Isle of Portland

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Netflix

Amazon Prime

Board Games

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Dishwasher

Microwave

Cafetiere

Freezer

Kitchen

Oven

Stove

Kitchen Utensils

Toaster

Fridge

High Chair

Coffee Maker

Cooking Essentials

Kettle

Kitchen & Dining

Black-Out Blinds

Iron

Washing Machine

Dryer

Cleaning Products

Drying Rack

Extra Pillows and Blankets

Bedroom & Laundry

Wi-fi

Internet & Office

Fireplace

Central Heating

Heating & Cooling

Free Parking On Street

Private Entrance

Self Check-in / Check-out

Parking & Access

Access to Beach

Outdoor

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Smoke Detector

Other

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

Underfloor Heating

Parking On Premises

Parking Available

Garden

Outdoor Seating

Patio / Terrace

Pets Allowed

Pets

A stone's throw from Chesil Beach, this pet-friendly townhome couldn't be better placed for a seaside getaway. The Isle of Portland is home to many coastal walks and panoramic lookouts – they're all within easy reach, while Weymouth is just a short drive away. Back home, you can rest weary feet in the bright living room, whip up dinner in the large kitchen, or enjoy sundowners on the private patio. The bedrooms are a little snug, especially those on the top floor, but the home has everything you need for a laid-back stay.

Mariner's Song

Child Friendly

Escape to the stunning Jurassic Coast and stay at this coastal retreat. It’s just along the shore in Castletown on the Portland peninsula, making this an excellent choice for a seaside getaway – you’ll be close to Chesil Beach and Weymouth. This is also a great area for birdwatching and walking. When you’re not spending time outside, you’ll love this chic, cosy home-from-home. Cook together in the contemporary kitchen before spending evenings watching movies and playing board games.

Fortune's Well

Heated Towel Rail

Shared Pool

Swimming Pool

Wellness & Fitness

Lift Access

Balcony

On the fifth floor of its building, with gorgeous views of Weymouth Bay and its eponymous township beyond, this two-bedroom apartment is a gem in the sky. Enjoy the panoramic vista from the covered balcony, where you can dine alfresco with a view of the historic Portland Castle and the nearby marina, or if you’re hankering for a workout, take advantage of the building’s communal gym and pool. When you’re ready to explore the Jurassic Coast, there’s plenty to do – the D-Day Museum, Chesil Beach and the locally-famous Cove House Inn are just the beginning.

Smart TV

Cot / Crib

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

Library of Books

Record Player

Streaming Services

Luxury Toiletries

Rain Shower

Blender

Espresso Machine

Pod Coffee Machine

Hangers

Ironing Board

Luxury Bedding

Vacuum Cleaner

Laptop Friendly Workspace

Temperature Control

Free Parking On Premises

Private Parking

Early / Late Check-Out Available

Barbeque

Fenced Garden

Sun Umbrellas

Throws

Welcome Hamper

Nice to haves

Safe

Stair Gates

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

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

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

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

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

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

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

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

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

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

Secured Parking

This charming one-bedroom cottage is nestled in a gated development, moments from Weymouth's historic harbour. Tailor-made for two, it may be cosy but you’ll find everything needed for a comfortable stay here. The modern kitchen is a match for any budding chef, but with Hope Square and its abundance of bars and restaurants a short walk away, you can fully embrace holiday mode and dine out with ease. When the sea’s calling your name, Newton’s Cove is a mere three minutes on foot, or you can hike the South West Coast Path, a few minutes from your door. 

Brewer's Cottage

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

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

Sun Loungers / Beach Chairs

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

Trash Compactor

Wine Cooler

Heated Pool

Indoor Pool

Private Pool

Exercise Equipment

Hot Tub

Jacuzzi

Sauna

Sauna / Steam Room

Steam Room

Desk / Workplace

Pool House

Umbrellas

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

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

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

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

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

Private Dryer

Just steps from Weymouth's harbour, you’ll find this cosy three-storey cottage. There's a variety of shops, cafes, pubs and restaurants surrounding this home too. Or spend the day at the beach, just over half a mile away. Further afield, Durdle Door and Lulworth Cove can be reached within a twenty-five-minute drive. Back at this house, there’s a small courtyard to relax in, while inside, the living room has a fire for cooler nights. This cottage is ideal for making the most of your time in this beautiful coastal location.

Harbour Strolls

With stunning sea views from the balcony, this home is a real find. There’s a garden to relax in, too. Set over three floors, you’ll find the sitting room on the first floor and a kitchen and dining space on the ground level – this place is ideal for family and friends. Another highlight of this home is the small, uncrowded beach a two-minute stroll away. Chesil Beach is also nearby, as well as the Isle of Portland with its cliff top walks and rugged landscape. Or for a change of pace, Weymouth’s town centre with its many restaurants, shops and harbour, is 2 miles away.

Portland Harbour Views

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

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

Foosball / Table Football

Games Room

Ping Pong Table

Pool / Snooker Table

This beautiful converted malt store is located in the heart of Weymouth, just a short walk from the beach, restaurants, and cafes. It’s perfectly positioned for a seaside holiday, with the historic harbour a stone’s throw away. This home is an excellent choice for a family as it’s equipped with everything you might need during your stay. Kids will love the games room, and grown-ups will enjoy sipping sundowners on the balcony. There’s also a private courtyard garden where you can tuck into fish and chips in the fresh air. 

The Malt House

Playground

Outdoor Pool

Access to Gym / Spa

Set in a private estate within an extensive nature reserve, this lakeside home offers front-row seats to nature, with all the comforts of modern luxury. There’s space to spread out and unwind, from the open-plan kitchen and cosy lounge with a wood-burning stove, to the top-floor master suite with dreamy views. The games room is a hit with little ones and grown-ups alike, and the lakefront deck is perfect for sunset drinks or a morning coffee. You’ll need to be mindful of some nearby construction to other properties within the estate. However, with a heated infinity pool, spa treatments, watersports, woodland trails and tennis courts all available on site, it’s easy to stay in holiday mode. This is Dorset lakeside living at its best.

Lakeside Dorset

Satellite / Cable TV

Bicycles

EV Charger

In the heart of a private estate, this home is filled with light, warmth and all the essentials you could need for a relaxing retreat. There’s a terrace with a barbecue for alfresco dining and the living room is perfect for cosy evenings by the fire. You'll find the main bedroom comes with an en-suite for optimum privacy and there are two ground floor bedrooms with direct access to the terrace. Plus, there's a communal swimming pool, a gym and a spa available for use throughout your stay. And when it comes to family fun, you can hire water equipment for adventures on the lake and there are beautiful woodland walks.


Keep Looking Up

Nestled in a private nature reserve, this home offers stunning views and a range of luxurious amenities. You can sit back and soak it all in from the terrace, while the living room lends itself perfectly to cosy movie nights by the fire. It’s also family-friendly with plenty to keep the whole group entertained thanks to the on-site heated outdoor pool, spa and children’s play area. You’ll have access to bikes and water equipment for adventures on the lake. Plus, it’s a great base for exploring the beautiful countryside of West Dorset. 

Song of the Lake

DVD Player

This charming apartment is located in the heart of Weymouth. As far as locations go, you couldn't ask for better – the shops and eateries in Brewers Quay, the sandy beach, and the lively harbour are all within easy walking distance. Back home, a cosy lounge is a relaxing spot to wind down from your adventures, while the kitchen has everything you need to create a delicious meal. Both bedrooms are comfortable, though the space around the bed in the main is a tad tight. All in all, it's a laid-back option for a getaway on the Jurassic Coast.

Seashell Snug

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

This apartment offers stunning views of Weymouth's harbour. The location is unbeatable. Shops, pubs, and restaurants are all on your doorstep, while the beach is less than a ten-minute walk away. Back home, the panoramas are the star of the show. You can watch the boats pass by on the small balcony – though there isn't anywhere to sit – or, thanks to the large window, you can appreciate the scenery from the comfort of the sofas. For a Dorset getaway, this ticks all the boxes.

The Harbourscape

DVD Library

Laundry Supplies

Bike Shed

Multiple Sets of Keys

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

For a fuss-free holiday in Dorset, look no further. Not only does this home have everything you need to make yourself comfortable (a cosy living space, a spacious kitchen, stylish bedrooms), it’s situated on an exclusive estate which boasts some excellent amenities. Like free bike hire, a shared swimming pool, and a luxury spa – little extras to make your stay more memorable. There’s a sunny garden too, the perfect place to plan your day over breakfast. Exploring the estate, or adventures along the nearby Jurassic Coast? Whatever you choose – beach day, bike ride, or blissful spa treatment – it’s going to be good.

Navy Nest

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