly further afield, a trip to Portland and the iconic Portland Bill lighthouse is a must, as is a visit to Chesil beach. 

Coastal Charms

Sitting on a fantastic complex on the beautiful Beaumont Lake in Dorset, this home is ideally placed for exploring the Dorset AONB, which includes some great seaside spots such as Durdle Door. The home itself is simple and stylish, but what will make your stay special is enjoying access to the site's marvellous facilities, including a communal heated pool, shared gym and spa, plus the lake for water sports, equipment for which you can hire at the on-site activity centre.

The Piazza

Set within a lakeside holiday estate in West Dorset, this two-level home is all about taking advantage of the great outdoors on its doorstep. Communal access to the on-site heated swimming pool, spa and restaurant ensure plenty of relaxing downtime, while the gym, tennis courts, children’s playground and array of watersports on offer are on hand for when you wish to ramp up the activity level. The holiday site also boasts access to a beach where you can while away sunny hours on the sands. And after a fun-filled day, there’s no better way to end the evening than with an alfresco meal on the private patio, followed by a glass of wine by the living room’s fire. 


The Dorset Rose

Moments from Weymouth Harbour and less than a mile from the beach, this home puts the Dorset coast on your doorstep. You couldn't ask for a better location. Shops, restaurants, and, most importantly, the sea are all a short walk away. Back home, there's a breezy living area, a well-appointed kitchen, and a deck for alfresco aperitifs. With four comfortable bedrooms, it's ideal for families and groups. Just note that one bedroom is a little tight, and the fourth has three single beds, ideal for little ones.

Weymouth Wonder

Extra Pillows and Blankets

Connected to the mainland by a tombolo, the isle of Portland is a pretty spot off the Dorset Coast. This chic house is in the village of Fortuneswell in the north of the island, and it makes the perfect place to begin your adventures. 

The home effortlessly blends contemporary chic with traditional charm, creating a welcoming atmosphere that isn't short on style. Take in the stunning sea views from the top floor master bedroom – binoculars provided, or get cosy around the fireplace in the living room with a glass of wine and a good book; you can take your pick from the squashy sofa and the retro hanging egg chair. There's also a fantastic dining space, complete with an exposed stone wall where you can share a delicious home-cooked feast with your guests. 

This home might not have its own outdoor space, but it is only an three-minute walk away from the eighteen-mile long pebbly Chesil Beach. Paddle in the water, then enjoy a long coastal walk as you breathe in the fresh air. And, if you take a ten-minute drive to the south of the island, you can visit the historic Portland Bill Lighthouse and admire the curious Pulpit Rock too. 

Island Tides

Perfect for family holidays in the country that aren't too far from the city, this bright modern home has much to admire. Its sleek open plan interiors are elevated by thoughtful touches, including a log burning fire, a welcome pack, and two passes for the on-site spa. Upstairs you'll have a choice of three bedrooms (though little ones may bag the bunk bed), while outdoors you'll find your own private hot tub. Though some neighbouring homes are still under construction, the holiday village this home is part of has some premier facilities, including a shared pool and tennis court. You'll also be less than half an hour from the south coast, in reach of Weymouth and other charming harbour towns.

The Country View

Set amid acres of woodland home to native wildlife, this family-friendly cottage sits on a private estate, boasting a heated pool, spa treatments, watersport activities on the freshwater lakes, and much more. The log burner is a cosy touch, and curious kids will find a telescope for stargazing before bedtime – practical baby cots and highchairs are also available to rent. Hiring a car comes recommended, as Dorchester is a lovely drive away, and the Dorset coast offers striking scenery and excellent seafood.

The River to the House

Air Conditioning

This lakeside sanctuary sits peacefully on the edge of a private Dorset estate. Perfect for families seeking fun and relaxation, you’ll find plenty to keep everyone entertained. From the hot tub and garden to the private jetty, this is the ideal base from which to begin your lakeside adventures. There’s also a range of estate facilities, including a spa, swimming pool, tennis courts and a forest playground. And while you will have neighbours close by, the private terrace offers a wonderful sense of seclusion. 

Dorset Calm

Offering a tranquil escape on the Jurassic Coast, this charming cottage is perfect for a family. It’s less than a five-minute walk from the sandy beach at Castle Cove and the Rodwell Trail. You can walk to Weymouth Harbour and the Blue Flag beach in around twenty minutes, too. The house itself has a comfortable living space and a fully equipped kitchen. Best of all, you’ll have plenty of outside space to enjoy – sip coffee on the breakfast terrace while little ones play on the swing under the apple tree. 


Cottage Greens

Underfloor Heating

If you love history, this former transmitter bunker serving RAF Ringstead during the Second World War will really appeal. Now a Grade-II listed home, it has stunning views over the sea from both the south-facing terrace and the living space. With its original concrete walls, there’s a modern loft vibe here and there are creature comforts such as underfloor heating and a log burner. Located on the owner's dairy farm in the Dorset Area of Outstanding Natural Beauty in Ringstead Bay, you’ll be just two fields away from the sea.

A Cottage by the Sea

This family-friendly home in West Dorset is a true gem for adventure-seekers, with plenty of communal amenities, including a heated infinity pool, a spa, tennis courts and water sports. Plus, at the property, you’ll find a private jetty and an EV charging point. Views of the lake and Wakeling Island are to be enjoyed from the abode’s enclosed decking area and first-floor balcony, or if the weather’s not on your side, the living area is a comfortable place to relax, thanks to the log-burning stove. 

Dorset Daze

Laundry Supplies

Right in the heart of  Martinstown village, itself a part of Dorset’s Area of Outstanding Natural Beauty, this converted barn is the perfect getaway for couples wanting a quiet retreat. Blending modern decor with many of its original Elizabethan features, this home is a celebration of comfort and style. The thick stone and flint wall running the length of this home lets you see the age of the building, alongside a timber-gabled ceiling and flagstone floor. It’s in the style of a super spacious studio, with sliding barn doors separating the bedroom from the living area. Keeping the whole space open means you can enjoy the warmth of the wood-burner in the bedroom on chilly evenings too. If it’s sunny, there’s a private patio with a barbecue to make the most of the evening light. Plenty of bridleways, cycle routes, and public footpaths are all on the home’s doorstep and the Jurassic coastline is just five miles further south. A traditional pub and a village shop are both within walking distance. And, being only a twenty-minute drive from Weymouth's iconic harbour and beach, you’re never too far from an excellent restaurant or coastal walk. 


The Cowshed

Book a stay in one of the best homes in Osmington

We selected the 838 homes worth renting in this location

Who's coming along?

Home spotlights in Osmington

We selected the top 3% holiday homes in Osmington

Most popular homes in Osmington

Check upcoming rates & availability for Osmington

Frequently asked questions